“You can hear that he’s a professional by the sound of his racket hitting the ball.” Yosef with Francesco Migliano, assistant director at Sportime, tennis coach, and his sparring partner today

A Passion Passed On

Yosef’s parents were a mixed marriage — his mother is American, his father is Israeli. Yosef is the second of five children and the only son.

His father Ehud grew up in Tel Aviv, and his passion for tennis was first ignited at 17, when he watched the 1975 Wimbledon finals between Jimmy Connors and Arthur Ashe.

“I began practicing constantly,” Ehud Gershon tells Mishpacha. “I was out there rain or shine.” He was soon playing with then-Minister of Defense Yitzchak Rabin, who was the neighbor of a friend. Rabin would come in his car, often with his wife Leah, to pick Ehud up and drop him off at home for every practice. But then Ehud got drafted into the army, and he had to drop the game.

Ehud came to the US after his army service, working as a stockbroker at Dean Witter Reynolds as his family grew. In New York, he found tennis again. When his oldest daughter Sheryl was three, he handed her a tennis racket and was struck by an epiphany: He may have missed the boat to tennis stardom, but if he began training his kids young, the dream would be within their grasp.

Two years later, two-year-old Yosef was old enough to hold a racket and start training too. Father and son began spending hours at the Alley Pond Club in Queens.

“He used to come straight to the indoor tennis courts in his suit and play in his socks, since they don’t let you in with street shoes,” Yosef recalls.

“I saw my children were athletic and maybe could become champs,” Ehud says. “We trained together. It kept the family close, and I thought it was a better pastime for them than watching television or other stuff. My oldest daughter was very disciplined and a hard worker, but in the end, she didn’t have the drive. Joey didn’t listen as obediently — he had to do things his own way — but he was more competitive. He liked to win.”

Tennis bonded them. Ehud never missed a practice with his children, even when he was on crutches for a while after an accident. If he had a conflict in his schedule, he’d go to the courts later, even at one o’clock a.m.

Yosef won his first eight-and-under junior tournament at age seven. A few years later, Ehud Gershon quit his job, moved the family to Florida, and dedicated himself to Yosef’s tennis career full-time, like a stage mother. “He made it clear we were going to get to the top,” Yosef says. “He liked to say, ‘The easy way is the hard way.’ ”

It wasn’t always easy for Yosef, whose personality was so different from his father’s. “My father can be tough; he has that Israeli-army mentality,” Yosef says. “I’m more of a sensitive person, so there were times I wanted to do other things, more of the regular teen things. The strict training regimen was overwhelming sometimes.” The move to Florida was also tough for him. He didn’t like the hot, steamy weather, and he struggled to adapt to the slower pace of life. Mostly, he missed his friends. The kids in Florida made fun of his New York accent, and being so tied down to tennis meant that he didn’t have the time it takes to develop friendships.

Sheryl and Yosef were enrolled in the Chris Evert Tennis Academy in Boca Raton, and by seventh grade, they had been taken out of school for homeschooling. Yosef trained on the courts four to five hours a day; life revolved around tennis.

Pintele Yid

Yosef’s family was strong on Jewish identity, but unacquainted with observance. Still, his parents threw a lavish party for his bar mitzvah, and his father’s grandmother, Savta Leah, told him, “You have to put on tefillin now.”

“Savta Leah’s father was a rabbi. I saw black-and-white pictures of him with a long beard,” Yosef recalls. “My great-grandparents were traditional, they kept separate meat and milk dishes. I remember going to their house. They’d serve us rugelach and my great-grandfather would give us money as a gift.”

Savta Leah’s words remained in his mind, stoking the pintele Yid inside him, and one day he decided to go to a synagogue to find out what the tefillin thing was all about. Thirteen-year-old Yosef walked into the nearest shul, a Chabad house, and asked about putting on tefillin. Rabbis Boruch Shmuel Liberow and Zalman Bukiet were astounded. “You came here all by yourself at 8:30 in the morning? That’s amazing! You have to come speak to our youth group!”

Hey, easy, I’m no speaker, Yosef thought. But he went home and told his family, “This is beautiful.” He enjoyed the prayers and the feeling of being part of something bigger than himself. That year, he and Sheryl fasted on Yom Kippur for the first time, even though it was really hard. He began attending shul more often and was able to convince his family to join him sometimes.

