Game Point
| December 24, 2024Yosef Yitzchak Gershon learned it’s never too late to shake off the past
By Yosef Yitzchak Gershon as related to Barbara Bensoussan
Yosef Yitzchak Gershon went from perfecting his tennis serve to serving time, but along the way he learned that only Torah holds the key to real healing and peace, and that it’s never too late to shake off the past
IFyou saw me today, in traditional chassidic garb on Shabbos, or on the tennis courts teaching or playing in tournaments during the week, you’d never guess that I was once on the most-wanted list of Broward County criminals in Florida and spent months in prison.
The pasuk in Hallel, “He raises the poor from the dust, and the needy from the garbage heap,” resonates with me deeply. Hashem pulled me from the muck of substance abuse and criminal behavior and raised me to where I am now, living life as a frum Yid, happily married and blessed with children.
For a long time, I wanted desperately to simply run as far as possible from the sordid parts of my past. Yet I learned the hard way that our shadows follow us no matter where we go, and the only way to go forward is to face our mistakes head-on. I’ve learned to draw strength from knowing that Hashem’s love is boundless, even for those who have strayed very far. But let’s start at the beginning.
Self-Destruction
My parents’ marriage was destined for challenges from the start: She was American, he was Israeli, and their perspectives on many things diverged. Still, despite their different backgrounds and lack of Torah education in their early years, they both did their best to raise us.
My father threw himself into everything he did with passion. He had a deep love for tennis, and when he saw that we kids showed promise, he was determined to cultivate it. He decided we would move to Florida, with its year-round good weather and many tennis academies, to give us our best shot at success. When my sister and I started winning tournaments, he took us out of school and arranged for us to be homeschooled to leave us more time for practice.
This promising future took a dive when my parents’ marriage fell apart. I was about 15, and I took it hard. I started rebelling and drowning my pain in reckless activities like driving my dad’s V8 Cadillac down the highway at 115 miles per hour. I was getting speeding tickets every week and blew two engines, but I relished the negative attention.
As my parents navigated their personal challenges, I went to spend the summer with my paternal grandparents in Tel Aviv. Saba and Savta have always been a strong anchor in my life, traditional Jews and straight, honest, good people. But Tel Aviv is a big city, and that summer I discovered alcohol. I met people who brought me to clubs and offered me hard liquor. Wow, I thought. This stuff takes away all the pain.
When I returned home after the summer, I found that my father had moved into a local hotel, tennis was on hold, and I had to go back to public school. My mother had started seeing someone, a guy I couldn’t stand. One night he showed up at the house to find me lounging on the couch watching television, surrounded by mess. “This is how you clean up? I have to walk in and see this garbage?” he yelled.
“Clean it up yourself if you’re not happy,” I retorted indifferently. More words were exchanged, and we got into a fist fight that my mother had to break up. A few days later it happened again. This time he came after me with a baseball bat, with my mother and sisters screaming at me, “Leave the house!” Somebody must have called the police, and they showed up looking surprised (our West Boca neighborhood was usually quiet and peaceful). The police strongly suggested that I go spend time with my father, so I moved into his hotel.
I was miserable. I felt very alone and was struggling with the changes happening in my family. Then my best friend Tomas introduced me to drugs, and we’d get high every night. I dropped out of school after getting into a fight with another student. Things were unraveling.
My father found me a job in a car dealership, selling Chevrolets. I really liked it. It was my first real job, and I was good at it — at one point I was the #2 salesman at the dealership. But in the evenings, I was out late every night doing drugs and alcohol.
One “friend,” Bill, a rebel-without-a-cause type with a cigarette forever in his mouth, introduced me to prescription pain meds, which I thought were great. It numbed all the pain of losing my once-happy family and my career in tennis. (Tragically, Bill passed away suddenly not long after we met, but I wasn’t ready to confront just how dangerous the path I was on could be.)
One side effect of the meds is serious lethargy. One Saturday, which was the biggest sales day at the dealership, I fell asleep for two hours in a back room. My colleagues got worried and came hunting for me. But no one censured me because they felt sorry for me. Unfortunately, that only enabled my addictive behavior.
I quit the job that summer. I was turning 18 and just wanted to spend time on the beach drinking and getting high. One night, as I was dozing on the couch watching a movie, Tomas called. It was midnight.
“Did I wake you?” he said.
“No,” I lied.
