Rabbi Yaakov Glasser: Finding Ourselves in the Holy of Holies

Transcripts are produced by Sofer.ai and lightly edited—please excuse any imperfections.

Dovid Bashevkin: I am so excited to be sitting here with my friend, my mentor, my rebbe, Rabbi Yaakov Glasser, to talk about tractate Yoma. Welcome, Rabbi Glasser.

Yaakov Glasser: Thank you so much, Dovid. I am equally excited to be sitting here together.

Dovid Bashevkin: This is really a joy because for the first time we get to sit down in person and have a conversation that we really have, I would say, every single year for over a decade, I think, which is before the High Holidays, I get, inevitably, a call from you that is deeply immersed in tractate Yoma, because you are preparing your Shabbos Shuva drasha, the classical presentation that you give before your congregation, which I’m not a part of, you know, like I don’t live where you live, you’re a rav in Passaic, before the High Holidays. I wanted to begin with the following question: You know, a lot of rabbis speak Shabbos Shuva, a lot of rabbis draw upon the themes that come out in tractate Yoma, but a lot of rabbis do not immerse themselves quite as deeply into the traditional, what we call the lamdus, the conceptual framework. They’re not going as deep into the service of the High Priest. Why is it in your process, when you’re getting ready for the High Holidays, you’re like going all the way into tractate Yoma, you’re going all the way into the themes of the service of the Kohen Gadol, of the High Priest? Why not just say a nice idea, just cut to what people are struggling with, which you ultimately always get to, but it’s always anchored in what we call the sugya, it’s anchored in the serious Talmudic discussion with all the commentaries, with all the conceptual analysis.

Why is it important to you in a congregational speech, in a communal speech, that you anchor it specifically in the actual sugya, the in-depth presentation of the Talmud?

Yaakov Glasser: That’s a great question. First of all, I would say that my fascination with the High Holidays in general, as a high point in my rabbinate, as something that I treasure every single year, even though it comes along with so much anxiety in terms of preparation, really begins with my father. My father, growing up, was a chazzan for Yamim Nora’im. That actually had a lot to do with his own journey of discovering Torah u’mitzvos and people who were inspiring to him.

And I always share that growing up, the last hour of Tisha B’Av, my father would always practice Ne’ilah, ’cause he claimed that these were test conditions for Ne’ilah.

Dovid Bashevkin: Wow. ‘Cause he was a chazzan, he was a chazzan.

Yaakov Glasser: Yeah, so he would go through the whole Ne’ilah. And I always say to people that if you’re a teenager, there’s nothing that says churban more than listening to an hour of chazzanus at the end of your fast.

Dovid Bashevkin: At the end of your fast.

Yaakov Glasser: But then this transitioned over the course of Elul, the rest of Av and Elul, the rest of those months preceding the High Holidays, where every Friday night I would fall asleep to him practicing and reciting the entire prayers of the High Holidays. And so it became internalized in a way that’s very fundamental and very meaningful.

And when the season arrives, I look to it from a different perspective than just some of the other aspects of the rabbinate and other aspects of educational opportunities. And I see the chazzan as kind of embodying this experience of the High Priest as he comes to the world of Yom Kippur. And I think like in my own memories of my father davening, should live and be well, you know, I remember him standing in these long, white, adorning robes, the way kittels used to be, like bathrobe material, you know—

Dovid Bashevkin: Sure.

Yaakov Glasser: Yeah. and he had a special chazzan‘s hat, white hat, chazzan‘s hat. Oh, he would wear that hat.

Dovid Bashevkin: Sure he would, I know your dad.

Yaakov Glasser: And, you know, for me, that created like kind of like an experiential dimension that brought me in to this space.

In my own orientation towards the rabbinate and towards teaching Torah, a lot of my focus is on helping to awaken within people their own sense of passion and aspiration for growth, and their own sense of reach to elevation, and become better everything: better people, better fathers, better mothers, better children, better friends, better ovdei Hashem. And that’s a lot of our focus. It’s a growth-oriented shul. And I always share with people, sometimes people come and they’ll join and they’ll get frustrated, because those are the themes that I speak about and that’s how we make even policy decisions in the shul.

It’s not a service-oriented shul, it’s a growth-oriented shul, and that’s always been my orientation. And that’s my own orientation towards Yahadus. I’m also trying to grow. To me, growth has to be anchored in substance, or else it’s ephemeral, and or else it’s contingent on the presence of inspiration, and when the inspiration fades, which inevitably inspiration fades, you’re kind of left with just this emptiness and feeling that like you can’t really keep this up.

When inspiration is anchored in substance, whether or not that substance is like core to the messaging you’re conveying, or whether or not it’s core to the experience you’re creating, so you do two things. Number one is you associate the inspiration with something more grounded and with hard work. Inspiration is often a passive experience for the recipient. You just, “Inspire me.

Come elevate me. Inspire me.” That’s I feel sometimes I get up in shul on Shabbos morning, and I look out at the crowd, and they’re just like, “Okay. This better be good.” Yeah, like, “Do it for me. You know, I’m tired.

I’m this. Keep me up.” You know what I mean? Like, and I always feel like if you’re not ready to do some work here, you’re not going to appreciate what I’m doing. That’s not what I’m doing here. What I’m trying to do is awaken an inspiration within you, and so it has to be anchored in something substantive.

And the teshuvah process, the process of repentance, not the best word, but the evolutionary process of change and growth that is more prominent and more central to this period of the year, to the High Holidays period of the year, I also believe we can’t just be focused on inspiring people to grow, and we can’t even just be focused on giving them advice and like little snippets of guidance and what to do, like tactical growth. We have to help them open up their vulnerabilities and enter into chambers of themselves to kind of really discover like who am I? Where are the spaces that exist? What are the voids that exist, and how can I fill them with meaning and purpose that ultimately emanates from Torah? So, for me, that journey in teshuvah, early on, I discovered that, you know, there’s I think a real misimpression of the avodah, of the service of the High Priest on Yom Kippur, because, you know, it’s often depicted as this is the holiest day, and it’s the holiest person, and it’s the holiest moment, and he walks into the holiest space, and all of this imagery is intended to depict this sense of like restriction, almost, you know, otherworldly—

Dovid Bashevkin: otherworldly rigidity and discipline—

Yaakov Glasser: and sanctity that like we have no access to. Yeah. And this was basically a show that we all watched, and essentially at best, he’s, you know, kind of like a conduit for our growth and our atonement that we need, and so, you know, we’re just kind of watching this show unfold, and it’s unreachable, it’s untouchable, it’s—

Dovid Bashevkin: Passive, in like a way.

Yaakov Glasser: Exactly, and it’s passive. And when you start to open up the sugyos, when you start to open up the topics, you begin to realize there’s such depth of human vulnerability and nuance and experience that is layered into this journey of the High Priest on Yom Kippur. It is anything but, you know, kind of like an otherworldly elevated, angelic experience. It touches so many aspects of the human condition that we experience all the time, and so I started to see it as a paradigm for what growth is really about, and how we can, exactly this, how we can enter into the most vulnerable spaces and fill them with purpose, and with meaning, and with elevation, and aspiration.

And the more I learned Maseches Yoma, and the more I learned these topics, the more I discovered the richness that exists in this space to anchor all discussion about growth.

Dovid Bashevkin: And it’s so interesting, ’cause the way you describe it, that’s what brought me to your Torah. Every year, I look forward to it. What are you thinking about, where’s the topic? And you pick different points in the avodah, where at this point after you’ve been doing this, you’ve been a rav there for Has it been 20 years?

Yaakov Glasser: Over 20 years, a little over 20 years.

Dovid Bashevkin: For 20 years, and each year you pick a different point. I find myself like the way that you weave together actual, you know, disputes in the Talmud and the commentaries, and then you build this canvas upon which we’re able to discover parts about ourselves, has been really a central point of my Yom Kippur, High Holidays experience for so many years. And what I want to do today is actually exactly that. I don’t want any of our listeners to panic, we’re not going to repeat five different Shabbos Shuvah derashos, we would be here probably till next Yom Kippur, we’d be here for quite some time, but I do want to kind of pull out in order, going through the process, and pull out some of the key themes that you’ve touched upon, and maybe in a very cursory, but not just the idea that you land on, but how you got there.