That year, Yosef began to flourish as a tennis player. “Maybe my bar mitzvah and all the family and community support imbued me with the confidence that I could do great things,” he speculates. He scored an 18-2 winning record in his age group and won a handful of tournaments, as well as the competition for the fastest serve at the Citrix pro event in Delray Beach, Florida. “I served a ball that went 117 miles per hour in front of a stadium full of people,” he says. “I took home a check for $1,300, and I was one happy kid. I was happy to make my dad proud, happy to see my hard work pay off, and happy to buy my first computer with that money!”

Two years later, he twice won the same competitions for the fastest serve in the 18-and-under category, smashing balls at speeds of 124 and 127 miles per hour. Andy Roddick, a world champion, attended the competition and remarked, “I didn’t serve like that at his age!”

The months passed, and as Yosef won more competitions, the family home filled with trophies.

Of the 600 million people who watch professional tennis every year, not one has ever seen an Orthodox Jew compete at the highest level. Yosef Yitzchak Gershon plans to change that

Going Down to Go Up

In 2002, when Yosef was 15, his grandfather Robert died. Pop had been living with them while he battled cancer, and Yosef, who had helped care for him, felt very close to him.Without any shivah or spiritual framework to support him, he felt confused and depressed, spending many dark hours trying to puzzle out the meaning and purpose of life. “It really affected me,” he says. “I was having trouble focusing on the court.”

Around then, the Gershon family, and their tennis obsession, began to unravel. Yosef’s parents divorced while he was still in high school, and his sister Sheryl moved to Israel. Their mother remained in Florida and remarried. Ehud found a new passion, producing music and writing movie scripts, and left for California.

The changes left Yosef reeling. He lost his routine, structure, and sources of support, and intensely missed his father’s presence. At a loss, he dropped tennis completely, and he spent his time hanging out, going to the beach, and learning to surf.

He hung out a lot with his best friend, Alex, who was originally from Argentina. Both outsiders, they understood each other. But when Yosef was 18, tragedy struck again. Alex was riding his motorcycle to Yosef’s house, there was an accident, and he died.

“Alex was like a brother,” Yosef says. He was thrown into an intense period of mourning and grief. It took him a year to recover.

One day, as he struggled to climb out of the darkness, he spied his tennis racket. That’s the one thing I know, he thought. He began playing again here and there, but it didn’t satisfy him. The struggling 20-year-old shifted gears yet again, making the decision to move to Beverly Hills and live with his father.

The two of them were sipping coffee at a Coffee Bean one day when Yosef suddenly said, “You know, I still have a dream to win the US Open.”

Ehud Gershon didn’t blink. “Okay,” he said. “We’ll start training tomorrow.”

“The court has always been a place of new beginnings for me — regardless of what was going on in my life, I could start anew,” Yosef reflects. “Tennis has been like a small world where I could overcome my fears and inhibitions. Win or lose, it gave me a sense of purpose. I’ve believed, since I was a child, that anything was possible — my father instilled that belief, and it is that belief that has always called me back to the court.”

Yosef began training six hours a day.

Ehud explains the purpose of the training and the thought process behind it. “I didn’t overwork him,” he says. “We’d run on the beach, not on asphalt, to avoid taking a toll on the joints. He’d train two or three hours at a time, not five. Now, at 35, his body is still like a 20-year-old’s.”

After a year of intense training, Yosef was in better form than he’d ever been. During a practice game, he won 6-2 easily against Vince Spadea, once ranked #20 in the world and one of the only five people in the world to have won against Roger Federer, arguably the best tennis player player in history, 6-1 in a set. Spadea predicted, “I’ll see Yosef in the top 100 next year.”

But Hashem had different plans. Elul arrived, and a neighbor invited Ehud and Yosef to join him at the Chabad House in Pico-Robertson for Shabbos. He enjoyed himself, and started coming every morning for Selichos at 6 a.m. “They served this great tea and breakfast afterward — and the niggunim of the Selichos were very moving,” Yosef remembers. “It brought back my positive experiences from years prior, and I sensed that this was what I’d been searching for.”

He began wearing a yarmulke and putting on tefillin every morning.

Under the twin influences of his lingering losses and new exposure to Yiddishkeit, it was like Yosef’s neshamah, suppressed for so long, burst free.