“I’m coming over, I’ll be there in 15 minutes,” he said.
I went back to sleep, and Tomas got on his motorcycle. But he never showed up. He got into an accident on the way over and was killed instantaneously. I found out the next morning.
I was devastated and overwhelmed with grief. This was more than I could handle. I couldn’t process that Tomas was gone, just like that. I couldn’t imagine life without him. I spoke at his funeral, numb with shock. I gravitated toward his family, the people who most shared my grief, and became friendly with his younger brother Luis.
The next year I began trying to get my life back on track. I started playing tennis again and training while living in an apartment with my sisters (the situation at both of my parents’ places was untenable for us). I was mostly off drugs and my old crowd of friends.
There were two players at the club named Sayid and Abdul, who were Moroccan Arabs. My father urged me to practice with them, because they were good players. I resisted at first. I didn’t like their vibe; there was something unsettling and frenetic about their manner. But my father pushed, and in the end, we became friends.
Sayid and Abdul introduced me to a next-level night life, clubs where people would arrive at 1 a.m. and party till 4 or 5, dancing to techno music. One of their friends mentioned, “You know, in these fancier clubs, people often leave their cars open, and it’s super easy to steal pricey items like Prada sunglasses or find cash or credit cards.”
“How do you do it?” I said.
He showed me his method, and later Sayid, Abdul and I found an open BMW in the parking lot with a couple of hundred dollars’ worth of merchandise in the back seat. We felt like we’d hit the mother lode — we’d found easy ways to acquire material things, falling deeper and deeper into bad habits. Every night we’d go to upscale areas and spend an hour or two stealing things, piling them up and pawning them later.
For now, I’d successfully numbed my pain over my family situation. Between the adrenaline of stealing and the heavy drugs, I was riding high.
I moved in with my Moroccan friends and their father and spent my days bulking up in the gym and going out at night. Tomas’s brother Luis began coming to the gym with me, and I told him what I was doing in the evenings. “Maybe you want to join me,” I said.
Luis became my getaway driver and my exploits went up a notch. We’d go to fancy restaurants, and I’d grab a purse from a table and run to the car where Luis was waiting. One night, I found a gun in an unlocked car and foolishly hid it in an attic. At the time, it gave me a sense of control and power.
My behavior became more and more brazen. One night I decided to go to Walgreen’s with my gun. I wasn’t planning to shoot — just to threaten the cashier to give me everything in the till. I put on a black shirt, black pants, and a black balaclava over my face and was heading out the door when Sayid came home. “Where are you going?” he demanded.
When I told him my plans, he protested. “No, no, no. I’m not letting you do that.” He probably saved my life.
As time passed, I began to feel that Someone was watching out for me. I was saved from irreversible trouble too many times to attribute it to a natural explanation.
Another time, I contemplated grabbing envelopes from people who exited a bank after making a withdrawal. Luis was supposed to spot them with binoculars as I hid, then signal me with a walkie-talkie to make my move. Somehow, thankfully, that never panned out either.
My family sensed that I was struggling, but I was unable to open up to them. Why stop this life? I figured. No one really cares anyway. That was patently untrue, but it was a way to justify myself.
When Luis and Tomas’s dad bought Luis a two-bedroom apartment, he invited me to move in with him, which I did. Our lives revolved around the gym, the beach, drugs, and stealing at night. He and I would go to restaurants to eat, fill up on food, and run out without paying. We were lucky no one ever caught up to us. One night, we did hear police cars with sirens, but we turned off the road and no one found us.
The Law Catches Up
One day, I was sitting in a recliner in Luis’s apartment, watching a heist movie on TV, when I heard a loud, aggressive knock. Looking through the peephole, I saw a guy wearing a suit. I figured it was probably a neighbor, so I opened the door.
“I’m Officer John Donno,” he said. “Can I come in?”
He didn’t wait for an answer. He pushed past me into the apartment and immediately handcuffed me. “Are you Luis?” he demanded. “I’m looking for Luis.”
“I’m not Luis!” I said. “I’m Joseph! Look, here’s my license!”
After examining my license, he uncuffed me. “Call Luis and tell him to come,” he commanded.
I tried to manipulate the situation to my advantage. “Do you want me to come with you, to answer any questions?” I volunteered, pretending I wanted to be helpful.
He gave me a sideways look. “Just stay here,” he said. “If we need you, we’ll call you.”
