He was a rebbi’s rebbi. That’s the description that long-time menahel, Rav Chanina Herzberg, used to describe, Rav Yaakov Pressman, who was a devoted 7th- and 8th-grade rebbi at Yeshiva of South Shore for nearly half a century.
His impact on every boy who walked into his class was profound. His talmidim now range from those who are roshei chaburah in Lakewood, mechanchim across the U.S., roshei yeshiva and maggidei shiur in Eretz Yisroel and of course the gamut of frum doctors, lawyers and every type of professional and worker. Despite their diverse paths, they all have one thing in common: they all loved and revered Rabbi Pressman who taught since 1972 at Yeshiva Toras Chaim of South Shore.
But he was not always a rebbi. Rabbi Pressman was an American boy from Providence, Rhode Island. In the late 1940s, when Yankel, known as Jerry, was about ten years old, there were no yeshivos in Providence. Rabbi Pressman’s mother, Ruth, left Providence, while her husband stayed behind for their parnossah, and she moved with her son, Jerry, to New York. She was moser nefesh so that he could learn in the Toras Emes Yeshiva elementary school in Boro Park. Like all American kids, especially those from Providence, gadlus was not on his mind. Football was. Young Yaakov had a picture of his favorite football player inside a special place in his wallet and he cherished it.
Meanwhile, his mother had gotten a job in New York for a very distinguished Jew who had escaped the Holocaust not long before and made it to America. His name is well-known to any person who has picked up the most revised edition of the Rambam – Reb Shabsi Frankel.
One day the Ponovezh Rov came to Reb Shabsi Frankel’s office to collect for his yeshiva. He met Mrs. Pressman, who told him her story and explained to him that her young son was learning in a yeshiva. The Ponovezh Rov was very impressed that in the 1940s there was a woman who came alone, from Providence to New York, just so that her son could go to a yeshiva. Somehow, he had a picture of himself (or perhaps there was one in the office), but he personalized it and autographed it with an inscription to Yaakov Pressman. He told Rabbi Pressman’s mother to give it to her son, Yaakov. And the moment Yaakov received it, his plans immediately changed. No longer did he want to be a football player, he wanted to become a rosh yeshiva. From Toras Emes he went to Torah Vodaas to Bais Medrash Elyon where he learned under gedolei Yisroel including my zaide, Rav Yaakov Kamenetzky.
He may not have become a rosh yeshiva, but in his classroom, he most certainly was. My father would call Rabbi Pressman’s class, Yeshivas Volozhin. He then put up a sign in the classroom, “Yeshivas Volozhin” together with pictures of gedolei Yisroel who were talmidim or the descendants of the talmidim of that revered yeshiva. In the center, the boys put up a picture of their rebbi with a Litvishe rabbanishe yarmulke. (I’m not sure how they got it.) He never took it down. If the boys enjoyed it, he did not mind. In fact, he said that could use it yearbook picture as well!
He taught at a very high level, especially toward the end of his career, when the yeshiva asked him to give an honors class to a select group of talmidim who were ready to meet an even higher standard.
One of the last years that he taught, I asked the rosh yeshiva, Rav Elya Brudny, to farher his class. Before he came in Rav Brudny, asked, “Where are the boys holding? What can I ask them?”
Rabbi Pressman said he would write out some ha’aros relating to what they learned. He handed Rav Brudny two pages filled with questions from a large array of sources. Rav Brudny was quite surprised. “This is what they learned? They will be able to answer these questions? You taught them this? They’re going to be able to answer questions on these Rishonim, on every Tosafos?”
After the farher, Rav Brudny was extremely impressed with this group of Long Island boys who, in his words, could stand up to any other boys their age across the city, that he had farhered. After the farher, he impressed upon the 13-year-olds, the inyan of connection to Har Sinai and how lucky they were, as there are hardly any other children in America their age whose rebbi was like Rav Yaakov Kamenetzky.
Indeed, in the last 5 years or so of his long teaching career, he had taught a smaller class of very motivated boys, but no matter the size, he did not compromise on the level of depth and clarity he transmitted. He began the day with Mesillas Yeshorim, in-depth, he learned Sefer Vayikra in-depth, going through every nuance of every korbon. Alumni who ended up in Brisk have told me that the tools for Kodshim that they needed, were given to them in eighth grade by Rabbi Pressman. He learned Bava Kamma, but every year a different perek, from the first to the last he would plow through a new perek each year preparing with his dear (but younger) chaver from Yeshiva Torah Vodaas high school and bais medrash, Rav Moshe Scharchon. He wanted every year to be a fresh limud, something he had not taught in ten years.
He would tell Rabbi Scharchon, “Think of any question that could come to the mind of an eighth-grader and ask it to me. This way I can prepare a response for the most left-field question a child may ask.”