“I sobbed through the Yom Kippur davening,” he says. “All the pain from my past, the regret and shame from the mistakes I’d made, and the sadness about how distant I was from G-d, came pouring out.”

The urge to connect to Torah was very strong. “I felt like Hashem was inviting me to Yiddishkeit, to a spiritual life,” he says. “I had to make a choice: follow this path, or take it easy?” Yosef committed himself to learning, approaching it with the same discipline he’d applied to tennis.

Yosef, now 23, returned to his mother’s house in Florida for a visit. One evening, close to midnight, he was surfing the Internet and discovered torah.org. Intrigued, he found the “Ask the Rabbi” button and typed in a question. “It was a beginner’s question. I asked if Adam made a brachah before he bit into the fruit,” Yosef says with a grin. “I don’t think I ever got an answer! But the rabbi and I had a long conversation, and he urged me, ‘Go see Rabbi Saj Freiberg in Miami. He’ll guide you in the right direction.’ ”

When Yosef knocked on the rabbi’s door early one morning, Rabbi Freiberg, then director of Aish’s Maimonides Fellowships in Miami, came running out with a three-year-old in tow. “Here, come with me!” he cried, loading the child into a minivan. He proceeded to drop off the child at daycare and then took Yosef on a tour of the local community.

Intrigued, Yosef opted to enroll in Chabad’s Yeshivah Torah Ohr in Miami, taking the train an hour every day from Boca Raton and learning a full seder until eight-thirty in the evening. He spent the next two years learning and growing and settling into Lubavitch chassidus as his chosen derech. Along the way, he met many rabbanim who left an impression on him, particularly Rabbi Y.Y. Jacobson and Rabbi Manis Friedman. Both encouraged him to pursue his dream of playing tennis professionally and to look for ways to inspire Jews. “Go into the world and show people you can do what you love,” Rabbi Friedman told him. “Use it to serve Hashem and be mekarev other Jews.”

Tennis had been the one area where he’d always been successful. Yosef resolved to figure out how to pursue it properly even within the constraints of a religious lifestyle. On a whim, he googled “tournaments not on Saturday.” The name Carlos Casely came up, at a club called Maxwell Park in Pembrook Pines. He called and was told the tournaments were held on Sundays through Tuesdays.

“I don’t know any coaches,” Yosef said.

“I’m a coach,” Casely replied.

The two took a liking to each other. Yosef describes Casely as a spiritual, moral person, and when Yosef admitted he had no money, Casely offered to train him for free, seeing potential in the young man. After a year of training, Yosef had won 25 tournaments and some nice prize money (most of which he gave Casely to cover his training).

He was grateful to be on his way again.

“I’ve always believed my purpose in life was to maximize what I was given,” Yosef says. “I get deep satisfaction actualizing my potential. The quest to master something, like running toward a faint and distant visual, has always triggered excitement for me.”

Yosef spent the next year training and playing tournaments while living with his mother, who has always been extremely supportive of him and his career. He was making great strides: his fastest recorded serve speed, 145 miles per hour, makes him one of the fastest servers in the world.

“When I play, I feel alive and unencumbered in my body,” Yosef says. “Time seems to stop on the court, and I get to use my mind to push past the limitations of my body.”

Going Forward

Yosef was scheduled to play in a tournament in Tunisia when Covid hit, and the world shut down. He used the forced quiet to continue training.

In 2020, as Covid restrictions eased, a friend from shul said, “I think you’d get along well with my niece, Ellie, from California — you two should meet.”

On the surface, the couple had little in common, and everyone they knew was initially skeptical. Only Ellie’s aunt and uncle knew both of them well enough to see how similar they were. There was an age gap of over ten years; he was religious, with a long beard and tzitzis, while she still wore ripped jeans and short sleeves. But both were sensitive souls from Israeli families who had gone through the pain of parents’ divorces, and they shared an inner longing for spirituality. “Our engagement was a head-scratcher for a lot of people,” Ellie admits, “but the community was so accepting, and I took on things little by little. I loved it! I had always wanted more connection to Hashem. I just didn’t know how to go about it.”

Yosef enrolled in Rabbi Aryeh Citron’s Yeshiva L’Smicha program in Surfside, where he and Ellie live. There he has become close to Rabbi Sholom Lipskar, the Chabad shaliach and community leader. He continues to attend the semichah program twice a week (he’s about halfway through). “He’s good with the learning, and he brings me sh’eilos when they come up,” Rabbi Citron reports. “We talked about fasting on days when he has a tournament and whether or not he’s permitted to teach girls.” (The answer is yes, until age nine.) “Tennis is a little out-of-the-box as a frum career, but you can find Hashem outside the box, too.”

