His friends Naomi Osaka and Coco Gauff told him he belonged at the top level of the sport. But Eubanks wasn’t certain he could live up to that as a player. So maybe, he thought, he could belong there as a broadcaster.

“Listen,” Eubanks told his agent in 2021. “If I’m still [ranked] 200 by next year and injuries haven’t played a part, I can do something else with my time.”

That something else became a recurring gig as an analyst for the Tennis Channel. But it turned out to be more than an unfamiliar landing spot for a frustrated player just below the big time. The job off the court changed his entire perspective on it. And as Eubanks, 27, prepares for the first Grand Slam quarterfinal of his career, he credits that time spent in the commentary booth with reviving his game.

“It really helps my perception on the court,” said Eubanks, who had played all of 10 career matches at major tournaments before this summer’s Wimbledon. “I can take a little bit of the emotion out and say like, ‘Hey, if I were watching this match and calling it, what would I be telling myself?’”

At this point, Eubanks might be reacting the same as every other announcer around the All England Club, who can’t quite believe what he’s pulled off. The journeyman No. 43 who had never even survived the Wimbledon qualifying tournament first made some noise last week when he took down British No. 1 Cam Norrie in the second round, but he became appointment viewing here on Monday as he upset world No. 5 Stefanos Tsitsipas. Over the course of five thrilling sets, the 6-foot-7 Eubanks hit 13 aces and 53 winners to storm back from 2-1 down.

Immediately afterward, Eubanks sounded every bit the television pundit he’s learned to be when he trades in his racket and backward cap for a suit and an earpiece.

“The funny thing about tennis is that you’re not always going to play your best,” he said. “You’ve just got to play really good at certain times, and I feel like I did that really well today all around.”

Not even Eubanks could have predicted his charmed run at Wimbledon. He spends most of his time on the deeply unglamorous Challenger Tour, where tournaments unfold in front of mostly empty stands and players often get just one can of balls to practice with. Some off-court work—like the Tennis Channel or starring as Arthur Ashe in a recent CNN documentary about the player’s life—has raised his profile, yet even Eubanks admits that was still just an obscure long shot to reach the second week here.

As recently as early June, Eubanks was texting former world No. 1 Kim Clijsters for advice about how to handle grass courts because he was so frustrated. This, he wrote to her, was the “stupidest surface to play tennis on.”

Within a few weeks, though, he was crying tears of joy after winning his first top-tier title on the lawns of the Mallorca Open. His winning streak on the surface has now reached nine matches, setting up a clash with world No. 3 Daniil Medvedev on Wednesday for a place in the semifinals. Eubanks has already had to change his hotel checkout date in London twice after originally expecting to leave by last Friday.

“The grass and I, we’ve had a very, I would say, strenuous relationship over the years,” he said after beating Tsitsipas. “Right now I think it’s my best friend.”

Eubanks has a slightly different perspective on Medvedev than most of his opponents. He hasn’t merely played him this season, losing in the quarterfinals of the Miami Open. He’s also called a Medvedev vs. Alexander Zverev match for television. “He’s a master of problem-solving,” Eubanks said, back behind a Tennis Channel microphone on Monday as an interviewee.

Not only did reaching the quarterfinals guarantee him $439,000 of prize money—boosting his career total by more than 20%—it also granted Eubanks entry into Wimbledon’s Last 8 Club, a kind of airline frequent-flier lounge within the All England Club for anyone who has reached the quarterfinals of the men’s or women’s singles tournament. It comes with two lifetime passes to the Championships and a few other perks, which isn’t a bad reward for someone who had never played in the main draw at all here.

“I feel like I’m living a dream right now,” Eubanks said. “This is absolutely insane.”