When they were first hired in the 1970s neither Rabbi Scharchon nor Rabbi Pressman owned a car. They traveled together by train, taking a subway to the Atlantic Avenue Station and a Long Island Railroad from there. “Rabbi Pressman taught me how a Yid is supposed to ride on a subway,” said Rabbi Scharchon.
He taught up to the boys. During the days following his passing, I received many texts and calls relating stories and life lessons that rebbi taught. One of them told me, “Rebbi taught us about making a sefer of cheshbon hanefesh.” He had a book in which he would go over his day and the children emulated him because they revered him. He was so real to them.
Despite the disparity of age, he knew how to lower himself to the level of the boys, as he also did once in a while as learning director of Camp Torah Vodaas. Despite being a tremendous talmid chochom he would not hesitate to referee a baseball or volleyball game. Despite his stature, he never made the boys feel naarish, nor did he put anyone down.
The menahel of an extremely distinguished mosad haTorah called me to relate that when he was a kid on Long Island, before Purim, he did a little shtick (probably tame by today’s standards). He left a cigarette on the rebbi’s desk for Rabbi Pressman.
Unlike a rebbi, who would push it away, Rabbi Pressman took it stride and said, “You gave me a cigarette, but you didn’t give me a lighter!”
“Don’t worry,” the boy said, as he pulled out matches from his pocket.
Rebbi said, “You gave me something, so I am not going to refuse.” He lit the match, lit the cigarette, took a puff, that was yotzei, and then he put it out and said, “Thank you and now, let’s learn.”
The menahel recalled fondly, “I felt like a million bucks.”
Of course, his class was the jewel of the yeshiva, and every distinguished guest from my zaide, to Rav Simcha Wasserman, Rav Gifter, Rav Chodosh, among others, was always brought to Rabbi Pressman’s shiur.
During the last seven or so years of his teaching career, he published a sefer with each class called Boruch Shekivanti, a collection of questions his talmidim had asked in which they had been mechavein to a Rishon or an Acharon or even a later rosh yeshiva. The vast bekius he had in the words of the Rishonim and Acharonim was astounding. It was fascinating to see typed in Hebrew “Boruch Weissman asked the following.” Then the gemara and the question were explicated in lashon kodesh sometimes with an answer, other times with only a question, followed by, “And he was mechavein to …” Rav Akiva Eiger, Pnei Yehoshua, Chasam Sofer, Rashba, Ritva, Rashash, Reb Elchonon, or Rav Chaim, etc.
He was always talking in learning. Always a vort, always an idea. Rabbi Dovid Kramer, the executive director of the yeshiva, told me “No matter the discussion in the financial office, Rabbi Pressman never left without a vort.”
A melamed, who lives in Jacksonville, Florida, spoke to me the day after the petirah. He explained how rebbi’s calm and even-keeled approach together with a moshol or melitzah, helped resolve what kids would consider a crisis.
The boys had mishmor, for which they ordered pizza and fries. Fortunately for the 25 boys, there were 25 slices (one was enough back then). Unfortunately for the boys, there were only 22 portions of French fries. Four boys were very disappointed. But who would not get?
“Rebbi calmed us down with a story, ‘Boys, don’t start your french fries.’ He said, “I’ll tell you a story: A man was driving, and had a flat tire. He took off the flat tire and wanted to change it. Suddenly the tire bolts fell off, and they fell down the sewer drain. He didn’t know what to do. All of a sudden, somebody screamed out from a building, and said, “Mister, I’m watching you, just take one off from each tire, and you’ll have enough for this tire.”
The talmid told me that the kids, at first, did not catch the moshol, until rebbi explained, “You don’t understand the nimshol! There are four boys that don’t have French fries. Everybody give; you have 24, everybody give four french fries into a bowl and we will have 80 more to divide up, and everyone will have an equal amount of french fries! You’ll be okay.”
The talmid, now an experienced mechanech chuckled as he said, “I remember that today, especially when I had a flat tire, and lost my hubcaps!”
Besides the hundreds of boys he taught, there were scores of Five Towns baalei batim who learned with him privately both before and after yeshiva. Many of them kept a close kesher, even coming to learn in the last years when Rabbi Pressman was in the assisted living center.
The young boy from Providence with the picture of the Ponovezh Rov impacted the widest range of talmidim by inspiring them to accept upon themselves small hanhagos that lasted for years. I received a copy of a post from one of his students who lamented the loss of his rebbi through a tweet, as they call it, on his rabbinical outreach page. “Since our baby was born, I’ve taken on the tradition of reading the parsha to him twice and Onkelos once. I had been meaning to call Rabbi Pressman to thank him again for this absolute privilege. We have lost our teacher.”
Although Rabbi Pressman did not return to the classroom after Covid, an entire generation at the Yeshiva of South Shore can say “We lost our rebbi.”