And I think the place to begin, which is really before the actual Yom Kippur service itself, is the Kohen Gadol before the actual Yom Kippur experience, and this is the opening of the entire tractate, is secluded, and he’s secluded in a very specific room which is called the Lishkas Parhedrin, which was kind of a chamber that was adjacent to the Temple, the Beis Hamikdash, and he would stay there by himself for seven days. And you’ve discussed both the significance of something unique about this room, as well as the larger purpose of why the Kohen Gadol stays alone. Explain to our audience, what is the significance number one of this chamber, what made it unique where the Kohen Gadol is staying secluded? And what are we to make of the seclusion process itself?

Yaakov Glasser: The Lishkas Parhedrin is the subject of a discussion in the Talmud with regards to a mitzvah that we’re very familiar with, which occupies the doorway of every home, which is the question of placing a mezuzah on the doorway. And the Talmud discusses the question of whether or not this space, because fundamentally a mezuzah is required on a beis dirah, a place where someone lives.

So this is a very temporary dwelling. This is not a permanent residence for this individual. Spends the seven days there, and that’s it. Does this room require a mezuzah? So that discussion seems to be a very technical, halachic discussion of trying to analyze the principles of what are the required elements for a room to satisfy the expectations for a mezuzah.

But the Gemara has in the context of that discussion, the Gemara writes that we should affix a mezuzah, and the reason the Gemara provides, I believe it’s in the name of Rabbi Yehuda, is shelo yomru chavush beveis ha’asurin.

Dovid Bashevkin: That people should not say that the Kohen Gadol is being locked away in prison.

Yaakov Glasser: In a prison, exactly. And the question obviously is why would anyone think this? This is one of the holiest individuals in our entire community.

He’s preparing for such a noble and sacred—

Dovid Bashevkin: And we know Yom Kippur is coming.

Yaakov Glasser: Right, like who’s starting this rumor?

Dovid Bashevkin: There’s no social media for like conspiracy theories.

Yaakov Glasser: Exactly, like maybe he’s been locked up, you know, maybe he did he did something he shouldn’t have, and it’ll be on a different podcast, you know? So why would one imagine that he’s chavush beveis ha’asurin? And the answer is because we know that we’ve been restrictive with his movement, and we’ve been very, highly choreographed in terms of what he can and cannot do and what he’s supposed to be doing right now. We’ve taken control of his life.

And from the outside, restriction and patterned control could be perceived as something that’s imprisoning. And if we kind of like expand that metaphor to our own lives, you know, much of Jewish life requires of us to anchor our behavior in patterns, in expectations. There are lots of restrictions of what we can and cannot say, what we can and cannot eat, what we can and cannot look at, and what we can and cannot do.

Dovid Bashevkin: We’re all secluded in a certain way. Jewish life is deliberately pulling you out from the daily rhythm of the world. We have obligations and responsibilities.

Yaakov Glasser: Exactly. And we have to come to terms with the fact that very often, especially in a generation like ours, which elevates the values of autonomy, and independence, and free choice, and that could be experienced by us—

Dovid Bashevkin: Optionality. I want to preserve the options, yeah.

Yaakov Glasser: Exactly, I want to be able to do what I want. And if I want to choose religious life, I want to choose religious life.

The notion that this is expected or required, or in the words of the Maharal, you know, when he discusses the imagery of the mountain hanging over your head at the time of the giving of the Torah, that there’s almost a coercive, compelling truth to this reality that, yeah, you could choose to do the wrong thing, but like this is the right thing. So that does, in our world, in our experience, often feel very constrained. And so I developed kind of like this imagery of the experience of watching the Kohen Gadol in this condition, and how it relates to ourselves, and our own religious life, and our own religious conditions. And by the way, this extends beyond Torah and mitzvos: the social expectations that we have of ourselves in our community, the economic expectations we have of ourselves in our community, all sorts of aspects of religious life, you know, feel like the optionality has been limited.

And I can’t live in the way I want. Our family did two major RV trips, you know, like family RV trip, like I drove a 32-foot RV across the country from Passaic to LA, and another one, 2,500 miles around the Pacific Northwest, and you go to these RV parks—

Dovid Bashevkin: Consult your local RV dealer before planning a trip for yourself.

Yaakov Glasser: Yeah. It’s like I tell people who tell me they want to do this, you know, I say to them, “You want to see what your marriage is really made of? Live with your family in a room in a car for two weeks.” So baruch Hashem, thank God, it was a beautiful experience.

And you meet people along the way that you would not otherwise meet, and it was one of the goals of the trip. I wanted my children, who are growing up in a more limited and sheltered environment, to kind of breathe and see other kinds of people in the world, and it was fascinating. And you see people who live like this, and you’re looking at this and you’re like, “Wow, you know, what would it look like to just be able to go wherever I want to go and drive wherever I want to drive and stop wherever I want to stop and live like this?” And you realize like very challenging to live like this in a world where we want a minyan, and where we want a Jewish community, and where we need schools, you know, for our kids, where we—

Many of us do experience aspects of it as chavush beveis ha’asurin. That we’re imprisoned. We’re imprisoned. And you look from the outside, it seems like that’s imprisoning. And the notion of affixing a mezuzah, which conveys the fact that this isn’t only a space of restriction, this is also a home, where the values and ideals that give rise to the focus that inevitably involves some restriction, or a lot of restriction, that too can be a source of tremendous religious elevation, and energy, and meaning and purpose. To affix, you know, what’s in a mezuzah? Shema Yisroel, hear O Israel, God is our God, and it talks about the love that we have for God and the opportunity that we have for mitzvos, and to place that mezuzah on the Lishkas Parhedrin so everybody sees that this man, who it looks like his life is being so controlled, is actually encountering an opportunity for self-actualization and encounter with elevated opportunities for meaning and purpose that are transcendent and that can only be created when you’re able to kind of filter out the noise of life and create that space of the Lishkas Parhedrin.

So that’s one of the underlying messages that this is intending to convey. So I would take the congregation through the topic itself, you know, understanding, you know, the independent analysis, you know, of that, right?

Dovid Bashevkin: Yes, mezuzah, no mezuzah, or where.

Yaakov Glasser: Exactly, and what are the different, and then at the same time, then lift it up into our own human experience.

Dovid Bashevkin: And it’s such a beautiful introduction to Yom Kippur itself, where we’re reflecting on all of our obligations, reflecting on all the missed opportunities and missed expectations.

It’s very easy to cascade into this feeling of like, get me out of this jail, get me out of this prison. And there’s this reminder, as we kind of embody the Kohen Gadol, of like, don’t forget the mezuzah that’s on your wall. You can transform these obligations into a home. You can transform all of these requirements and commitments.

If they’re done in the with the right sense and with love, this can become a home for yourself and for your family.

Yaakov Glasser: Right. And I spoke about what are the mezuzas that we place in various aspects of our lives so that they don’t over time begin to feel, and that we make sure to layer into that experience opportunities to connect with its elevating nature. We don’t take that for granted.

Then that would shift into more of the practical, you know?

Dovid Bashevkin: Sure. This is a beautiful idea, and it’s an introductory idea because this is where the Kohen Gadol prepares, and it reimagines that solitude in many ways.

Yaakov Glasser: Now And the High Holidays Don’t view the High Holidays as a time of restriction, like, we’ll joke, right? Oh, we can’t talk loshon hora, it’s Elul. As soon as we can get past this season, then we can start sinning again, you know, like don’t view it that way.

View it as an opportunity. But don’t be in denial. A lot of this is about validating the challenges of living religious life, and I think that’s important for ourselves and for our children.

Dovid Bashevkin: So the Kohen Gadol comes out of the Lishkas Parhedrin, and I want to start entering into the day of Yom Kippur itself.

As we mentioned, throughout the day on Yom Kippur, the Kohen Gadol goes to the mikveh a total of five times, and he’s kind of toggling between the regular daily service, or maybe a more typical Yom Tov service where he’s wearing the eight garments, and then the specific Yom Kippur service where he wears that more simplistic four garments of the Kohen Gadol. So the day begins where he comes out of the mikveh for the first time, and he does kind of the daily operations. So it’s just the Kohen Gadol doing the service, but this part of the service, he’s wearing the eight garments, the Urim V’Tumim, which is the stone that you’re probably familiar with if you’ve ever seen a picture of the Kohen Gadol, and this part is kind of typical. It’s the way that you start any day.

