On a warm New York evening inside Arthur Ashe Stadium, Justin Gimelstob got his chance.

It was 2007, and the American had just lost an entertaining match to his close friend and rival Andy Roddick. Retirement was imminent. Yes, there would be a few more matches before he officially walked away, but this would be the last on the biggest of stages. His body was breaking down, and Gimelstob had accepted, however reluctantly, that his playing career was coming to an end. This would be the last tennis he played on this revered, electric court.

While the outcome of the match had never really been in doubt (the final score was 7-6 (6), 6-3, 6-3) that didn’t make the final moments any less difficult for the New Jersey native. Or any less emotional. The 30-year-old right-hander decided to take his time exiting the stage and spent a few moments soaking in the atmosphere. He spoke to the New York crowd for the final time as a player. Gimelstob told a couple stories, cracked a few jokes, and then prepared himself for the curtain to come down.

But then a funny thing happened. The boisterous crowd wanted more entertainment. And if they couldn’t get a fourth set of tennis between Justin and Andy, how about some more conversation?

So Gimelstob, still dripping with sweat, took the microphone in his hand and did what he now does so well: He interviewed.

For close to five minutes, he joked, prodded and peppered Roddick with questions before an amused crowd. By the end of the sequence, Gimelstob had convinced America that he was ready to move into broadcasting, and had launched a second career.

“People think it was just a lucky break. Or good timing. And it was, to a certain extent,” Gimelstob said. “That moment was totally unplanned and totally unrehearsed. But people don’t realize how much work I’d put in with the Tennis Channel up to that point. That I had interned with them and studied the business with them…so that when my break did come, I was ready for it.”

That night sparked what is now a raging brush fire of a career. In five years’ time, Gimelstob has parlayed those New York minutes into a thriving livelihood that includes covering the Grand Slams, Davis Cup, and the Olympics for various broadcasting networks; providing commentary and analysis for at least a dozen of the smaller tournaments throughout the year; supplying a consistent flow of interviews and original content for the Tennis Channel through his production company; representing the players on the ATP Board; and promoting a new tennis event that he hopes will find a permanent time slot on the professional tour.

Call it Gimelstob Industries…an ever-expanding empire that shows no signs of slowing down.

Tour veteran Mardy Fish isn’t at all surprised at his good friend’s success. “He’s extremely quick-witted and is passionate about tennis. His knowledge of the sport is unparalleled.”

Veteran tennis reporter Matt Cronin agrees. “Justin was always full of life as a player, so I did expect that he would try his hand as broadcaster, but what I did not anticipate was that he would be so good in between the lines. He not only is a keen strategist who can explain the ebbs and flows of a match, but he also is very good technically when explaining various strokes.”

“To a certain extent it was calculated,” Gimelstob said, reflecting on the direction of his second career. “I always knew my tennis would come to an end, and I didn’t want to be that guy who had nothing to jump to. I’ve always been comfortable around people, comfortable speaking in front of a crowd. Broadcasting seemed like a natural next step for me. I’ve just been lucky that I’ve been given some great opportunities, and I’ve tried to make the most of them.”

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The Hardest Working Man in Tennis

The Hardest Working Man in Tennis

Gimelstob has made a habit of getting himself noticed. As a kid, he won three national titles (including Kalamazoo, one of the most prestigious events), and he finished the year as the top-ranked junior in the country twice, once in the 14s, once in the 16s. As a freshman in college, he led UCLA to the team finals (losing to Stanford) while also winning the NCAA doubles championship. And in the pros, Gimelstob reached a career-high ranking of No. 63 in singles and No. 18 in doubles. He also won the Australian Open and French Open mixed doubles championships with Venus Williams.

Blessed with boundless energy, Gimelstob is fond of telling people “my only regret in life is that there’s only 24 hours in a day.”

“What amazes me about Justin is that in a relatively short period of time he has become a major power broker in tennis,” said Cronin, who has covered the sport for over 20 years, including for TENNIS.com. “And in many ways, as an ATP Board member who represents the players, he has become the public face of the tour.”

Elected to the ATP Board as a player representative in 2008, Gimelstob has been immersed in tour issues both large and small. Not only does this give him an in-depth understanding of the business side of the tour, but it has also gained him an enormous amount of respect from the tour’s players, both past and present.

“Justin is very popular within the player community, and we rely on him all the time for facts and information about tournaments and rules,” Fish said. “He has the players’ very best interests at heart.”

And if there isn’t already enough on his plate, Gimelstob is now venturing into the world of tournament promotion.

“After the summer men’s tournament at UCLA was sold (and moved to Colombia), Mardy and I got to talking about how we could keep professional tennis in Los Angeles. There’s too much history here. It’s too much of a tennis town to not have a tournament. So, what could we build to take its place?”

The Los Angeles Tennis Challenge (www.latennischallenge.com) is the result, an exhibition featuring a star-studded list of players, including top ranked Novak Djokovic, Pete Sampras, the Bryan brothers, and Fish.

The prior Los Angeles tournament withered on the vine, the result of sponsorship troubles and a poor spot on the summer tour calendar. This event, Gimelstob believes, has the potential to grow into a small but important tournament that leads right into the BNP Paribas Open at Indian Wells. The Los Angeles Tennis Challenge, played indoors at the refurbished Pauley Pavilion on the UCLA campus, has signed a three-year deal with university, and will expand to two days in 2014, involving both men and women.

Sports broadcasting is overflowing with men and women like Gimelstob, professional athletes with mediocre or shortened careers who then went on to excel at broadcasting. But Gimelstob always seems to be thinking bigger, always seems to be looking ahead. When asked who he has modeled his career after, the answer may come as a surprise: Mary Carillo.

“We both had a comparable playing career,” he said. (Carillo had reached a career-high singles ranking of No. 33, and was also forced to retire early due to injuries.) “After retiring, she moved into some television work, commentating, doing analysis. But she kept striving for more. Now she’s recognized as a legitimate journalist. She does the Grand Slams, she’s a regular on HBO Real Sports. Mary has crossed over from tennis-only into something more.”

Gimelstob logged almost 155,000 air miles in 2012, and spent 236 nights in hotels. While this may have been the price required to keep the Gimelstob empire growing, it took a toll physically.

“That kind of schedule is unsustainable over the long-term. I just can’t keep it up,” he said. “But it all comes from an issue I have with saying no. It’s the toughest thing for me to do. People come to me with something, I always want to say yes. I don’t want to leave anything on the table, I don’t want to miss an opportunity.”

So far, his 2013 is following the same frenetic pace. Gimelstob has covered tournaments in Auckland, Melbourne, San Jose, and Memphis, blitzed down to Chile for a Welcome-Back-to-Tennis Rafael Nadal interview, appeared on the television show “CSI”  with Lindsey Davenport and Chris Evert, produced new content for the World of Tennis show on the Tennis Channel, and worked on getting the Los Angeles Tennis Challenge off the ground.

It’s not even March.

Cronin marvels at the stamina, wondering when the guy ever sleeps. “He’s arguably the hardest working man in tennis.”

And Gimelstob wouldn’t have it any other way.