An Interview With Rabbi Gershon Winkler

Rabbi Gershon Winkler may be known to many of our readers as the author of The Golem, The Dybbuk, and The Maiden of Ludomir. But this former kiruv rav is also the author of Travels with the Evil Inclination, which chronicles his journey from the study halls of Borough Park to the wilderness of the rural west. A widely recognized scholar of Jewish theology and mysticism, Rabbi Winkler is the founder and Executive Director of Walking Stick Foundation, a non-profit organization devoted to the recovery of aboriginal Judaism.

I met Rabbi Winkler during his most recent stop on the East Coast. He was different in person than I imagined. For someone whose writings radiate larger-than-life courage and ballsyness, I expected a giant, swaggering man.

Rabbi Winkler does not swagger. He met me wearing a red t-shirt and dark sweatpants, his bald head bare. If you put him in a black hat and a dark suit he could easily be the sweet rebbe you always wished you had or a jovial, mild-mannered Santa Claus. He used dramatic voices and a constant gentle chuckle as he shared Torah stories and teachings that flowed as naturally as his breath. Gesturing with his hands as he spoke, his eyes sparkling, he constantly quoted rabbinic and Talmudic texts, giving a view into his mind where these ancient worlds and teachings and characters seem as real to him as if they existed right here beside us.

This interview explores the path of an elder compatriot, who, while living a life steeped in Torah, is simultaneously an “Unpious” star. –Leah Vincent

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Leah Vincent (Unpious): When you left the religious community there wasn’t any kind of support system, was there?

Gershon Winkler: No, I had to leave the entire state of New York altogether, had to go to the wilderness.

Unpious: Did you know others, did you connect with other people who were leaving?

GW: Not for a long time. It was just my own stuff and I took off into the midbar.

Unpious: So, let’s go back a little earlier – I think it was your last children’s novel, The Maiden of Ludomor –

GW: I wrote that during the transition period. I had already left when I wrote that one.

Unpious: But it was published by a religious publisher, right?

GW: Yeah, by Jack Goldman, alav hasholom, at Judaica Press, by Otzer Hasforim. He even had it read by Rabbi Dovid Feinstein, Rabbi Moshe Feinstein’s son, to make sure it was kosher. Reb Dovid read it and said, “It’s a great book.”

There’s a whole difference between the old school of rabbanim and the more fundamentalist new school. They got stricter and stricter. So the older people, they loved it. My mother loved it. She had a hard time getting it, though. She went to Eichlers in Flatbush and asked for it. They said, “Oh, we don’t sell that.” Then she walked away and the guy said, “Are you sure you want it?” She said, “Yes.” So he reached down behind the counter and brought up a copy.

It was already banned by the Agudas Yisroel during their Thanksgiving weekend convention, for encouraging Bais Yaakov girls to – I didn’t encourage anything! I just told a story — for encouraging them to, God forbid, seek out more learning or become great teachers beyond the seminary walls. We had many great women in our tradition, we just don’t talk about them. Especially with the problem that most of them had, which was that she [Chanah Rochel Webermacher] didn’t want to get married and have children. That was a terrible thing. If she’d get married and have children, then we could put her among the great heroines of our people. She could be under the thumb of her husband and in his zechus she’d be known.

Unpious: Were you trying to push the envelope when you wrote The Maiden?

GW: I was trying to, while not trying to. [Laughs.] There’s a little bit of me in there, in the dialogues, that I took out of actual sources in the Aruch Hashulchan and other seforim that are more lenient about women studying gemara and things like that, so I just inserted those things into her conversations. There was me in there trying to share with women what I felt they deserved to know.

That’s how I got in trouble to begin with. I got kicked out of teaching at a yeshiva in Brooklyn. I was teaching at Dvar Yesharim and another place, I forget, two ba’alei tshuva yeshivas. The problem was, I began teaching not just the party-line view of halacha, I’d also give other opinions: “However, there’s another opinion in the Rambam that says it is allowed and this and that.” So they said, “You shouldn’t be teaching that.” I said, “Why? The Rambam says it’s allowed, why shouldn’t they know and make choices?” “They might take advantage and do it the easy way.” Ah!