And it’s only after the second time he goes to the mikveh to change into the four garments that the specific service of Yom Kippur truly like begins. Like this is new, we don’t do this any other day. And at the heart of this service is one of the first thing that the Kohen Gadol does, is he first has like a personal bull that he confesses over, for himself, for his family. And then right after This is like the part that I think is so strange.

I’m sorry, this is before the bull, even, is there is a lottery over these two goats. Like at the heart of the Yom Kippur service, and it kind of stretches throughout this middle chunk of the day, are these two goats. One is a goat, the what’s called the se’ir LaHashem that is then sacrificed and the blood is sprinkled in the Holy of Holies, and then there is a second goat that is known as the scapegoat that is pushed over a cliff way outside of Yerushalayim and the temple, and the way that they decide which goat is which, because they’re supposed to look alike, is through a lottery. Explain to me, why is this lottery significant? Like they had to do the lottery, the Kohen Gadol can’t just pick, just have one like, “Oh, this is a goat, you know, I’ve known him for so long, we grew up together, been in my backyard, this is the one I’d like to bring into the Holy of Holies.” How did you approach this question of what is the significance specifically of choosing which goat is which through a lottery?

Yaakov Glasser: It’s inspiring to listen to you chart the course of so many meaningful stopping points, even amongst everything you said.

Yaakov Glasser: You know, the whole notion, there’s a big discussion in the commentaries: how much of the regular daily service that’s not Yom Kippur-oriented gets handed to the high priest, as opposed to being done by the regular priest? That’s a big discussion in the commentaries, as far back as the possibility that one of his jobs is to actually clear off the ash of the previous day. So you imagine, it’s Yom Kippur, the rabbi comes into shul before Kol Nidre, and one of the things you find him doing is he’s just sweeping the shul—

Dovid Bashevkin: the floor, yeah—

Yaakov Glasser: putting the machzorim back on the shelves. Yeah, like that, you know? So, this whole notion that the Kohen Gadol is vacillating back and forth from accentuated sanctity to more regular normative religious life is a big part of Yom Kippur, because the Torah and Hakadosh Baruch Hu is not interested in Yom Kippur exclusively being—

Dovid Bashevkin: like this transcendent escapism.

Yaakov Glasser: Right, this utopian, you know, like reality that’s contrived and manufactured, where we exist in this higher spiritual world.

Even the back and forth with the garments, it’s critical that the Kohen Gadol is taking the Jewish people back and forth from elevation to normative, because ultimately the goal of Yom Kippur is not to escape the normative for this high spiritual experience that then ends. The goal is for Yom Kippur to influence the day-to-day.

Dovid Bashevkin: Exactly.

Yaakov Glasser: So that’s why the high priest also has to bring the regular normal Shacharis korban, right? You know what it would translate into?

Dovid Bashevkin: He’s cleaning up the ashes.

Yaakov Glasser: Imagine the chazzan for Yom Kippur, he also does berachos in the morning, you know what I’m saying? Like, no!

Dovid Bashevkin: You hire some fancy-schmancy incredible singer, and he’s the one doing Birchas HaShachar.

Yaakov Glasser: Exactly, you come in and he’s making the Asher Yatzar for the for the congregation at the beginning of the day. That was what the Kohen Gadol did, because God didn’t want the people to look at him as some sort of distant. Even the fact, and you brought this up, it’s such a beautiful point, when we think about leadership, we generally think about sacrifice and commitment to the klal, to the community, and then ultimately also to make some space for the family and for the personal.

Dovid Bashevkin: Yeah.

Yaakov Glasser: It’s not how it goes for the Kohen Gadol. It’s reversed. It starts with the personal.

If you can’t reach yourself, if you don’t know who you are, if you don’t know what you bring to this as a human being, if you don’t know what your family conditions and your context, your struggles and your realities brings to this, how in the world are you going to carry the struggles and the dreams and aspirations of the larger Jewish people?

Dovid Bashevkin: And this is literally the first thing the Kohen Gadol does in those white is he confesses, it’s a personal confession, over his personal bull that belongs to him.

Yaakov Glasser: Yes, because we don’t want a Superman. We want a real person who’s elevated themselves to That’s who represents us, that’s who embodies us, and that shows us what we could be. We want to be able to look at this Kohen Gadol We may never be able to be a kohen or a Kohen Gadol, but we can aspire to some of the sparks of greatness that are revealed through this process, and that, I think, is why it’s so critical.

That’s why he begins with his own vulnerabilities.

Dovid Bashevkin: Exactly. You’re a person. You’re a human being. You also did things wrong, rabbi, you know? And before you start talking to everybody else and representing everybody else, maybe you should get it together, and maybe you should figure yourself out.

Yaakov Glasser: I want to share with you, and then I’ll get to the to the choice: when I prepare a Everybody has different styles and methodologies, processes—

Dovid Bashevkin: sure, in preparing a drasha.

Yaakov Glasser: One of the things I like to do, I can’t say I do it every week, but I do it many weeks, is, how does a rabbi choose? How does a rabbi decide, when you’re sitting in shul and he gets up and he starts talking, how did he decide what to do? There’s so much Torah, there’s so many topics, there’s so many everything.

Dovid Bashevkin: Talk about anything, sure.

Yaakov Glasser: So what I like to do is, I take a yellow pad, and I make a big line down the middle. And on one side, I write all of the issues and struggles that I think, based on my conversations and my meetings and my everything, I think that my congregants, when they walked into shul this morning, what’s on their mind? What’s their issue? On the other side, independent of that, I write what’s on my mind. What’s affecting Yaakov? What were my struggles? What are my challenges? What are my issues? What are my aspirations? Anytime the two line up, I draw a circle. That’s going to be the theme, because that’s something that will speak to the people and also will come from my heart.

Doesn’t always work.

Dovid Bashevkin: Yeah.

Yaakov Glasser: Sometimes you have to talk about something that relates to the people that’s not bothering you. Yeah.

Sometimes my congregation has to suffer through my issues.

Dovid Bashevkin: Yeah, and it’s fine.

Yaakov Glasser: No, they’re like, “Yo, we’re really okay. You know, like, we’re really not struggling with the fact that we didn’t become a Rosh Yeshiva, like, you know, I guess that’s what we’re going to do now.” You know, like, and sometimes they just have to accept that.

But for the most part, that’s where I try to bring the two together. And I think that’s personified by this: first deal with yourself, where are you? This moment of goral, the lottery, a lot of the discussion in the commentaries relates to certain technicalities about what aspects of that lottery experience required the Kohen Gadol, required the high priest. And there’s a distinction made between the actual choosing of the lottery and the next step, which was placing the indicator of what was chosen on the animal itself. One might imagine that’s just a technicality.

Dovid Bashevkin: Meaning you have these two kind of like, they’re literally kind of like this, like my coasters. Right. And you’d pick up, one would say LaHashem, one would say La’azazel, and then you’d have to place them on each goat.

Yaakov Glasser: Exactly. So the Gemara talks about the fact that nesinah, that placement, is also, potentially, a form of avodah. And in that regard, we explored a lot of the underlying principles and concepts related to this part of the procedure of the goral, but ultimately, what emerged was, what, it almost seems like a kid’s game. Choosing lotteries, like what are we doing? Like what—

Dovid Bashevkin: Yeah, and they’re both the same, they look the same.

Yaakov Glasser: Right, everything has to be the same, like what are we doing? And I think the answer is that, you know, when we look at life, we very often experience the circumstances of We were born into a certain reality, given a certain set of talents and abilities and challenges.

Things happen way out of our control. And a lot of our kind of positioning in our own personal life is relating to the fact that we feel largely I don’t want to say the victim of circumstance, but the product of circumstance. And, you know, we look at other people’s lives and we say to ourselves like, wow, you know, their circumstances seem to produce And it’s not always jealousy that like the Torah talks about, you know, we’re jealous of their stuff. Sometimes we’re just jealous of their condition in life.

Dovid Bashevkin: Correct.

Yaakov Glasser: Wow, it seems like they got it together, like—

Dovid Bashevkin: Nothing bad happened, they didn’t look like any cataclysmic struggles.

Yaakov Glasser: And then you look at your situation and you’re like, well, maybe I can get what they have. And then you realize, not really.