With so many good tennis players out there, what propels a champion to the top?

“Tennis is challenging because you’re not part of a team,” Yosef says. “No one is coaching you when you’re out on the court. In that respect it’s kind of a lonely sport. You have to figure it out yourself.”

The best players don’t give up quickly and are able to adjust quickly when the game isn’t going their way. “They can be down in the match and still find a way to win,” Yosef says. “They strategize; they switch from Plan A to Plan B. They play their strengths to the other player’s weaknesses and manage to control the match even if the other person is having a great day.”

Does he get nervous before a big match? “I get nervous before, but not once I’m playing,” Yosef says. “Pete Sampras, one of the greats, says if you’re not nervous it’s not a good sign. Your body should be a little amped up.” His grounding in emunah and bitachon come into play, as it were, on the court. Competitive tennis is a tough world: “If you let your emotions take over even for a minute, you lose the point and lose the match,” Yosef says. “Tennis is a microcosm of life. You have to let your mind rule over your heart and maintain full focus.”

Unlike the players who lose their tempers, curse, or smash their rackets, he tells himself he’s doing his best hishtadlus, talks to Hashem in his mind, and adopts a gam zu l’tovah perspective.

Today, freshly out of shanah rishonah, Yosef puts in a full day of training and coaching for parnassah. He does not play games or tournaments on Shabbos, which hasn’t been a problem so far.

Six hundred million people watch tennis every year, Yosef notes, but zero have seen an Orthodox Jew compete at the highest level. He’d love to change that.

“Yosef proves that you can be religious and athletic at the same time,” his father Ehud says.

“I can have more success influencing the people I play with on the court than off,” Yosef explains. “Tennis breaks the ice; people think, ‘Well, if this tennis pro thinks Yiddishkeit is important, then it must be.’ ”

Complete and utter focus is the only way to succeed in this sport. Yosef Yitzchak Gershon hopes to climb the ranks and place in the world’s top 300 tennis players by 2023, the top 100 by 2024, and in 2025, to compete in the US Open

Inside Tennis

Tennis has been enjoyed by players since its invention in the 16th century in Europe (Henry VIII was apparently a fan). The game is played between two players (or, in doubles games, two pairs of players), and is played on clay, concrete, or (more rarely) grass courts. Once an outdoor sport, many clubs today are enclosed to allow for practices during inclement weather.

Using rackets, the players hit balls back and forth over a net. The objective is to return the ball to the opponent’s side within the boundaries of the court, and it can only bounce once before it is returned. When a player cannot return the ball to his opponent’s court, his opponent wins the point.

Tennis has unusual scoring, going from zero to 15 to 30 to 40; a 40-40 tie is called “deuce.” When deuce happens, the players must win two more points to win the game. A set is won by the first side to win six games, and a match won by winning the best of three or best of five sets (best of five is generally reserved for the highest level tournaments).

Players toss a coin or spin rackets to decide who will serve the ball in the first set. After that, they typically alternate serving. At the end of the game, it’s customary for players to shake hands and congratulate the winner.

Professional tennis is played under the aegis of the Association of Tennis Professionals (ATP), which holds events in cities all over the world. The events get corporate or local sponsors (like a Lexus car dealership or a sports equipment store) to raise the prize money. “You could play every other week in a professional tournament — there are lots of them,” Yosef says.

The cost to enter a tournament is minimal, but travel expenses can be high, and Yosef hopes to play in countries as distant as Tunisia and Australia. As players win tournaments, they ascend in their ATP rankings and are eligible for tournaments with higher purses. At the lower levels, players can win $50,000 or $75,000 at a tournament; at the highest levels — the ones televised worldwide — players can walk away with a couple million dollars.

Many players have agents, and Yosef is currently looking for one. In the meantime, his friends Neil Auerbach, Avi Goldstein, and David Schottenstein have been helping him launch his career (Neil has been managing it so far). Yosef hopes to climb the ranks and place in the world’s top 300 by 2023, the top 100 by 2024, and in 2025, to compete in the US Open.

(Originally featured in Mishpacha, Issue 931)