I believe if I’m going to teach Torah I’m going to teach shiv’im panim, the whole gamut. If you look at our Shulchan Aruch it doesn’t just have the halacha. It has a thousand little rabbis crawling through the pages, hiding behind brackets and parenthesis saying, “However… not quite this way,” or “It depends on the context,” and things like that. So that’s what I began teaching more and more, because people were asking me questions. “Does that mean I have to wait fourteen days, a full two weeks, before I can be with my wife?” “Well actually in the Torah it’s seven days, and anything short of intercourse isn’t such a terrible thing midoraysa, only miderabanan.” Stuff like that. It got me into a lot of trouble. [Laughs.] “You have to get married to have sex?” “Well you don’t really have to get married according to the Ramban, he says there’s a tshuva and according to this rabbi and that rabbi and the Talmud itself says there’s marriage and there’s non-marriage…”

So they were nice to me, they gave me an option: “Either teach the way we do it or leave.” So I thought about it for a very, very long minute and then I left.

Unpious: You were married then, with children?

GW: Yes, I was married with children, to a nice frum wife, very very frum, more frum than Moshe Rabainu. She covered everything, I hardly knew what she looked like. It was very hard for me, because the more I began to look for more lenient sources to share with my students, the more the yetzer hara began to get to me, and so the yetzer hara and I became good friends and we hung out for a while. Little by little, I influenced him a little bit, he influenced me a little bit, that’s what happens in friendship. [Laughs.]

In the end, the good lady said she couldn’t live with me the way I was and I realized I couldn’t live there altogether, so we parted as friends.

It took us a few years to do the get, because the rabbanim, our great sages, kept telling her that I’m probably going through a phase. “Gershon Winkler, of course he’s going through a phase. He’ll come back to the real emesidike derech.” Do you remember terms like that?

Unpious: Oh, yes!

GW: Good, we don’t want you to have lost it altogether. [Laughs.]

Unpious: No, I’ve got huge pieces of my brain filled with totally useless information like that.

GW: [Laughs.] So we did a nice get, together with some rebbe in Borough Park. We had lunch afterwards at a dairy restaurant on 13^th Avenue, and that was that. She remarried a really nice guy.

Unpious: Did you get custody of the kids? Any type of visitation?

GW: Yeah, we worked it out between us. There were no bad feelings. I would come in from West Virginia, where I lived in the woods, and we’d spend a week or a weekend, and she’d go someplace else. I did this twice a month. I’d be there for, like, five days each time, sometimes for Shabbos. The kids would rush me in to the house, they didn’t want other people to see a guy in a plaid shirt and jeans. “Abba, please, please get in the house.” [Laughs.] I’m still very close to my children and grandchildren. When I visit them I become very frum. I shuckel when I talk, like I do now [gestures]. I’m practicing because I’m on the east coast. I wear a very big yarmulke, it covers my whole body. It’s motorized, I drive around in it a little bit. [Laughs.]

Unpious: These days, when people decide they have to leave their families because of these reasons, the community gets together and does everything it can to prevent them from having a relationship with their children.

GW: That’s terrible. It’s like these cults that they talk about.

Unpious: I think you are right, things have really changed a lot between the old guard and the new guard.

GW: It is very true. My father is very old guard and he used to walk around Lakewood, back when my mother was alive, hand in hand with her, even though it was not something you did. A long white beard and a big sheitel – not him but her — and it was such a different feeling. My rebbeim, when I was in yeshiva, were the old guys, hundreds of years old, from Russia and Poland, and other places. They were very open-minded and open-hearted, even though they were very rigid in their own practice. They knew there were other opinions in the world.

I remember Jack Goldman at Otzer Haseforim, one of the last projects he wanted me to work on, before The Maiden, while I was still kosher, was a translation of the responsa of Rabbi Moshe Feinstein. So I started working on it, and all of a sudden he gets a call from Rabbi Moshe Tendler, of the next generation. He says, “It is strictly forbidden to put this in translation because there are many opinions that people can misconstrue.” Feinstein, of course, was very lenient. He annulled marriages left and right instead of letting people become agunas. Regarding Cholov Yisroel, he says, “I strictly abide by it but there’s no reason for it anymore. We no longer mix milk from different animals, it’s supervised by the government,” and all that stuff. “You don’t have to dress a certain way, it’s not like chukkas hagoyim.” He has many such responses. So I was stopped, lest it be read by too many people. God forbid that a nice observant Jew should see that there is flexibility in halacha.

