Chris Evert knows what it’s like to be at the top of the tennis world as a player, but since retiring, she’s gotten to experience some of the sport’s most exciting moments from the broadcasting booth. 

One of the most memorable came at last year’s US Open in New York when she and ESPN colleague Chris Fowler were joined by NBA great Kobe Bryant. “I was fascinated by how mentally strong and how mentally attuned he was to tennis and comparing it to basketball,” Evert says. “It was really thrilling to do a match with him.” Bryant, a former Los Angeles Lakers superstar, died in a helicopter crash in January in Southern California. 

Evert, an 18-time Grand Slam singles winner, is part of a group of former players from around the globe, including Pam Shriver, Sam Smith and Daniela Hantuchova, to transition from player to broadcaster.

After years of fierce competition, players who move into commentating often replace their rivalry with camaraderie. Shriver says one aspect of broadcasting she enjoys is working with longtime friends such as Evert. “One of the things that’s fun is when you stand the test of time with somebody, like Chrissie and I do,” Shriver says. “I think it really helps when you’re working alongside somebody who’s a friend and somebody who you’ve been through life situations with.” 

Shriver says she and Evert appreciate each other’s humor, though not everyone understands their friendly banter. “Sometimes people think we’re being mean, but we’re actually just needling each other,” says Shriver, a Maryland native and former World No.3. “It’s funny, because I feel like guys can do it without a problem, but sometimes when two women do it, it’s interpreted differently.” 

Evert says she likes being on-air with Shriver not only because they’re friends but also because it’s good for women’s tennis.“She’s the only woman on our roster that’s play-by-play, so it makes for a fun match because I can talk to her about women’s tennis in our day,” Evert says. “I can’t really do that as much with the guys, even though the guys are great.”

Going from playing the game to analyzing it is not easy, but former British No.1 Sam Smith got a leg up, literally. About a week after major ankle surgery, Smith accepted a job commentating in London, and she now jokes that she must have still had anesthesia coursing through her veins when she agreed to it. She decided to give it a shot while rehabbing but had no plans of commentating long-term.

On her first day, she showed up at the studio on crutches with a thick plaster cast on her leg. She credits former Eurosport colleague Chris Bradnam with helping her through it. “They had to construct a massive box of cushions, and I sat there with my foot up,” she says. “I was like totally spinning with all the drugs in me and pain, and Chris was very attentive. He was so protective and fatherly, and it was a great experience. It’s like your first tennis lesson. If it’s not a good experience, you won’t want to do it again.”

Like Smith, Hantuchova decided to give broadcasting a try and credits a colleague with helping her to make a smooth transition. “It came kind of naturally because the day I announced my retirement at Wimbledon was the first day of this new job,” says the Slovak former World No.5. “I just wanted to try it out, and I was very lucky to work with Jason de la Peña at Fox Sports Asia. We clicked right away, and I enjoyed it so much that I’ve never looked back.”

While Hantuchova started commentating the day she retired in 2017, Shriver started in her third year on tour. She was just 19 when she joined the ranks of women such as Virginia Wade and Billie Jean King as a guest commentator on CBS in 1981. Shriver continued as a part-time broadcaster for several networks while still playing.

Evert first tried her hand at commentating in 1990, not long after retiring, but she didn’t feel comfortable with it then, she says. “I had trouble kind of articulating and observing all of the different patterns and all the different techniques and everything that was happening on the court because I played by instinct, and I really didn’t think a lot when I played,” Evert said.

Evert took nearly a 15-year break from the booth, had children and opened Evert Tennis Academy in Boca Raton, Florida, with her brother, John. During that time, techniques, rackets and styles changed, but Evert kept up with the changes by working with players at her academy. “I learned a lot about the game from the coaches at my academy and from the players that we trained who came in and out of the academy,” she says. “I felt like I was more knowledgeable of the game at that time, and it was a totally different game.”

Something else had changed about the game in 15 years: a new generation of players had come of age. “Before, I was commentating matches where my friends were playing, and I was a little too close to those players to have constructive criticism and not be afraid to say what I felt,” Evert says. “Now, the players are three generations after me, and I feel that I can have a little more clarity and have constructive criticism.”

Sometimes, for even the most experienced commentators, things on the other side of the microphone don’t always go as planned. Smith says she remembers an incident that happened when covering the women’s 2019 Australian Open final for Australia’s Channel 9. She was about to go live from a small, dark, court-level bunker with colleagues Jim Courier and Alicia Molik. The three were facing the court, but to look into the television camera for a planned pregame segment, they had to spin their chairs around. After several spins because of false starts and the shot ultimately being canceled last minute, Smith’s headset cable became wrapped around the leg of the chair and came off her head. With lights off in the tiny broadcasting bunker, and with the show starting in 20 seconds, panic set in.