Like, you know, you were born into this family and you married this person and these are your children and this is where you live and home. And you can’t always just like change everything, you know? A lot of life feels like everybody was kind of like—

Dovid Bashevkin: Like in the lotteries, I think of the bowl.

Yaakov Glasser: Like in camp, you know what I mean? Like, you know, you put your hand in the thing, you pull out a ticket. The kids are all sitting there, “Hey!” You know, and you’re just like, “What?” And then one kid’s like, you know, and then in our shul, we buy these prizes at, you know, Amazing Savings, so the kid comes just like running up to get this $4 toy, you know—

Dovid Bashevkin: A water gun or whatever it is, yeah.

Yaakov Glasser: Right, you know, and all the other kids are watching and they’re like, we were all here.

Dovid Bashevkin: Yeah.

Yaakov Glasser: We were all part of this program. We were all present. Why did he win?

Dovid Bashevkin: I this analogy, by the way, it sounds so small, bringing my son to parent-child learning and watching his face be absolutely crushed, because Bashefkins have a curse, we never win lotteries. It goes back generations. We don’t win these things. We don’t win raffles, ever.

That’s always my friend Yoni Sonnenblick wins all raffles. It’s like painful. And you see that, like, I was here, I had the ticket, it’s just like my number was wrong.

Yaakov Glasser: And you’re sitting there, and it’s inescapable that some kids win more than others.

Dovid Bashevkin: Yes.

Yaakov Glasser: I don’t know anything about the laws of probability and how to calculate those things, but I could tell you that at a parent-child learning program, there are kids who win more often. Yes.

You know, and you’re just watching this unfold. And on a day where we’re trying to reach the essence of ourselves and our sense of purpose, coming to terms with our standing and our condition that we all come into life looking the same, we all come into life like with this, you know, babies just crying and whatever. Yet that’s what the two goats, they look the same, they seem the same, but then it’s the circumstances and providence of life that ultimately results in one finding themselves in one condition and one finding themselves in another condition. And the process of the Kohen Gadol bringing intentionality and empowerment and I don’t want to say control, but to kind of establish, okay, where are we going from here, that to me is what’s manifest in that moment where he says, “And now this is the way this is going to go, this is the way that’s going to go,” placing it on and saying, “Okay, now we have to deal with your trajectory and your destiny.” Be sacrificed in sanctity for the Jewish people, and that ownership of your life circumstance as number one, not being forever experienced as a goral ends. And that moment of intentionality is when that may be how we got here, you know? We may have gotten here through what we experience as a goral.

I’m not denying the fact that from God’s perspective, everything’s choreographed, everything’s intentional. And of course, we believe in divine providence. But we don’t always experience it that way. We spend our whole life The fact that we know it’s intentional is empowering, because it allows us to do the next thing we have to do, which is to say, “Okay, but this is where I am.

This is my lot. And that means that there’s a calling for me. There’s a nesinah, there’s a placement for me. And I have a job and a role, and it matters.

And nothing can move forward without it.” And, by the way, there’s a lot of discussion in the commentaries, what happens if something happens to one of these sacrifices, the degree to which they could be replaced they’re me’akev each other, right? They’re interdependent on each other. Right, me actualizing my potential and not trying to chase after your potential is actually critical to the ultimate success of the Jewish people.

Dovid Bashevkin: These two goats might be linked, and they both need to reach their destination—

Yaakov Glasser: which is unique to them. And that moment of transition from feeling like, it’s feeling—

Dovid Bashevkin: like It’s all lottery, it’s the happenstance of life, the chaos of life.

Yaakov Glasser: To feeling like, “Okay, but what do I do now?” And that starts to chart the course. So as the Jewish people watch this lottery and then they watch the Kohen say, “Okay, we have no idea, only God knows why this one was chosen this way and that one was chosen that way. And only God knows why I was privileged to grow up in Los Angeles, California and you, nebech, grew up in — We don’t know why, only God knows. But now, like, now is the moment of nesina, now is the moment where you guide it to the next What do you do with your life?”—

Dovid Bashevkin: Absolutely beautiful. You know, I actually remember when you put that together, because you opened my eyes to this procedure of the two goats and this beautiful juxtaposition of the lottery, but also it doesn’t end with the lottery. The lottery does end, but then you’re doing something very intentional: you’re taking what you pick up and that’s a part of the service, placing it on each goat, taking a little bit of agency, adding agency juxtaposed right next to that lottery. But you introduced me to what I think might be the personality I feel most connected to in all of Tanach. And this personality does not even have a formal name.

I don’t think we’re ever given a story of anybody who participated in this role with a name, but in the Torah, and this appears in the sixteenth chapter of Leviticus, and it has to do with what happens next in the ceremony, which is you take the goat, the scapegoat, the one that’s to be pushed off a cliff, and you give it to this personality that is described as the ish — it means a person, a man, with an ayin–tav–yud means like of time, like it’s a very The commentators are like, “What is the translation?” And this person takes it not just out of the Temple, but out of Jerusalem. It’s going on a walk. And the Talmud opens up the possibility that he might have to break his fast to get there. Like this person is not is not doing this Kohen Gadol seclusion, sanctity.

This person is going through the wilderness in the Middle East to push a goat off of a cliff. Explain to me who is this person, what is their role, and how can it be that on Yom Kippur where there is such a focus on the Kohen Gadol, and there’s such a focus on the sanctity of the Kohen Gadol, and that everything needs to be done by the Kohen Gadol, and we have this like cameo appearance, the one other person who gets involved in this service, and this is the ish iti, the man of time, and they’re like going out into the wilderness and possibly even like not even properly keeping Yom Kippur?

Yaakov Glasser: It’s a fascinating aspect. It relates back to what we were talking about before all throughout the avodah, throughout the service, constant duality of hyper elevation and at the same time, the confrontation with what’s wrong or vulnerability. An interdependence is created between the Kohen Gadol and him.

The Kohen Gadol is not allowed to move forward in certain aspects of this service till that ish iti is well underway. His role is to take this goat that somehow encapsulates the failures and sins of the Jewish people out into this desert and ultimately to throw it, guide it, push it off the cliff. That process itself is fascinating because, generally speaking, we’re pretty careful with how animals lose their life. Context of Judaism, tiniest nick in a knife that’s used to slaughter an animal That could—

Dovid Bashevkin: prolong the slaughter process.

Yaakov Glasser: Yeah, that makes the entire animal not kosher. And suddenly we’re like, “Throw it off the cliff.” There’s a lot of discussion even what the status of that experience is. Is that animal viewed as the refuse of the original dynamic and it’s just meant to symbolically kind of export our sins outside our world, outside our life, or does it itself have the status of a sacrifice, of a unique sacrifice which is discussed by the Rishonim—

Dovid Bashevkin: where the pushing of the cliff may be how this korban is slaughtered, meaning is a technical slaughtering, it’s just done in a very unusual way.

Yaakov Glasser: Exactly. And that’s because I think a lot of this journey of this ish iti and the way in which this particular sacrifice is offered is intended to convey our sin and our failures don’t stand exclusively as counterproductive, counter things we do right.

Dovid Bashevkin: That we get pluses and minuses. Right. If I did five mitzvos, so I’m plus five, and three aveiros, so now I’m back at two.

Yaakov Glasser: Yeah, people have a very transactional approach. I like to refer to it as like Skee-Ball Judaism. I know Skee-Ball is not as popular anymore.

Dovid Bashevkin: No, I love Skee-Ball. I’m very into it.

Yaakov Glasser: But like when we were kids, you know, you play Skee-Ball, you get the tickets—

Dovid Bashevkin: Yeah. and then very ticket obsession if you’re going like Dave Buster’s or one of those places.

Yaakov Glasser: Exactly. You take the tickets and then, you know, with 40,000 tickets, you can get like a an even cheaper prize from Amazing Savings. But that was that was a big driver, and it was very clear at the end of the day how good you were at Skee-Ball because you had the tickets, you know.

Dovid Bashevkin: Yeah.

Yaakov Glasser: And I think a lot of people experience Yiddishkeit that way. They’re trying to accumulate points.

Dovid Bashevkin: Yeah.