Halacha literally means walking. Hilucha. It doesn’t mean law. If I’m walking and there’s a wall in front of me, what am I supposed to do? [Laughs.] The halacha flexes. What you do – what’s that guy’s name with the purple crayon?

Unpious: Harold*.

GW: Harold. Yes, you do what Harold does. [Laughs.] You take up the crayon, you draw a door and you open it, and you move through it. You know, people couldn’t do Pesach in the desert because they were busy burying the dead. So that’s it? They had to miss Pesach? No! Pesach Sheni!

The farther back you go, the more flexible it was. Now there’s such rigidity. I never knew it in my time either. These days women are clad in darkness. They used to walk around in colorful clothing on Shabbos. Now it’s all dark and black. “You can’t do this,” “You cant do that.” It’s a rigidity that makes a person feels very special. You know, “We’re very different. The world is becoming more lenient therefore we have to become stricter. Ah, we’re doing something good, very good.”

But in the process it strangles the neshama. You can see it on people’s faces. When I walk through Borough Park or Flatbush or Lakewood, you see it on the women’s faces. One woman and a hundred thousand children. In the old days, you had four women and three children. [Laughs.] “Everybody have as many kids as you can squeeze out of your poor hapless body.” “It’s ok, it’s for Hashem.” And Hashem is going: “Oy myself, oy myself! I can’t believe they’re doing this in my name.” Aim kol chaya l’chayim nitna  — the Talmud says she was given for life, through aliveness.

You see it on the men too. They carry such burdens: “Oy, I’ve got to say Tehilim.” “Oy, it’s almost time for mincha.” This is not what the chachamim intended. They didn’t have seforim back then! [Laughs.]

Unpious: Your life is still devoted to Judaism of a very different form. How have you determined for yourself what is what you call “aboriginal Judaism” or authentic Judaism and what is crap?

GW: I’m still figuring it out. There is so much crap that evolved over the millennia. Fences around fences around fences that we have forgotten what we were building a fence around to protect. There’s a whole teaching about it in Avos d’Rabbi Nosson. In the very beginning it says, “Be careful, chachamim, that you do not build a fence so high that it might fall and crush the flowers you’re trying to protect.” That’s what happened over the centuries. We’ve gotten so insulated. Part of it probably from the trauma of hundreds of years of oppression and part of it because we lost touch with our origins.

You read the mishna and you see how people used to bow to the four directions – the mishna in Shekalim — four times to the north, three times to the east, four to the south, two to the west. There was an honoring of the winds. The omer is another example. Today they ask, “Murmur, murmer, did you count the omer?” If you forgot to count the omer you have to say it today without a bracha and do it with a shinuy and maybe you should have a yarmulke on the back of your head. What was the omer? The mishna says they took the barley every day and they would wave it front and back and towards the sky and the earth as a prayer for warding off bad winds and bad rains because they were concerned about the crops.

So there’s a lot of aboriginal in the mindset of ancient Judaism. But then we got thrown off the land, we got put into situations where we had to find work that had nothing to do with the land, with nature, with creation, so slowly but surely we slip-slided away. They just remained things in books, but not in real life, not in real contact with trees. “Trees talk to one another,” the gemara says. There are a lot of things like that.

I find all this richness in our tradition and I see so many of our people going to Peru or other places because they’re thirsty. It’s in their blood. They want to connect with the reality of creation, with the world that they live in, with the planet. So I try to recover some of these teachings to share with them, and say, “Hey – you don’t have to leave your Peruvian shaman, but just want you to know, we got it too.” [Laughs.]

Unpious: Do you think that whatever authentic Judaism is, it has some truth about what you call the reality of creation?

GW: Yeah, I really do. The Torah itself, she begins with it. She doesn’t begin with Jews. She begins with a non-Jewish God, a goyish God. No Jews around, the creation of planets and the sun and the moons. Why is my yiddishe Torah telling me about the sun the moon, the planets, water high and water low, trees, animals – what a waste! All those six days – finally we get to a person! And he’s not even Jewish! Adam and Chava, not even Jewish, they give birth to non-Jewish people. So many non-Jews, going on and on as I continue reading Bereishis. Chanoch, he’s not Jewish either and he goes up alive to the heavens! A goy goes up to the heavens! No Jews yet. Why am I going to shul to listen to the parsha?! I’ll wait until I get to Avraham Avinu after he circumcises himself, before then I don’t want to hear about it. His name was “Avram,” not such a Jewish name.