The minute he left, I grabbed a screwdriver and hid my gun in an air vent, then sprinted down all nine flights of stairs. My cell phone was blowing up with calls and I turned it off, worried I was trackable. I hid, then called my mother at midnight. “Come get me,” I begged.
My mother, always caught between her conflicting responsibilities, couldn’t come right away, but promised to be there first thing in the morning.
I hid all night, and she picked me up at 6 a.m. She brought me back to the house, where I hid in the garage. Later that day she called my father, and they arranged to put me on a plane to Los Angeles, where my father was now living. I was sweating bullets at the airport, terrified someone would identify me, but I got away without incident.
After that shock, California was a tonic. It helped me turn my life around. I was away from my low-life friends. The scenery in Beverly Hills was uplifting, and we were around many successful people. No one knew my background, and they were all friendly. My father would take me in the mornings to the Coffee Bean café and we’d have breakfast and talk, slowly reconnecting.
My father was strict with me. He charged me with walking his dog, a poodle named Coco, every day, and pushed me to take on responsibilities to build discipline and character. At first, I resisted. “What? I’m not doing that!” I’d protest.
“Yes, you are,” he said. “You have to start behaving like a mensch.” Over the next six months I began to behave more like a normal, law-abiding citizen, and I realized the importance of accountability. Once I stole a pack of gum, just to feel the sensation of getting away with something again, but then I thought, Nah. I don’t want to go back to that life.
One morning, at the café, I mentioned to my father that I still had a dream to win the US Open tennis tournament one day. My father immediately got a gleam in his eye. “Let’s do it!” he said. “Let’s start training!”
For the next year, I trained five or six hours a day on the tennis court. The discipline was good for me, and a year later, at 22, I beat a retired player in a practice match, a guy who had been #18 in the world. I was ready to jump back in to professional tennis.
Along with my personal rehabilitation, I also started feeling my way toward Yiddishkeit. My father had an upstairs neighbor, an Israeli, who invited us to come with him to shul on Shabbos morning. It was a Chabad minyan of mostly Sephardi Jews led by Rabbi Ishai Gabbay, and the men were warm and welcoming. I found a Tanya lying around and began reading it, and it struck a chord in me. Soon I began learning the sefer with the rabbi’s brother.
When Elul came, I began waking my dad in the mornings and taking him with me to Selichos. The people were nice, the niggunim stirring, and there was always a great breakfast afterward. A year after I’d run away from Florida, I was now in a very different place.
When Yom Kippur arrived, however, my past sins weighed so heavily on my conscience that it was like my very soul was being crushed. I sobbed so hard in shul that people turned around to look at me. I promised Hashem that day that I would make amends, turn myself in, and stop living like a fraud.
Serving Time
Later that week, I decided to Google myself and I almost fell over in shock. My name came up on the Ten Most Wanted list in Broward County! I was on the same list as a terrorist and a gang leader! I was wanted for robbery and battery, and those two charges in combination were considered serious stuff.
I still had Detective Donno’s card. I went to a pay phone, since I didn’t want to be traced, and called him. “I’m coming back soon, and I’m going to turn myself in,” I said.
He was speechless. It was the first time someone had called to offer that. “Okay,” was all he could muster.
I was determined to make amends with whomever I could. I called my saba, who had been so good to me even while I continually disappointed him, and I called Luis, who had been detained but had gotten off with only house arrest as he was still a minor. He hung up on me. I tried several times, but he refused to take my calls.
Slowly, I was becoming more religious. I put on tefillin every day and let my beard grow. But I couldn’t deal with the dissonance of being a Torah Jew and a wanted criminal. One day, I took all the money I could find in our kitchen, a few hundred dollars, and went to catch a Greyhound bus to Florida. (I was afraid to get on a plane). When I told my father, he didn’t discourage me. He came to the station to bid me success.
The ride was grueling; it took almost six days to cross the country. At one point US immigration control officers came on the bus. I felt panicky, but they were only looking for illegal immigrants. Another morning, as I put on my tefillin, a man near me started yelling, “This guy is trying to blow up the bus!”
Finally, I arrived at my aunt’s house in Hallandale Beach, Florida. I found a shul and began going every day. Meanwhile, my father put me in touch with a lawyer, who warned me to stay put until he told me what to do. In the meantime, seeking guidance and support, I confessed everything to the rabbi of the shul, Rabbi Raphael Tennenhaus.