Yaakov Glasser: Mitzvos are points, aveiros you lose points. Yeah. And we’re trying to figure out like what, you know, Who’d have—

Dovid Bashevkin: the most points—

Yaakov Glasser: at the end of their life? And it’s clear that’s not the orientation of the Rishonim. Rambam himself says in the laws of teshuvah, in the laws of repentance, that if a person, we are all assumed to emerge from Rosh Hashanah as beinonim, as kind of half-and-half, that, you know, we should look at ourselves as if, you know—

Dovid Bashevkin: Always we’re 50-50.

Yaakov Glasser: We’re 50-50, so we could go either way. The solution to that clearly should be, so just do some extra mitzvos—

Dovid Bashevkin: Yeah.

Yaakov Glasser: and you’ll be done. Do one more and you’ll tip the scales. That’s not what he says. He says, do teshuvah, which is really hard.

That involves introspection, and that involves—

Dovid Bashevkin: Self-transformation.

Yaakov Glasser: self-transformation.

Dovid Bashevkin: You’re at 50-50, you just need Come on!

Yaakov Glasser: Yeah, exactly. Like go on a chesed mission, like, you know what I mean, and be done with it.

And the answer is that we’re not trying to solve a transactional problem. There’s no way we could possibly account for the divine calculus of everything. Pirkei Avos tells that. We have no idea what all these mitzvos are quote-unquote worth in our accumulation of reward and punishment, which is very real.

All we can do is relate to these dimensions of our religious life as core to our growth and our ability to ultimately achieve what we were put here to achieve. And the degree to which we fail, it takes us away from that focus, from that ambition. And so we have to deal with that, we have to counter that, we have to elevate ourselves, we have to recognize that, we have to apologize for that, we have to find ways to improve and be better. But embedded within all of those mistakes, and even more than mistakes, that goat is carrying, is also all of the potential growth that can emerge from failure.

Therefore, it’s not just like the Kohen Gadol takes this animal and, you know, it becomes like the ultimate symbol of our sins, let’s just sacrifice this.

Dovid Bashevkin: Throw it out of here, get it out of here.

Yaakov Glasser: Right. It becomes part of a journey of a person, of a human being who himself, you know, kind of personifies that struggle, and those sins become themselves sacrifice.

And what happens to them becomes core to the overall process itself.

Dovid Bashevkin: It’s not just taking out the garbage.

Yaakov Glasser: This is a part—

Dovid Bashevkin: of the service.

Yaakov Glasser: Exactly. Exactly. And the reason is because embedded within those failures is tremendous opportunity for growth, the concept of yeridah letzorech aliyah. Sometimes we have to go down in order to come up. I know you’ve you’ve mentioned many times in your writings and in your shiurim, podcast, the famous letter of Rabbi Hutner, Sure.

you know, who discusses the pasuk, sheva yipol, sheva yipol tzaddik vekam.

Dovid Bashevkin: The plain meaning of that is that the righteous will fall seven times, but at the end—

Yaakov Glasser: They’ll get up.

Dovid Bashevkin: And Rav Hutner writes in his 128th letter that is a misunderstanding.

Yaakov Glasser: Yeah, that really what it means is you get up because of the fall. The fall is part of this. And I think that Yom Kippur, when it, you know, we think about atonement, we think a lot about like just getting rid of it all.

Dovid Bashevkin: We want to be a blank slate.

Yaakov Glasser: Right, it’s not about a blank slate. It’s more than that. It’s about elevating these as potential catalysts for growth and change. And it’s about your struggles becoming a source of you finding strength in yourself. And it’s about the things that you find most difficult that ultimately, through that process of confrontation, and effort, and sacrifice, persistence, that you can discover dimensions of greatness in yourself that you didn’t even realize you had.

And so this ish iti, I think, is kind of like the hero of the Jewish people in the sense that, like, there’s a piece of every one of us that’s that’s with him as he kind of carries these sins off the Mikdash. The goal is atonement. The goal is the clean slate. But the question is the clean slate, you know, accomplished by just expunging everything that’s wrong—

Dovid Bashevkin: Just erasing all of— the—

Yaakov Glasser: the Right, or is it part of the journey? And for him, it has to be part of that journey.

And even the journey itself, as you pointed out, can come with compromise in areas of halachah that are understood and presumed to almost be inevitable and not undermining to his ultimate mission, because we’re put here as imperfect beings, and part of Yom Kippur is to redeem those imperfections and elevate them as a space from which we can grow.

Dovid Bashevkin: I mean, it’s such a radical idea. It’s part of the reason why I never liked the translation scapegoat, because when you translate the se’ir la’azazel as a scapegoat, it makes it sound like it’s the first possibility, that it’s just like this is the symbol of our sins, and we just like, out of sight, out of mind. We want this out of here.

Like this is who we’re going to blame. And what you’re talking about is an extraordinarily radical idea that’s recognized as a radical idea by the commentaries, where it almost says, and I want to be careful with the language, but through the process, the full fulfillment of teshuvah, we are able in a way to sanctify our sins by recognizing that our imperfections are a catalyst for growth.

Yaakov Glasser: Yes, and we see that all over life.

Dovid Bashevkin: Yeah. And Like dating and, yeah.

Yaakov Glasser: Yeah. One of the things that always comes up when families are going through a struggle or a trauma or a difficult moment, whether it’s loss or a divorce, is this fear, stigmatizing—

Dovid Bashevkin: What’s going to be with the shidduch? Are people going to want to marry this person, date this person?

Yaakov Glasser: Yeah, and I, and I tell people all the time that when you talk to young people who’ve been through challenge, trauma, they have so much more nuance and sophistication. Again, assuming it’s been processed properly.

Dovid Bashevkin: Sure.

Yaakov Glasser: You just allowed the trauma to percolate, affect their life, then—

Dovid Bashevkin: Wipe you out, for sure.

Yaakov Glasser: It can, but, you know, I, over the course of Rosh Hashanah, we had a number of single moms over for meals. That was kind of what we did for Rosh Hashanah, in tribute to Rabbi Hauer, who this was a big focus of his.

Dovid Bashevkin: Sure.

Yaakov Glasser: I’ve been thinking a lot about him, his yahrtzeit, and I was so impressed. They had a confidence and a, and a nuance and a sophistication. I’m sitting there and I’m thinking to myself, “This is gold! This is gold!” You know, like, someone would be lucky to have this person as a life partner.

A child would be lucky to have this person as a father or as a mother who gets that life is not simple and has developed the fortitude, the ability to, you know, deal with challenge in life and failure in life. I personally experience that all the time. Not just sin as sin, but sin as a broader category of, you know, when we don’t feel like we’re able to do everything the way we want to be able to do it. You know, in my own learning, some people, when they learn Torah, brilliant, and they catch on to everything immediately, very quick.

I’m very grateful to Hashem. He gave me a lot of gifts in teaching Torah, but one of the gifts He gave me is I don’t catch on so quick. It takes me longer. I get it eventually, but it takes me longer to read the Gemara, to understand the Gemara, to understand the Tosfos, to understand, you know, and here we are in Daf Yomi, Eli, and they’re going to be people who feel like, “Oh, everybody should be able to move through this, you know, at a page a day, and it’s no problem, and it’s not—” Some people, it comes very naturally, very quickly.

Some people go slower. And this was a form of enormous existential tension within myself in my formative years, as I watched my friends and my chavrusas, they always— It’s like this—

Dovid Bashevkin: jet off, yeah.

Yaakov Glasser: They always got it, you know? And then I started to realize that, like, the gift of being able to be insightful and creative sometimes requires the ability to be a little slower, a little more incremental, because when you walk through the forest a little slower and not running so fast, you see more. You see more texture, you see more detail.

You actually don’t allow your mind to just justify that, “Oh yeah, that makes sense. That must make sense.” No. Like, did that make sense? You see questions and issues and problems that other people don’t see, and it creates so much more nuance. In life in general, ish iti moments, the moments that you’re dealing with struggle, the moments that you’re dealing with failure, that often look like they are independent of spiritual accomplishment and achievement, I think the message of Yom Kippur is that is also part of the avodah.

That is also consecrated. Yom Kippur can’t just take place in the Kodesh Hakodashim, the Holy of Holies. Yom Kippur also takes place out in the middle of the desert, in the barren, and the most beautiful Gemara, one of the most beautiful Gemaras in the world, talks about after Yom Kippur, and it says how the Kohen Gadol and the ish iti would meet each other.

Dovid Bashevkin: Would meet each other.