The way the Torah is organized it’s so conspicuously calling out: before you can be a good yid you have to be a good human being, you have to be a good goy first and before you can be a good goy you have to be a good animal and before that you have to be a good tree, a good rock, a good planet.

You see all these connections and you come to the halachos later. After you become nice yiddishe people in the desert, wandering around looking for Tel Aviv, we’re told that when we get to the land we can’t own it or work it on the seventh year, the fiftieth year, we have to leave it alone because nobody can really own the land. We can’t sell the land. “It’s not yours.” Ki li kol ha’arretz ve’atem toshavim. The Torah is very much picking on connection with the land, that’s part of the religion. The spiritual practice has to do with the earth. The Chag Habikkurim coming up, on Shavuos, it’s not called Shavous, it’s Chag Habikkurim – the festival of the first fruits. Pesach, the first harvest, Chag Hakatzir, and Sukkos is called Chag Ha’assif. Everything is interconnected.

Unpious: Some of our readers, coming from this world that has a lot of nonsense, are seeking truth and they find science and they think, wow – finally someone’s speaking truth to me. Do you think there’s a place for the kind of Judaism that you’re talking about, that’s more about spirit and emotion and origins? What might you say to them about how to reconcile their desire for something that’s really logical and rational but also allowing a place for spirit and emotion?

GW: Yeah, there’s place for that too -  it’s room number sixty four, because in room number sixty four there are teachings they don’t tell you in yeshiva, teachings likes those of Rabbi Yitzchak of Acco who lived in the thirteenth century, a disciple of the Rambam. In one of his works, Shoshan Yesod Olam, he writes that he estimates the age of the universe thirteen and a half billion years.

Unpious: They didn’t teach that back in Bais Yaakov!

GW: This was back in the thirteenth century! People say the world is five thousand years old. That’s not what we believe. The way Chazal put it, Adam and Chava were created five thousand or whatever years ago – not creation of the earth, not the universe! How can you say it means [literally] six days when the sun wasn’t even created until the fourth? We determine days by the sun and the moon. Obviously it’s talking about cycles.

Shamayim, the gemara says, is aish and mayim – fire and water. It’s very aboriginal, even in the way we created words. So for a person who’s studying science and saying, “Oh, this makes more sense,” there’s no contradiction. The Torah is not speaking about days any more than if a scientist tells you, “I’ll see you at sunset.” You can challenge that – “I thought you were a scientist – you really believe the sun sets?” No, it’s a manner of speaking. “Lo dibrah Torah ela lashon b’nai adam.” The Torah speaks in the language of the mortal. It speaks to us in the language of where we are. From our perspective, the sun looks like it’s going down. That doesn’t mean that’s what we believe. So yeah, you can always reconcile all these things -  just don’t tell your rebbe! [Laughs.]

Unpious: How do you differentiate what you’re talking about from the Conservative and Reform movements?

GW: Yeah, that’s a good question. I try not to think about these movements. [Laughs.] I try not to think of any movement at all, except for the bowel movement. That’s the only one I can relate to personally.

There are many good ideas in the world. The problem, in my opinion, is that once they became a movement, they stop moving.

The Reform movement, of course, didn’t start on the right foot. They wanted to throw everything away so they could be like everyone else. That, to me, is not a good intention for anything. You have to find a way to be more of who you are, not because you want to be like someone else. The cost of self-compromise is very great and it cost a lot. A lot of our people left because they were given a freeze-dried Judaism and no one offered them water and said, “Stir!” Then came the Conservative movement and added water and said, “Stir!”

That created the Orthodox, just by default. There was no such thing as Orthodox before the Reform movement. There were just Jews. Jews who did a little bit, Jews who did a lot. Jews who did a lot and a little bit. Jews who cheated, Jews who didn’t cheat. Good Jews, bad Jews. Even the Midrash — in Bamidbar Rabbah – says, “There are many Jews. There are Jews who observe the Torah, Jews who don’t observe the Torah, Jews who do gemilas chasadim but they don’t observe the Torah, Jews who observe the Torah but don’t do gemilas chasadim, but they all come together be’agudah achas and we become one people.” There are many of us.