“I feel terrible for you,” he said with genuine care. “But given all these challenges, for now you need to focus on resolving your situation in the right way.”
So I stayed home. One day, looking out the window, I saw an old man in a wheelchair. One day I’ll be old, I thought. I don’t want to look back at my life and think I was a failure. I have to move forward.
On impulse, I picked up the phone that night and called 911. “I want to turn myself in,” I said. “I’m a wanted criminal.”
“I can’t help you,” she said. “This line is for emergency calls.”
I couldn’t believe it. It was the stuff of comedy. We went back and forth, but she insisted she could do nothing. Finally, I called Detective Donno. “It’s me,” I said. “Can you come get me?”
“It’s 11 at night!” he said. “I’ll get you in the morning.”
The next morning, I put on my Shabbos clothes and waited for him. “Don’t do it,” my uncle pleaded.
“We’re outside,” the cops announced.
I walked outside to find five U.S. marshals — the guys who deal with the worst of the worst — waiting for me with their guns drawn. They looked confused. Here they were on a nice suburban street, and the perp comes out in a suit, tie, and kippah. They cuffed my hands and ankles and took me away in a van.
At first they were friendly, but I realized they were fishing for a confession, and I kept my mouth shut. That changed their attitude. We arrived at the precinct, I was hustled through a gate and told to take off my clothes and put on a jumpsuit. I wasn’t even allowed to keep my tzitzis.
After about six hours sitting in a cell, I was put in a van with metal seats, with six other prisoners. We were driven to the county jail, which houses reckless drivers and murderers equally. We were fingerprinted, processed, and brought to cells. I felt like an animal among animals, completely degraded as a human being.
I shared a cell with a man who had committed a murder. I barely slept, and there was no kosher food. Not sure what I could eat, I survived on packs of peanut butter crackers.
I saw the other prisoners eyeing me, trying to assess where I would fit in to the prison hierarchy. I decided to follow the lead of Dovid Hamelech, who acted crazy to stave off his enemies. I made crazy gestures and muttered to myself, and they gave me space.
A couple of days later I was moved again, to a large jail with thousands of men. I found myself in a cell with five hardened criminals. I got onto my bunk, shrunk into a corner, and put my blanket over my head. One of the guys started poking me, saying, “Hey, you!”
A man they called Red because of his reddish beard, said, “Leave him alone!” Hashem had sent me a defender. After that no one bothered me.
I spent 30 days there. Prison had a rigid structure of meals, recreation (shooting hoops and television), and sleeping. There were no work opportunities, classes, or a library. The Aleph Institute sent me a Tanach, although at the time I lacked the resources to understand it properly. Nevertheless, I greatly appreciated having it; it felt like a lifeline.
A Chabad rabbi, Mendy Katz, got me tefillin, which I wasn’t allowed to keep in my cell. In the mornings I would be brought to the basketball court, handed a manila envelope with my tefillin, and allowed to pray for a few minutes. On Friday nights, I would sit with another two or three Jewish guys, wearing my kippah, and we tried to have Shabbos together. A rabbi came on Chanukah, which was uplifting.
I did feel that Hashem was always with me. I had made a commitment to myself to not be influenced by my environment and would remind myself I had done the right thing. I looked for opportunities to make a kiddush Hashem or do chesed, to create points of light in the darkness.
That’s not to say it wasn’t really hard. In that environment, being violent was considered normal, and many inmates felt no remorse for their crimes. Their attitude was, “This is who I am.” I was with many people who live at a really low, animalistic level.
My mother visited twice, but talking to her through a plexiglass shield was devastating for both of us. There were moments when I fell into a deep emotional hole. At night I would feel myself surrounded by dark energy, as I listened to cellmates reminiscing about their adventures with drive-by shootings, gang violence, and the like. One night it caught up with me; I came very close to a panic attack.
After a month I was brought to a pretrial hearing for robbery and battery. The latter charge made no sense, because I never attacked anyone physically, but the combination meant I was not eligible for bail. The judge offered me a public lawyer, but the thought of being defended by some bumbling incompetent fellow frightened me. When I called my family, they insisted that I take a top lawyer, David Bogenshutz. My saba even took a loan to help pay for him. Despite the anguish I’d put them through (and vice versa), family is family, and in my times of need they always rallied for me.
