At the 1991 U.S. Open, Haber slipped a $20 bill to a tournament worker on a cigarette break and snuck into Louis Armstrong Stadium, where he witnessed 39-year-old Jimmy Connors defeat Aaron Krickstein in a fifth-set tiebreak during round 4—one of the greatest matches in Open history. “To this day, that was the most exciting sporting event I’ve ever been to,” says Haber, who recently signed a five-year extension with the Tennis Channel as a host and play-by-play announcer.

Haber, who grew up in New York and has covered the Olympics for NBC, made his Tennis Channel debut in 2004. Since then, he has covered the four major championships alongside tennis greats, including Martina Navratilova, Lindsay Davenport, Tracy Austin, and Jim Courier. “Brett sets the standard for all of us at Tennis Channel with his preparation,” Courier says.

At 15, Haber was a kid correspondent on NBC’s teen magazine show Main Street before interning at The Today Show. During his freshman year at Dartmouth, he taxied his way to White River Junction, Vermont, every night to serve as floor director at WNNE TV. When the sports anchor left, Haber, an English major, turned down the full-time position. Three years after graduation, he became the youngest anchor in the history of ESPN’s SportsCenter. As the “de facto tennis correspondent,” he rekindled his lifelong passion for the sport. For Haber, who never played competitively and considers himself “a very average player,” covering championships with legends of the game is a hefty task. “I take it as an immense responsibility to not let them down and not let the viewer down,” he says. “To take all that preparation and make it come out the other end as an easy watch is the challenge that I love every day.”