Remembering my brother, Phillip Wintrob z’l


Phillip Wintrob z’l was just 17 when his life was cut short by a tragic car accident. At the time, he was in Grade 12 at a public high school and was co-leader of Shaarei Shomayim Youth together with his best friend, Danny Scherer.  The accident occurred while they were driving back from Rochester, having picked up kosher chocolates for the Shaarei Shomayim kids. Since no original eulogy from Phillip’s funeral is available, his family has put together this tribute:

On July 16, 1969, mission commander Neil Armstrong and pilot Buzz Aldrin of Apollo 11 blasted out of Florida’s Kennedy Space Center in an attempt to become the first humans to land on the moon. It turned out to be, in Armstrong’s famous words, “one small step for man, one giant leap for mankind.”

On that very same day in Toronto – while eyes everywhere were glued to their TV sets – another shining star blasted onto Earth. Though the event didn’t make international headlines like Apollo 11 did, it was just as astronomical and riveting for Ralph and Kitty Wintrob because that was the day that their long-awaited son, Phillip (Pesach Ari), was born. At 9 lb. 10 oz., he was big and beautiful and full of energy. His parents and six-year-old sister Suzanne fell in love instantly and their family was complete.


As Phillip grew, it was clear he was going to go places. He was a happy-go-lucky kid bursting with personality, with his mop of red hair, sparkling green eyes and huge smile always winning hearts. He loved to laugh- and what a wicked laugh he had!-and he relied on his charm and wit to get him out of trouble with his parents and teachers. He was a master of excuses who burnt incense in his messy bedroom to mask the smell of his dirty laundry. He could usually been seen skateboarding up and down the streets near shul, his tiny crocheted kippa flapping in the breeze. He got a kick out of playing the saxophone, baking birthday cakes and hanging out with friends. He never backed down from a healthy debate and wasn’t one to follow the crowd, feeling more comfy being different than conforming to rules. As he wrote in an essay for an Israeli scholarship application: “I like to get what I want. I will go to every measure to get what I want, especially if other people are counting on me to come through for something or another.”


For Phillip, life was about fun and friendships, not books and schoolwork. As he wrote in his essay: “Phillip as a student is not too great. Now it’s not that I’m stupid. It’s just that: 1) I don’t see how some subjects will get me through life, even if just for the sheer reward of knowledge, and 2) I never seem to be able to concentrate on school because of my extracurricular activities. But when I try to put full attention to a subject, or anything else for that matter, I think it gets done. And it gets done well.”

Phillip might have struggled to get good grades in high school, but it was during that time that he really found his calling. At 17, he and his best friend, Danny Scherer, took over as youth directors at Shaarei Shomayim when the regular leader got sick and couldn’t continue. He and Danny took their responsibilities seriously, rushing straight from school to their little office at shul to plan and lead programs, phone potential attendees and counsel kids looking bit of understanding. Phillip’s parents always knew where to find him, even at midnight, which was reassuring in a time before cellphones. Though the beloved caretaker, Mrs. Babos, got irritated when he left a mess behind or skateboarded up and down the shul’s halls, Phillip was always quick to turn on the charm and she never stayed angry for long. The highlight of his term was leading a Shabbaton to New York City that the kids talked about for years afterwards.


Phillip thrived as a leader and even had visions of one day becoming president of the shul. “As youth director, I love to handle problems and make these problems into perfect solutions,” he wrote. “I like to put smiles on people’s faces, people who normally wouldn’t because of being wronged or insecure.”

He did that not only by being charming but by listening and doing. On Shabbat, his office door was always open so kids felt it was okay to come in, seek advice or take an extra candy to sweeten their day. One eight-year-old boy, who’s now an adult, remembers it this way: “After getting blocked by a throng of those aggressive-reaching hands during one of the weekly door-prying Hershey’s candy distribution sessions at shul, Phil took me into the blue youth director’s office, opened all of the giant candy cupboards behind his desk and said, ‘Take whatever you like.’ It was a small gesture, and three decades later it remains an indelible and cherished memory of his genuine neshama.”

Rabbi Chaim Sacknowitz, Downstairs Minyan spiritual leader and family friend, had this take: “Behind a rough exterior and façade, there was a young man with a big heart who was sensitive and compassionate, to whom friendship meant something special. Like many teenagers, Phillip groped and searched to find himself and emerged as a youth leader at Shaarei Shomayim. He influenced the lives of hundreds of young people and he taught them the beauty of living Jewishly, often displaying his marvellous sense of humour.”


Living Jewishly was certainly Phillip’s thing. He was always sleep-deprived and could rarely get up on time for school, yet he had no trouble waking early on Shabbat mornings to learn the Parsha-Haftorah connection with family friend Eugene Feiger (in fact, Phillip made it a point to always sit in a straight-backed chair rather than the plush sofa if he was exhausted). Ever the debater, Phillip kept the elder man on his toes. Still, it was a highlight of both their weeks. Those chavrutah sessions started when Phillip was just 14 and lasted for three years, and were the source of many of Phillip’s messages to Bar Mitzvah boys when he presented them with a gift at the end of davening.

Said Mr. Feiger: “Phillip’s profound questions of certain biblical passages caused me to think and search. I can safely say that sometimes one can learn more from his students’ smart questions that even from your own teachers. Phillip had a great urge for knowledge. He would never miss a Saturday morning session, rain or shine, in spite of the fact that Friday nights he used to meet with his friends for an Oneg Shabbat and those sessions went on into the late hours. On the day that Phillip’s shiva ended, Ralph turned to me that Friday afternoon and said, ‘I wish to continue where Phillip left off.’ Ralph’s friends, Ron Beasley and Dr. Laurie Blendis, also joined and continued with us for many years. It was Ralph who was searching for meaning and asking all the questions, which made our learning lively and interesting.”


At just 17 years old, Phillip wholeheartedly believed that he was doing his share for the Jewish people. If a shiva needed a minyan, he’d hop on his skateboard to help out. If there was an opportunity for chesed in the community, he was there, no matter how difficult the circumstances. He spent a summer on an Israeli army program and hoped one day to make Aliyah. As he wrote in his essay: “If every Jew in the Jewish community did a bit of work for his fellow Jews, I believe that there would be a lot better harmony among Jews in the Diaspora. As a youth director, it takes all my spare time up and a lot of my sleep. It is for this reason that I can’t participate in many after-school activities. For me, Judaism comes first above all other things. It is the most important thing that I base my life around. It is for this that being a youth director at one of the biggest orthodox synagogues in North America is one of the biggest thrills in my life.”

Yet with all his good intentions, Phillip never felt he was good enough. The year he was youth director, he was asked to daven Kol Nidrei for the youth minyan. He prepared himself as he had learned must be done but said he wouldn’t do it again until he measured up to his holiness quotient.


Our last photo of Phillip, Mother’s Day 1987

Who knows how Phillip would have eventually fulfilled his calling, as he saw it, as an agent in Tikkun Olam. He was never discouraged. He always saw, even at his young age, new levels of possibility. As he wrote in his essay: “I hope to finish high school and go to university. I plan to take general history and get into law. I love the courtroom. I enjoy the thrill of democracy. The goals I have for my extracurricular career are that I hope to build a good name for myself within the Jewish community of Toronto. I would like to put a lot more volunteer work into helping people who are not as fortunate as I am.”

In Phillip’s good name, therefore, may we all be worthy to strive, as G-d’s partners, in perfecting the world, of helping to transform chaos into cosmos at whatever level we are able. Because, after all, one small step for man is one giant leap for mankind.


This article was originally published in Shaarei Shomayim Congregation’s High Holiday Reader 5777, October 2016

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