“I looked at Jim, and he could see there was no way I could get us on air by the count,” Smith recalls. “So Alicia gets her phone out and shines the torch, and we are literally coming into the final and the two of us are on the floor, under the chair. We can’t see what we’re doing, trying to get the cable unwound from the chair. We’re crying with laughter.”

Courier had to pick up the commentary as the players walked out on court. At the time, Channel 9 had no idea there were any problems in the booth. Smith says the three of them still laugh about the experience.

Sam Smith working at the 2011 US Open.

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Laughing seems to be a common occurrence among commentators. Hantuchova recalled a time late last year when even repeated mistakes turned into a fun moment. “In the fall, we were trying to make some takes, and we were not even going live,” she says. “It was pre-recorded, and we had the usual bloopers, but when you’re trying to say something for the 20th time, the same thing, it gets really funny. I would say once the cameras are off and you’re joking around with the team, that’s a really cool part of the job.”

Even a hair-and-makeup session can turn into a comedy show. Evert recalled a time when she, Lindsay Davenport, Martina Navratilova and others were preparing for a tournament. “Sometimes, it’s like party time when we get into hair and makeup,” she says. “It’s Lindsay and Mary Carillo and Martina and myself and Pam. It can get loud and rowdy, and the makeup girls are all over the place, and we, as players, are giving advice like, ‘Martina, you’ve got too much blush on’ and, ‘Martina, do not wear that color lipstick.’ We’re on each other, and it’s fun.”

Evert says it also is fun to be on the air with former tennis star John McEnroe. “I’m always on my toes with him,” she says. “We have a lot of fun when we’re doing a match. He brings out the naughtiness in me on TV, which is good. I probably say a little bit more with him than I would with any other commentator.”

Shriver says the morning planning meetings can be fun and would be entertaining if edited into a 'best of' video. “There are funny moments, but it can be tough, too,” Shriver said. “Sometimes you’ve had a long day and you’re assigned a late match, which becomes an even later match because the match before you ended up going five sets, and you’re fighting a bit of jetlag and you end up going on the air around 11pm local time. It’s exhausting, but it’s also invigorating. You just keep going because the adrenaline and the energy just take you along. Sometimes you don’t realize how draining it’s been until it’s over.”

A commentator’s day can consist of matches starting at 11am and ending past midnight at 2am. “There’s a lot of hurry-up-and-wait,” Evert said. “We’ll be on site for 12 hours. We’ll have a match and then we might have five hours where we’re not doing anything, and we’ll have another match. It’s just completely different than being a professional where you play your match and then get out of there.”

Hantuchova said the long hours are the biggest challenge with the job. “Obviously, the physical part of playing matches is much more demanding, but the hours, as far as how long we have to be on site, are much tougher now,” Hantuchova said. “But it’s such a wonderful job, and I think getting to be a part of tennis in a different way and understanding much more about the nature of our sport is exciting. I feel I’m learning something every single day.”

Daniela Hantuchova in the studio alongside Greg Rusedski before the 2018 US Open.

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The benefits of the job more than make up for the long days, according to Shriver.  “I love seeing tennis history being written, and there’s been a lot of it in recent years,” she says. “I like seeing how the tennis players handle the biggest matches.”

Evert agrees that what broadcasters get to witness is something special. “We’re getting a bird’s-eye view. We’re in on their happiness, and it’s a very personal, very intimate moment that we are privy to,” Evert says. “I feel very lucky and very privileged that I get to be front and center, and try to tell the story of what’s unfolding in front of us during four of the biggest tournaments in the world.”

Job perks like that have made commentating a highly sought-after occupation for former players. It’s been nearly two decades since Smith’s first broadcasting experience while wearing the thick plaster cast. Today, she is the veteran broadcaster, helping up-and-comers. “I’ve worked a lot over the last few years with newer experts who are doing it for the first time, and it’s very important,” Smith said. “I want to give them the experience I had. I want to be very protective of them and build their confidence.”

She also has some advice for those wanting to make the career switch. Smith said many people think going into broadcasting is a planned move, but there isn't a linear path to it. “It can be quite spontaneous,” Smith said. “Because you’re an athlete, you’re used to steps and a path, and it does not work like that at all - so don’t be frustrated if it doesn’t.”

With such high-achieving athletes moving from making the shots to calling them, Evert said the commentary field is strong. “It’s an attractive job,” she said. “The standard is very high right now. There’s a little competition, but it’s good competition. We’re pushing each other to become better and better.”

Watch now: Tennis United Episode 11