Yaakov Glasser: I almost feel like the end of Yom Kippur, that has to happen within each and every one of us. The piece of us that went through Yom Kippur and davened Ne’ilah, and then after Ne’ilah is over…

Dovid Bashevkin: It’s like you give a big hug to…

Yaakov Glasser: It’s like you give a hug to the piece that’s that didn’t go through Yom Kippur the same way, and the piece of us that has to take us through the next few weeks, the rishon la’avonos, you know, the beginning of the, you know…

Dovid Bashevkin: Yeah. Yeah, I’m so happy you mentioned that. Such a profound encounter of this ish iti and the Kohen Gadol meeting after Yom Kippur and really having that integration, so to speak, of self, representing— That—

Yaakov Glasser: wholeness is, that’s who we are. That’s what it means to be a human being. God didn’t create us as angels. He created us imperfect, and He created us with work to do. Hardest part of life is figuring out what’s your work, and to fail and succeed at it as best you can.

Dovid Bashevkin: Kind of one of the central components of Yom Kippur, the first time that the Kohen Gadol enters into the Holy of Holies, the first time is he comes in with incense, with the ketores.

And it’s very deliberate. There actually before Yom Kippur, we make the Kohen Gadol specifically swear that he’s going to do this properly. And there’s this moving scene where the people who make him swear and the Kohen Gadol then afterwards both turn to the side and they start to cry, that like, this is where we are, that we can’t be sure if the service of the Kohen Gadol on Yom Kippur is going to be done properly. But kind of the first entry, and in a lot of the imagery of Yom Kippur, it’s specifically imagery of the Kohen Gadol with this incense.

And I just wanted you to share maybe a word, because we’ve spent a little bit of time and people are more familiar with sacrifices, you know, animal, they might not feel as relevant or connected to it. That’s a very distant and tough to appreciate conceptual idea. But the idea of incense, for a lot of people… people inside the Holy of Holies is strange, you know, unless you’re like a ’60s child, you know, and you went to Woodstock and incense is what you would light before your parents came into your bedroom so they didn’t know what was going on in there.

But we’re not really so familiar why is it that first entry, like the creme de la creme entry, is not with the sacrifice, not his personal bull, but specifically with this incense, this fragrant smell and aroma, a very complicated practice to do, that he goes into the Holy of Holies with for the first time.

Yaakov Glasser: It’s interesting you mentioned this confrontation that happens to make sure that he does it right, because that has to do with a lot of the historical controversies over the course of generations that other sects of Judaism had other interpretations of how this specific service should take place. One of the reasons they have to make him swear, you know, if you’re worried, so like do what we do with every kosher restaurant in the world, like have somebody in there to make sure he does it right. And the reason we can’t do that is because the Torah says that when the Kohen Gadol enters the Holy of Holies, he has to do so alone.

There’s a lot of discussion in the commentaries: What is the nature of that requirement? Some interpret the nature of that requirement is that he has to experience loneliness. It’s on him. And the reason it has to be done in solitude is because part of what we’re trying to convey and project is the uniqueness of the individual. In response to our presumptions of what others are looking for, at this most sanctified moment, God is saying to the Jewish people, “I just want to be alone.” And I think for each of us, to try to kind of reach that moment of solitude, to kind of peel away everybody else.

He walks in there with this ketoras. One of the requirements for this incense is that it has to completely envelop and fill the room. And in fact, a ingredient was added that specifically ensured that it would saturate the entirety of the room. So it wasn’t just like smoke would fill the room.

And so there’s a lot of discussion, again, is that a technical point, or is there something more fundamental about that moment? And assuming there is something more fundamental about that moment, what really is being conveyed here is that this experience of encountering God—Gemara talks about, like, saw, like, the image of God—this takes place within a cloud of incense because encountering God doesn’t just happen in a space of clarity. Very often, our strongest moments of faith emerge from spaces that require us to kind of stretch, and move, and take a leap of faith. And so the notion that this is the moment where he comes closest to the divine presence, of God himself, that takes place in a fully consumed cloud, is expressive of the fact that even when we live in a world and in a life where it’s hard to see, like, if you’re present, and you’re there with purpose, and you’re looking for it, you can encounter God even in these most challenging moments. And we know that to be true of our human experience.

Dovid Bashevkin: You know, a lot of times people, they delay religious journey, religious growth till everything clears away, their schedule is open, they find total clarity, they want the heavens to part. And there’s something very beautiful about the fact that this first entry into the Holy of Holies, the first time he goes in, it’s in a cloud of smoke. You can’t even see much. It’s confusing, it’s clouded, it’s befuddling, you don’t really see the path right away, but you’re there.

Yaakov Glasser: And he knows and he knows God is there, and he’s experiencing God being there, and that’s like one of the climactic moments of the service. And we had all these hostages who came back. I’ve heard some of the interviews you’ve done, and people who have lost children, of hostages, you know, who came back, of parents of these people, and we have to be realistic. I don’t know that it’s true about every single person, but the number of people who discovered faith in a space where one would imagine is so devoid of feeling an overt—

Dovid Bashevkin: Clouds on clouds on clouds.

Yaakov Glasser: You can’t see anything. —it is just remarkable. Remarkable. And how is that empowering for us? It’s empowering for us because we shouldn’t view our struggles in life in opposition to our aspirations.

We should lean in and recognize that they actually contain a lot of potential for our aspirations.

In certain ways, it’s harder to find religious meaning when things are easier.

Dovid Bashevkin: Yeah. In certain ways, we create a lot for our kids.

Yaakov Glasser: We try to kind of like deflect—

Dovid Bashevkin: Yeah.

Yaakov Glasser: —as many challenges as possible, make it as easy as possible. Then we watch their Judaism, and first of all, inevitably they will encounter challenges. And second of all, we try all day to deflect challenges, even though we know all of our greatest strengths are a product of things that went wrong.

We know that!

Dovid Bashevkin: It’s, my whole life is that.

Yaakov Glasser: But we don’t have it in us, certainly not to introduce challenges, and we don’t have it within us to even allow them to happen if we could prevent them because we love them so much. But we have to know that once in a while, when they take hold, back off. It’s okay.

Dovid Bashevkin: There’s something to be found. there. Ba’anan eira’eh. You can discover something through the cloud, within the cloud.

Yaakov Glasser: And the imagery of clouds is all over, in Matan Torah, in the giving of the Torah, in their encounter with the mountain. This notion that, like, we can find God in these in these spaces is incredibly important. I’m trying to help people connect their real life. It’s easy to connect the things that are going well.

They’re on the side of the column of, okay, like, you know, “I’m rocking.” Good for you, so that side of the scale is solid. But what do you do with all the baggage that you bring into this? And it’s striking how Yom Kippur, which is a day of such accentuated sanctity, actually creates so much space for that baggage, so much. And to be able to unpack it, and confront it, and find greatness in it. And, you know, for me it’s actually embodied in the way it’s described, ve’inisem es nafshoseichem.

It’s actually a day of struggle, but it’s a day of struggle where it’s not just Hashem wants us to suffer, it’s He wants us to focus, and He wants us to see that we can find this.

Dovid Bashevkin: After the second immersion, we do a third immersion, and this is when the Kohen Gadol does the Mussaf that’s for like regular like as if it’s a Yontif. He brings the afternoon daily sacrifice that’s brought every afternoon. That’s immersion number three.

Immersion number four, which always intrigued me, he goes back in, but this time he’s not bringing something into the Holy of Holies, he’s taking something out. And he brings back that spoon and little plate, little saucer where the ketores were, and he brings it out of the Holy of Holies. Then the final, fifth immersion is he goes in, and then he kind of like finishes up the day, lights the menorah, and finishes up the day, and that’s basically the end of the service. The way Tractate Yoma ends, and it’s always profound, and it’s there’s a song about it, which is why a lot of people may remember it, is a statement by Rebbi Akiva, which is sometimes like hard to understand what he’s saying.

What Rebbi Akiva says at the end of Yoma, he says, “Lifnei mi atem mitaharim? Before whom are you purifying? Lifnei Avinu shebashamayim, your Father in Heaven. Mah hamikvah metaher es Yisroel, just as a mikvah can purify the Jewish people, so too God can purify you.” It’s a strange statement. I’m not sure what he’s getting at and why this is the closing mishna of all of Yoma. How do you find meaning in what Rebbi Akiva’s transmitting?