So likewise here, when you establish a movement and say, “We are now becoming the Conservative movement,” in other words, “here are our guidelines,” you again create the very thing you ran away from – orthodoxy. Because orthodoxy is not only in frum – in frumology. Orthodoxy also appears in the Reform movement or the Reconstruction or Conservative or Polydoxy or Renewal. Any kind of movement that suddenly begins to determine the proper guidelines for those that want to become members and creates its own codification, its own code, becomes another version of Orthodoxy.

The problem is not how much we observe. The problem is orthodoxy. Because orthodoxy puts these blinders on our peripheral vision and the Torah, we’re told over and over and over again, in the gemara and the Midrashim, was given to us to remove the blinders, to take us out of slavery.

Chairus al haluchos, which means, engraved on the luchos. The Gemara says, chairus also means freedom. [Laughs.] So if you want to look at only “engraved,” that aspect of it, farfallen, you’re back in mtzrayim. If you’re going to remove the blinders, you’re going to allow yourself to see and receive the different ways in which the Torah speaks to us, then you’re there. Then you don’t have a movement. You just find your community or your people and you hang with them and if they don’t work anymore you go somewhere else. No dues attached.

That’s my problem with them. With all the movements. Look at what happened to the chasidish movement. The Baal Shem Tov, the Maggid of Mezerich. All these great stories, these rabbanim who were so fluid and flexible and told stories instead of davening mincha, and taking sick people out to trees in the woods and dancing around them with torches like wild Cherokee Indians! But once it became a movement it killed itself. If the Baal Shem Tov or the Maggid was alive today, they wouldn’t recognize Chasidim. They’d say, “Who are these people?” “What religion is that?” “Are they Cossacks?”

Unpious: Who are your role models in Jewish history for the life that you’ve chosen and the values that you teach?

GW: My heroes are Rabbi Akiva. Rambam. Bar Takonas – second century – he was a troublemaker from Pompadisa. Most of the teachers at the yeshiva of Pompadisa went against the grain, just for the pure hell of it. [Laughs.] When I read a story of the Baal Shem Tov, of Reb Levi Yitschak of Berdichev, it’s inspirational that these people existed. When I read the responsa of Reb Moshe Feinstein, he was a man who was thinking, thinking beyond the box. He wasn’t afraid.

My father, he was a great hero to me too. I remember [one Shabbos] when I was walking in Lakewood, visiting him. My daughter of my second marriage was very little, she was crying, she didn’t want to walk back to the hotel. My father was escorting us. He’s an old yid, an old rabbi, the last surviving disciple of the Chofetz Chaim. So he’s walking with us and I’m afraid to pick the kid up, because I don’t want to dishonor the custom. I don’t know what to do. My father says, “Pick her up, she’s crying!” “Is it allowed?” “She’s crying!” So I pick her up and people are giving us bad looks, but my father just keeps walking with us. He doesn’t walk ten feet behind like I’m not with them.

He’s always been a role model to me, and his father too, although I never met him. His father was a disciple of Reb Yosef Chaim Sonenfeld, who was the founder of Neturei Karta. [Laughs.] He left all that and went to Europe from Yerushalayim.  He went to university, got a PhD in the New Testament. [Laughs.] He became a rav in Hamburg and Frankfurt-on-the-Main and eventually in Denmark, in Copenhagen. He was one of the few rabbanim who supported Sarah Schnierer. When they had the Agudas Harabbanim meetings about her idea, of, God forbid, having a yeshiva for women, he was a very loud voice. He’s mentioned in many of the books about her: Rabbi Michoel Shalom Winkler.

Throughout the gemara you find so many interesting characters who bravely taught and lived in ways that were not mainstream. Like Abba Chelkiya, Choni Hamagil. All these fun guys. Akiva, who laughs when jackals are running across the Temple Mount. He was able to see beyond the churban to also see the nechama and the yeshua. Shimon bar Yochai and his crazy teachings that are mentioned in the Zohar and other places, wild teachings about how he meditated on the earth a lot and wept on the earth and thanked the earth after he finished meditating. So many people like that, whose teachings have inspired me, moved me, because they went beyond the box, they challenged me to look peripherally. The Ramban, who writes in his commentary on the Torah, “With all due respect to my elders and teachers, I am not a donkey obligated to carry their their views on my back for the rest of my life.” Ibn Daoud, the Rybid, who challenges the Rambam. The Me’iri, he was a great rabbi, a great teacher, also who saw things beyond. Yitschak al-Fasi, Yochanon ben Zakai, Hillel.