I went back to jail for another month. Then, one morning at 6 a.m., a guard appeared, to take me to court. “Red,” who was looking at a 45-year sentence for assault, told me, “You are blessed. You are lucky.”
I met David, the lawyer my family had procured for me, and he told me he’d worked out a plea deal that involved two and a half years of house arrest and five years of probation. It sounded like an awfully long time. Maybe I should take my chances with a jury, I wondered? “This is a great deal! Take it!” the lawyer insisted.
I still hesitated. “You better sign these papers!” he yelled. I caved, deferring to his counsel.
Life after Prison
Upon my release, I went to live in my mother’s house in Boca, with an ankle bracelet and strict restrictions on how far away I could go. There wasn’t much to do at home, but I soon found the Chabad Israeli Center down the street, where the rabbi and his rebbetzin took me in like family and their children looked up to me like an older brother.
I spent time on the computer trying to learn Torah, although at the time I was still quite ignorant and had no idea how to go about learning on my own. One day I landed on a site called torah.org. There was a chat box, and I asked the rabbi on the other end, “Did Adam say a brachah when he ate the forbidden fruit?”
I don’t remember getting an answer, but we chatted for a long time, and he directed me to Rabbi Saj Freiberg in Miami, about 45 minutes away. He, in turn, helped me enroll in Chabad’s Yeshivah Torah Ohr, and I got permission to travel to Miami and back every day.
One night I fell asleep in yeshivah. The next morning, I woke up in a cold sweat. I had broken curfew! But nothing happened, so I did it again, and finally just stayed in yeshivah full-time.
Honestly, I don’t know what would have become of me without yeshivah. Coming out of prison unleased an emotional tsunami within me. I still felt guilty about my past life, but now that I was out of jail and my adrenalin spent, I had no idea how to process my thoughts and feelings. Yeshivah gave me structure, family, and a framework to channel my thoughts and feelings.
I began learning b’chavrusa, particularly drawn to chassidus. I bonded with my study partners, young men who were so pure and far from the life I’d left behind, yet so loving and nonjudgmental. I joined them in outreach activities, and Friday afternoons found us in supermarkets and shopping centers encouraging people to put on tefillin and light Shabbos candles. Dancing with an elderly man who had recently lost his wife, we all had tears in our eyes. I didn’t even mind when I was recruited to help with unappealing tasks like Pesach cleaning, scraping gum off the bottoms of chairs.
On Friday nights, different families would host bochurim; I was deeply impressed. I’d never seen such wholesome, harmonious families.
The yeshivah brought in speakers such as Rabbis Manis Friedman and Y.Y. Jacobson, and I was able to get permission to travel to Crown Heights for Tishrei. (The judge who granted me permission was Jewish and familiar with the concept). Being in Brooklyn, where my rebbe had lived, was deeply inspiring.
I soon received word that my sentence had been cut in half to only one year with the ankle bracelet, and only one and a half years of probation.
My family thought my new religiosity was a phase, a reaction to the trauma of jail, but as time went by, I felt just as attached. I believed Hashem had saved my life, and the least I could do was pay it forward by serving Him. I took up professional tennis again, becoming one of the fastest servers in the world. I found a club that didn’t hold tournaments on Shabbos, and also found my bashert.
When I met my wife, Elisheva, she was a baalas teshuvah waiting to happen. Our backgrounds were similar; she also came from a divorced, Israeli family. Once the relationship became serious, I felt obliged to tell her that I’d done time. She didn’t know all the details, but she was completely accepting and nonjudgmental. “You were young and hurt, and you made bad choices,” she said. “I also made some bad choices as a reckless teen.” Her father had owned nightclubs, and she knew just how depraved that scene can be.
Today the two of us live a life of Torah and mitzvos, and are grateful every day that Hashem helped us find the right path. I’m very close to completing semichah with Rabbi Aryeh Citron in North Miami Beach, and have become close to Rabbi Sholom Lipskar. I’m a professional tennis player and hope to use my talents to make a kiddush Hashem in the world.
I’ve learned that we aren’t defined by our past, and we should never be ashamed of it. I’ve shared my unhappy story to encourage others to realize that they, too, can reclaim their lives, no matter how impossible it may seem. Our darkest stories hold the potential for the brightest transformations.
(Originally featured in Mishpacha, Issue 1042)
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