Hassan meets Christopher Eubanks in his Olympic debut.

In the regimented world of professional tennis, count Benjamin Hassan as an—affable—outlier.

“I’m a spontaneous guy,” Hassan told TENNIS.com ahead of his Olympic tennis debut with Lebanon. “I don’t plan stuff. I still play tennis because I want to have fun. The moment I don’t enjoy it anymore, I’ll stop.”

Emphasizing as much, his former coach, Dominik Meffert, recounted a recent conversation he had with the fast rising Flavio Cobolli that revolved around Hassan.

This month, Cobolli and Hassan played for the German Tennis Channel Bundesliga team Meffert captains, Kurhaus Aachen. When they were foes three years ago in Turkiye, Hassan beat the now world No. 48.

“We were talking about Benji,” Meffert told TENNIS.com. “Flavio said, ‘I played him a few years ago in a Futures in Antalya and he beat me. Now, I’m 48th and he’s 140th. We both made good progress, but he’s better than me, actually, as a tennis player when I look at the forehand, backhand.”

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He just does things the other way. These type of free thinkers, you cannot push too much. He’s not a typical professional who can be calm and silent and focused all the time on tennis. He lives life. Everybody loves him. It’s really tough not to like him. He’s so funny. —Dominik Meffert on Benjamin Hassan

Cobolli, though, “is an unbelievable professional,” said Meffert. “He loses Friday and gets up Saturday morning to practice again. Benji loses on Friday and maybe takes the weekend off and starts practicing on Monday.”

The former doubles No. 91 wasn’t critiquing the 29-year-old, mind you.

“He just does things the other way,” said the long retired Meffert, who first met Hassan at an exhibition. “These type of free thinkers, you cannot push too much. He’s not a typical professional who can be calm and silent and focused all the time on tennis. He lives life.

“Everybody loves him,” the 41-year-old continued. “It’s really tough not to like him. He’s so funny.”

Tennis Channel Bundesliga matches, which provide players with extra income, are well attended.

Hassan, however, graces his biggest ever stage when he competes with the likes of Novak Djokovic, Rafael Nadal, Carlos Alcaraz and defending men’s singles champion Alexander Zverev at Roland Garros.

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Currently ranked 170th—a little lower than the aforementioned 140th—Hassan earned an Olympic spot thanks to a Universality Place, essentially a wild card.

Hassan features in singles and doubles, and along with doubles partner Hady Habib, they comprise Lebanon’s first ever tennis entrants at the Games.

Lebanon, which counts a delegation of 10, last won an Olympic medal in 1980.

Hassan was born in Germany shortly thereafter and has lived there his entire life. He represents Lebanon in the Davis Cup, sporting a 13-6 singles record.

Tennis runs in his extended family. His dad, Zaki, went undefeated in six Davis Cup matches for Lebanon.

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Zaki and Hassan’s mom, Fadia, were both born in Lebanon and later met in Germany. Hassan sits in the middle of five children.

“Never was alone, actually,” said Hassan. “Just in my tour life, I’m alone. All my childhood I was always with them together. Of course, there’s been some tough times, but it’s been very nice.”

Those tough times relate to family, or more specifically, being away from them. It used to be harder, but “still now, traveling is tough. I don’t like to see airports,” Hassan said.

Of Hassan’s 10 Challenger semifinals, nine have come close to home in Europe. So have all three finals.

In one last October on Hassan’s favored surface of clay, Cobolli edged proceedings, 7-5, 7-5.

Despite the defeat, last season marked Hassan’s best, finishing 151st after previously never landing inside the year-end Top 300.

“I actually don’t know why that step came. Maybe it just clicked,” said Hassan.

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Hassan meets Christopher Eubanks in his Olympic debut.

Hassan meets Christopher Eubanks in his Olympic debut.

Then again, Hassan admitted to focusing more on his fitness, recovery and diet. Just don’t expect the 6-foot, roughly 187-pounder to lift many weights.

“I don’t do this kind of thing because the next day I have added five kilos (11 pounds),” he laughed. “I’m exaggerating but it’s crazy, really. I do one push up and I feel like I’m two kilos more the next day.

“I don’t have the physique of a tennis guy. I’m not that big, skinny, how you see some of these guys. I’m completely opposite to that.”

In another anomaly, Hassan didn’t play much from his early teens into his very early 20s. He lost motivation, only becoming reinvigorated when he received a wild card at his hometown Challenger in Koblenz in 2017.

Hassan won the first set before losing in three against the hard-hitting former No. 43, Teymuraz Gabashvili.

“Because I wasn’t practising, I wasn’t fit, and I lost,” said Hassan, whose game showcases variety. “But just keeping up with him gave me motivation. I told myself, ‘What happens if you try now?’ So I was curious what I can achieve. That was actually the start of my professional career.”

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I need to improve, but of course I can be proud of myself because I’ve done something for myself that was very tough, or which is very tough. I’m still hungry for more. —Benjamin Hassan

He isn’t overawed against higher-ranked opposition, evidenced by a 6-15 record against the Top 100. It suggests Hassan could pull off an Olympic scalp, even being one of the lowest-ranked players in men’s singles (putting aside protected rankings and replacement athletes).

“Benji has the level to qualify for an ATP event, then to win it,” said Meffert. “I think he has everything. On court, he has some abilities you cannot teach, with his shots, some movements, some anticipation. I’m sitting on the bench (during the Bundesliga), and I’m like, ‘He just has it.’”

Hassan additionally has a penchant for escaping from seemingly impossible situations.

He saved 12 match points across four different games to beat Lucas Miedler—his doubles partner that week—at a Challenger in Banja Luka in 2022. There were so many match points that Hassan lost track.

“After the match, someone told me, ‘Hey, you saved some match points, and I said, ‘Yeah I think four or five,’” Hassan recounted. “And then after, someone told me, ‘Hey man, you actually saved 12 match points.’ I said ‘What the f*?’ I didn’t believe it and then someone on (X) posted a video of all the match points. One unbelievable rally after another. It was crazy.”

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Hassan hopes to land a household name at the Olympics, citing Nadal, Alcaraz and Zverev.

When the Olympics are over—and having achieved another of his goals of playing in Grand Slam qualifying—next on the bucket list is to play in a Grand Slam main draw.

“I need to improve, but of course I can be proud of myself because I’ve done something for myself that was very tough, or which is very tough,” said Hassan. “I’m still hungry for more.”