Yaakov Glasser: The meaning that I find in Rebbi Akiva’s statement, which is profound and discussed by many: you beautifully have been framing our journey through the avodah through noting the immersions.

Normally, when we immerse in a mikvah, it’s because there’s some sort of impurity that we’re trying to purify. Obviously, this High Priest, he spent seven days preparing for this. Part of those seven days is to remove any possibility that he actually contracted some sort of impurity. And certainly after the first time he immersed, doesn’t need to immerse again, and again.

So, obviously, these immersions are not about the transactional shift from impurity to purity.

Dovid Bashevkin: Because he didn’t get impure.

Yaakov Glasser: What’s he constantly going back to the mikvah? Like, why is he going to the mikvah? Over and over and over. And the Rambam, Maimonides, again, through the analysis of a lot of later commentaries, you know, notes that these immersions are not just about the shift from impurity to purity, but they are a form of emphasis of intentionality that’s layered into the avodah process.

And the reason for that is because a mikvah is a space where, beautifully developed by Rabbi Aryeh Kaplan, where a number of things happen in these immersions. Number one, it’s a space where you kind of return to your source of creation. Water is the foundation of creation. It also requires a descension in order to come up.

It requires a kind of an encounter with what it means to go down in order to come up. And it’s a chance to begin again. That is constantly layered into the Kohen Gadol’s experience. And I think what Rebbi Akiva is picking up on, and Rav Soloveitchik discusses this, is that we go through this entire process of watching this extraordinary service of the Temple, and we begin to imagine that our ability to reclaim our relationship with God, with our goals in life and with Judaism, is contingent on this process, on this Temple-centric process.

And for much of Jewish history, we don’t have a Temple. And we don’t have an ability to watch a Kohen Gadol. We could do it in our imagination and through the davening and through the learning about it, and in that way, we can recreate it, you know, but experientially we don’t have any of this. So Rav Soloveitchik writes that this statement that Rebbi Akiva made, that the mikvah could be metaher, the mikvah could purify, that God purifies the way the mikvah purifies, was actually stated after the destruction of the Temple.

Rebbi Akiva is known as this eternal optimist, this—

Dovid Bashevkin: transitional figure—

Yaakov Glasser: yeah, who can look at a space of destruction, which I’m sure will be discussed when you focus on the Tractate of Makkos, also at the end, where Rebbi Akiva sees this space of desolation and decimation, and the site of the destruction of the Temple, and he begins to laugh. And the reason he begins to laugh is because it’s a laughter of hope. And he’s able to conjure that laughter of hope because in the embers of destruction, Rabbi Akiva is able to see the capacity for light and illumination of redemption and reconstruction. And Rabbi Akiva is the one that kind of takes us through Jewish history and gives us that hug from the era of the Temple that even without a Temple, there’s a Temple within.

There’s a capacity within you to be able to connect to everything that’s brought to the Jewish people. And so, Yoma ends with this because, you know, Yoma means the day. Yoma is about Yom Kippur, and if you if you learn through this whole masechta, you’re going to discover very little of it is about our contemporary experience of Yom Kippur. Only the last chapter, really, is about our contemporary experience of Yom Kippur.

So, you could get very depressed learning this masechta and say to—

Dovid Bashevkin: yourself, “Yeah, like, ‘I don’t get a Yom Kippur.'” Right.

Yaakov Glasser: “Where’s my Yoma? Like, all I get to do is fast? Like, what is that?” What Rabbi Akiva is saying is that, you know, at the end of the day, the ability to return, the ability to purify, the ability to live in a post-destruction world where you can still search for redemption even in the challenge and in the destruction, that carries, and that outlasts even this moment, even this world of Yom Kippur. And that’s how he sends us off from Yoma, which, for me, is what we’re trying to accomplish here: extrapolate not just the formal technical things that happened—

Dovid Bashevkin: “Yeah, what happened, yeah.”—

Yaakov Glasser: —because we don’t have this today. We can’t watch what happened, but what we can do is relate to it, internalize it, live it, and then bring the totality of ourselves into this world of mikvah or into this world of transformation, and also be worthy of God’s forgiveness, atonement, and that’s what Rabbi Akiva is telling us.

Dovid Bashevkin: We always end our interviews with a questionnaire about your relationship with the Talmud, and I’m going to go really fast. My first question: Who do you consider your primary teacher of Talmud, and what did they teach you?

Yaakov Glasser: Two teachers taught me Talmud. One is Rabbi Yehuda Parnes, who is my first rebbe at YU. He helped me really become much more incremental and thoughtful, take it step-by-step.

Don’t just extract a point or a concept before you get to the conceptualization. Know the text. He was amazing. And the other rebbe was Rabbi Michael Rosensweig, whose shiur I was in for a few years, who really taught me how to creatively conceptualize things, and I would attribute a lot of this to him.

I wouldn’t blame, you know, he’s not responsible for anything I said. He has an amazing sefer of work. MiMenei Michael—

Dovid Bashevkin: former 18Forty guest. You should definitely check that out.

I want to mention that our fathers both had the same rebbe.

Yaakov Glasser: Yes.

Dovid Bashevkin: And I think that plays a role in our connection, and that was Rabbi Besdin, both our parents learned in JSS in YU, and the statement, I didn’t even know it was coming from Rabbi Besdin, but I would hear my father say it, and you heard your father say it, was said, “Stop talking about it, and let’s learn it.” A lot of people like talking about Torah learning, about Jewish life. Let’s stop doing about it, and let’s enter it.

Yaakov Glasser: Yeah, my brother is named for Rabbi Besdin, and my father quoted that often. And you know, I have to say that when it came to my own life, in my own development, he was always, and has been always, extraordinarily supportive not just of career development, but of the stages in my life where I was just learning more. I just wanted to learn and learn and learn and learn. And even though that’s not where he came from, he always supported it because he saw that was the substance from—

Dovid Bashevkin: which, ultimately Exactly, Jewish lives are built.

How would you explain to somebody who does not have a background in Talmud—you do have a background in Jewish outreach, so it must be that you’ve done this before—you’re explaining Talmud to somebody for the first time, how do you explain what it is and where would you begin?

Yaakov Glasser: I think that if you’re trying to convince them to do it by, you know, misrepresenting what it—like, it won’t you won’t get very far. You are stepping into the middle of a multigenerational conversation about the application of principles and texts to real life, to their real life.

Dovid Bashevkin: And I love that you said you’re stepping into the middle of a conversation, because there’s a lot that comes after the Talmud, that’s a part of the Talmudic conversation, and there’s a lot that came before. But you’re in this, like, sweet spot in the middle.

Yaakov Glasser: Yes. I mean, so many times I’ve started learning Talmud with somebody, and none of the masechtos—people are going to see this, so not like we have to hide this from them—none of them start at the beginning of anything. Like, the introduction situation is just like, what is the goal of that? And I think the goal is to experience it as a conversation so that you could see your own contribution to the conversation as a living part of this reality. Ask, wonder, what’s going on? In terms of where to start, I’m going to give you an answer that I don’t know is agreed by all.

There used to be an amazing rosh yeshiva that lived across the street from me named Rabbi Shlomo Singer. He was the rosh yeshiva of a yeshiva in Passaic called PTI, massive talmid chacham, and a mekariv for generations, and one of the original students of Rabbi Aharon Kotler, Rabbi Aaron Kotler. In fact, the set of books that we have from Rabbi Kotler, called Mishnas Rav Aharon, sure, is written off of recordings that he made with Rabbi Kotler’s son, Reb Shneur Kotler, which at the time required a machine so big that Reb Kotler didn’t want it in the classroom, cuz it was massive.

Dovid Bashevkin: Yeah.

Yaakov Glasser: So the two of them put it in the floor beneath and drilled a hole, he told me, in the floor so that they could put the microphone in there in the shiur room and the recordings could be made downstairs. That’s fascinating. And it is from those reels that he told me that they made these things. He told me that he had a tradition, I think it might have been from Reb Yaakov Kamenetsky, he did not introduce people to Talmud through the more practical aspects topically.