Yochanon ben Zakai: “No more shofar blowing when Rosh Hashana falls on Shabbos,” they told him. “Bais din has declared it for all of Israel.” So what does he do? He says “We’re blowing it all over Yavneh anyway.”  So they say to him, “But how can you defy the halacha as it has been ruled by the majority?” He says “We’ll talk about it afterwards.” The gemara then continues, after Rosh Hashana they approach him and say, “So — let’s talk about this.” He says “Why? It’s already been done!”. [Laughs.]

Unpious: The ultra-Orthodox community today has chosen to silence those voices of dissent.  In the context of our history, where do you think the ultra-Orthodox community will end up? Do you have a prediction?

GW: It’s like when you have a sack of flour and there’s a tear at the top, then you’re inclined to tighten the top. But when there’s a rip at the bottom, the more you tighten the top, the more you’re going to lose. I mean, you just told me that thousands of people are going to this site [Unpious.com], and I’ve gotten calls periodically, sporadically, throughout the years. There are people out there and know they’re there, and you see it on the faces of people. You go to the pizza shop in Borough Park, there are people who just can’t bring themselves to do anything about where they are, because it’s so ingrained in them, there is nowhere to go. So you go to the pizza shop at night, at one o’clock in the morning, and hang out with other demons, the demonic frummers. [Laughs.] You feel the shadows, the darkness, the heaviness. Nobody knows where they’re going, where they’re coming from, why they’re here, what they’re doing.

Thank God there are those who have enough spark left in their neshama that they believe in the capacity of their self, their essence, of the unique gift that they are in the world, that has nothing to do with how people judge them or define them, and then take the leap, take the chance.

So how do I see it in the future? What I see right now is that there’s an inverted Judaism, and it’s going to self-destruct. It’s leaking like crazy.

The hope is with those who either see this is happening and live beyond it, even within the frum community, and those who have left. Because in leaving and even in seeking other things, it will bring you far enough out that you can see back in a little more clearly. So I feel that there’s a freshness that will hopefully happen from that.

Unpious: Some of the people who leave feel strong anger and hatred towards Judaism. What would you say to someone like that, who feels anything Jewish — they just don’t want to hear about it. To them it’s just bad and evil and toxic.

GW: Yeah, that’s why I wrote the Shmelves. [Laughs.] That’s a very good question. When I meet a person like that, I tell them that I totally understand, because this was the context in which it was given to them. If somebody gave you a pizza that was laced with staples you would never eat pizza again, ever, or even look at something that had an Italian name on it. It doesn’t necessarily mean all pizzas are like that. It’s the same with people. Some people are good, some people are bad, and even though they’re people in the same family, there can be bad siblings in one family, it doesn’t mean the whole family is bad.

The gemara says, “Mibnai banav shel Haman limdu Torah be’bnai brak.” The descendants of Haman taught Torah in Bnai Brak. [Laughs.] It’s a reminder to us that yeah, we do have bad experiences in the world. The German people slaughtered us – but their grandchildren didn’t. This is our way, this is a very important way of living a more wholesome life, when you don’t reject the entire thing because that’s what they did to you. They pushed the entire context of everything on you and said you have to do all of this or you’re doing nothing at all. Here we’re doing the same thing. [Laughs.] “I can’t take any of it.” It’s the same idea, same stream. You should be better, you should grow even taller, and say, “You know what? This was a very bad experience, it was sad and sacrilegious in the way that my rich tradition was presented to me, because it wasn’t presented to me, it was clobbered over my head. And it was clobbered over my head with disrespect to my dignity as a human being and my capacity to think for myself.” Totally antithetical to everything that the Torah teaches.

I invite people to come to some of my events because these teachings have nothing to do with how many times you have to put on tefillin. It has to do with more kavanah towards the whole thing. What is the intent of this thing we call Judaism? What is the core? What does Torah mean?  Does it mean law? That’s how they translated it into Greek, but you’re not Greek, you’re Hebrew.  And in Hebrew, Torah means guide. “Leohorot,” to guide, to show. It’s a perfect story about imperfect people in imperfect circumstances with imperfect relationships with the Torah itself and with God who gave the Torah.

It’s a great philosophy that’s completely perplexing, which is why our philosophy book is called The Guide to the Perplexed. We don’t have a code of philosophy, because every time someone codified anything, somebody else would come and dispute it. It tells you something right there. It tells you that you do have the right to question and no one has the right to stop you. In fact there’s a gemara in Horayos where it says that a student who sits in front of the sanhedrin and hears the sanhedrin make a ruling that he disagrees with, and he says nothing, he has to offer a korban chataos, for not questioning. It’s a sin in Judaism not to question!

It’s important for people like this to understand, to know, that there’s a huge discrepancy between what they experienced and what they were taught and what is really there, and to give everything a fair trial. You’ve got to go look for yourself. Don’t listen to the way it was told to you. Read about Rami bar Timri who comes to the village of Rabbi Chisda and makes trouble there. He eats cow udders, which is forbidden according to Rabbi Chisda. Rabbi Chisda says, “How can you eat cow udders? It’s forbidden!” He says, “I’m from Pumpadisa. Rabbi Yehuda there allows it.” There are such openings. That’s why I wrote the book The Way of the Boundary Crosser. I put in all the sources, all the mar’ei mekomos for these kind of teachings, for rabble rousing, teachings that demonstrate over and over again how the talmidim always questioned and challenged their rebei’im, and how their rebei’im encouraged it, because that is Torah. Ailu v’ailu divrai elohim chayim.

And that’s been lost to us. Now it’s only “the way Rabbi Blumenkrantz says it,” or “Rabbi Miller says it,” or rabbi whoever. It has to be this way and this way only, otherwise I can’t daven with you. “You’re wearing a colorful tallis? Oy, you might be chayav skilah if you walk around with that. Has to be black and white only!” Where is it written? “I have no idea. It must be written somewhere because we all do it this way.”

Unpious: You’ve faced so many challenges but you have the most terrific sense of humor. You’re one of the funniest people I know. How do you maintain a sense of humor in the face of all the challenges and stay light instead of becoming bitter?

GW: I guess growing up reading and studying all this stuff – how could you not have a sense of humor? Our people were funny right out of mitzrayim. They said “Are there not enough cemeteries in Egypt you had to take us out here to die?” We were always funny. Humor is a very integral part of our heritage.

In Tehilim, perek bais, what does it say there? Yoshev bashamayim yischak. The one who sits in the heavens is laughing.

Two personalities who inspired my tendency to laugh at things, for seeing the lighter side of things: The first was Akiva – most of the stories about him are how everybody weeps and he laughs. [Chuckles.] He was able to look at other parts, which is very helpful for me.

I think it would be helpful to a lot of people to know, you’re walking in the dark but that doesn’t mean there’s no light on the other side of the earth. When its night here, it’s daytime in Australia, don’t forget that, and you belong in Australia as much as belong here. Same planet, same globe. And he, Akiva, always walked with one foot in the literal and one foot in the mystery. “I don’t know everything, I don’t know the end.”

Like the way I say brachos. I say, “Baruch ata I-don’t-know.” Who knows the [answer to the] great mystery?

The second personality was my mother, aleha hashalom, who passed away a few months ago. She died laughing. She was very funny all the time. The funniest person in the world. When she would tell a story people would fall off their seats and roll on the floor laughing, some near death. She was always very funny. She grew up very frum, and always remained very, very frum, but she always had this [sense of humor].

Perhaps it was because we came from a country where people were very lighthearted. She came from Denmark and people there have a very good sense of humor, everything is laughed at. When the Nazis took over, they laughed at the Nazis. They didn’t go to war with them — they had only a little army of two soldiers and half a gun. But whenever the tanks would go by people would just turn around. So they destroyed the [Nazi] morale. The Nazis would get on a bus, and all the Danes would get off. They’re just a very lighthearted people. That’s where my parents were My father, course, went to Russia to learn in yeshivas and everything. But my mother was very influential humor-wise. So I’d say Rabbi Akiva and my mother. [Laughs.]

*Harold and the Purple Crayon

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Tags: In Conversation, rabbi, Rabbi Akiva, Rabbi Gershon Winkler, rebel, scholar, Walking Stick Foundation, Zohar