You know, you would think that like you want to get someone into Talmud so start them with what’s about—

Dovid Bashevkin: daily—

Yaakov Glasser: life, yeah, popular issues, talk to them with holiday, a shorter masechta, maybe Megillah, he jumped right in to the intricate tort law, damage law, complicated, stuff like Bava…, yes, he would start with Bava Metzia, and not only that, but he would start them off, he wouldn’t like layer in let’s first master how to read Talmud, and then let’s master how to read Rashi. Just throw them in the middle. Yeah, he used to attend shiurim of Rabbi Meir Stern, who’s the rosh yeshiva of Yeshiva Gedolah of Passaic, and he would find some way to translate this to a way that could be appreciated and understood by people with no background. And I’ll tell you a rabbi who I know does this, he’s in La Jolla, California, his name is Rabbi Daniel Reich.

He’s the rabbi of a community that has many people, thank God, that come from different backgrounds. Wish we all had more people from different backgrounds, and he made a conscious choice, a conscious decision not to just teach them introductory material from the Talmud and inspirational material from the Talmud, he teaches them lamdus. He does it carefully, he does it conceptual analysis, yeah, conceptually, he spreads it out, he explains the background. I think one of the places I would start with Talmud, first of all assuming you have a teacher, someone can guide you through this, is you know, jump in and appreciate the complexity of this, and some of the absurdity of this.

If you’re jumping in to when do we read the Megillah, so basically at the origin story of your practical halachic life, you want to skip—

Dovid Bashevkin: to the end kind of in a way, yeah.

Yaakov Glasser: You know, and you’re going to find it repetitive cuz the Talmud says it, and then the Tur says it, and then the Rambam says it, and then the Rama says, the Tur says, you know, and then you’re just going to feel like—

Dovid Bashevkin: yeah, you’re just going to read the weekly bulletin in shul.

Yaakov Glasser: You jump in to two guys are fighting over a tallis, and you’re like, why don’t they just stop fighting? You know what I mean? And then you realize that there’s been more literature written over thousands of years on the conceptual underpinnings of this contrived situation, of how to deal with this situation that then is applicable to countless practical situations in life. You know, to me, if you jump in to the more you know meaty, substantive components of it and build out, I think you’ll actually find yourself amazed.

Dovid Bashevkin: I absolutely love that answer. Do you have a favorite tractate?

Yaakov Glasser: Now it’s Yoma, I think so.

Dovid Bashevkin: It must be, right?

Yaakov Glasser: I think so, yeah.

Dovid Bashevkin: And it’s not just this camera, like you’ve been falling in love with it, you know?

Yaakov Glasser: Yeah, I think so.

Dovid Bashevkin: I’m so happy that’s your answer. I feel like we get an extra point when we interview the person for their actual favorite masechta. I think this is the first time that we actually got it, which is fantastic. Do you have a favorite story in the Talmud, and why?

Yaakov Glasser: Honestly, that story we were telling about Rabbi Akiva at the end of Makkos has to be one of my favorite stories, and I only say that because if you were to look through my Dropbox of source books that I’ve written over 20 years, you’ll probably find it in hundreds of…

Dovid Bashevkin: In every… yeah.

Yaakov Glasser: But also the story in Berachos where the leadership changed of the Jewish people, and they shifted the admissions policy of the academy, this—

Dovid Bashevkin: is Ben Azzai, Yehoshua, and Rabban Gamliel?

Yaakov Glasser: Yeah, from being only for the elite to kind of opening it up to everyone.

Dovid Bashevkin: Yeah, I really appreciate that. Do you have a favorite legal topic, a favorite sugya in the Talmud to study?

Yaakov Glasser: I know this is going to be a funny answer. I think the first tractate that I studied very seriously was Gittin, and one of my rabbeim gave me a project to memorize one of the chapters.

Dovid Bashevkin: Which chapter of Gittin, do you know?

Yaakov Glasser: The third.

Dovid Bashevkin: Really?

Yaakov Glasser: And it was like a challenge for like a teenager. I was 16 years old when I…

Dovid Bashevkin: Sure. Now, this is how you get teenagers pumped, you give them some—

Yaakov Glasser: yeah, ridiculous, whatever, and in fairness, this was before smartphones, you know.

Dovid Bashevkin: Yeah. Do you remember when you first fell in love with studying Gemara?

Yaakov Glasser: When did I first fall in love with studying Gemara? It probably was in my time in Israel. First of all, I was able to do it without tests and academic expectations, even though I have to say, my high school did provide opportunities to experience learning that way, but I don’t think I connected to it the same way still. But I think when I got the opportunity to kind of just slow down and experience it that way, over the years as I heard new people and new perspectives, you know, just renewed and reinvigorated. I have a funny relationship with Gemara.

Sometimes when I’m preparing for a shiur, I’m not in love, I’m frustrated. I feel like I need to get this. We shouldn’t over… over-romanticize every moment of Talmud study.

There are moments where you want to put your head through a wall, you know, and there are moments where you’re like this just there’s no way this makes sense. You know, like, I know for thousands of years they’ve been reading this page, but like I’m telling you, Well, like, I think it doesn’t click, yeah. they missed this, the Rashbam. But then of course, eventually you get help and you get clarity.

But like love with people, not every moment is a—

Dovid Bashevkin: Exactly.

Yaakov Glasser: is a honeymoon, and love with Talmud is the same way. Not every moment is a honeymoon, and that’s okay. There can be points of frustration.

Dovid Bashevkin: Do you have a favorite person in the Talmud?

Yaakov Glasser: I like when the Talmud calls the rabbis by their first name, you know, like, Abaye. Abaye and Rava.

Dovid Bashevkin: First name, yeah.

Yaakov Glasser: Like, this like sense that, like, we’re in the beis medrash. It’s weird, right? Like, how come we don’t have to—

Dovid Bashevkin: No, it’s very correct.

Yaakov Glasser: speak about them in third person or fifth person, the way—

Dovid Bashevkin: we do about all the other rabbis? And it’s much more common for the rabbis of the Gemara than the rabbis of the Mishna that we that—

Yaakov Glasser: Yeah. those honorifics disappear, and you call them like nicknames. It’s like a casual—

Dovid Bashevkin: Yeah.

Yaakov Glasser: So, I don’t know if there’s a specific person, but I find it fascinating how we relate to the people.

Dovid Bashevkin: I love that. My final question: Where is your favorite place and time to study Gemara?

Yaakov Glasser: Great question. Favorite time is Friday night, after the meal. Calmer.

Dovid Bashevkin: Quieter, yeah. Rabbi Glasser, I feel obligated to say this ’cause it’s one of the sweetest things I ever heard from you. I think one thing that you and I both share, since we’ve known each other, is a genuine longing for, like, the beis medrash environment and just being able to sit and learn uninterrupted, which happens less and less now.

And you told me one thing once that I always think about. I don’t know if you ever actually did it.

Yaakov Glasser: That’s 100%.

Dovid Bashevkin: But I love it, and I’ve done it a few times myself, which is to feel that you’re back in a beis medrash, and you’re sitting in your office, you would open up multiple tabs on your computer.

You want to explain?

Yaakov Glasser: So, I would go early to my office, and at the time I was learning on my own, and it was very quiet, very empty, it just didn’t feel like a beis medrash. I must have done it once by accident, and so I stumbled on it, and then I used to do it on purpose. I would open like 15 tabs on my browser of YUTorah, without any regard for what the shiurim, and let them all play at once. And I’m telling you, if you do this, and you crank up the volume, you will see it sounds like a beis medrash.

It is a kol Torah of a beis medrash, and I was able to concentrate better—

Dovid Bashevkin: Yeah.

Yaakov Glasser: you know. Like, I just Yeah. To hear all these tenuos going at once. Yeah. I have to say, as I’ve gotten older, probably the opposite. Like, I don’t know if that’s an age thing—

Dovid Bashevkin: Yeah, you need a little bit more.

Yaakov Glasser: but now, yeah, now like it’s like—

Dovid Bashevkin: You hear like one car go by, you’re like, yeah, exactly. if there’s a gardener outside, like, oh, I can’t focus. Rabbi Glasser, for our friendship, for your mentorship, for all the years, really, you were my you were my first boss, and I feel like so much of who I am today was shaped through your influence and your direction. Thank you so much for joining us today for Talmud Daily.

Yaakov Glasser: I appreciate it, and I appreciate you, all of your different venues, especially this effort to bring the Jewish people towards the Talmud.

Dovid Bashevkin: Thank you so much.