Making their names
Editor's note: This story is revised from the print edition.
Talent representation has largely been a male-dominated industry, from contract work to marketing agreements. But that’s begun to change over the years, largely due to the groundbreaking work of the women highlighted below. From an agent handling player contracts in Major League Baseball to executives behind some of the most progressive marketing deals in sports, these five women tell their stories of how they got their start, their first big break and the challenge of working in today’s representation business.
Draft Pix Sports Agency Inc.
Charisse Espinosa-Dash is among the very few women who have become certified player agents in MLB, and she specializes in representing players from the Dominican Republic, including Tampa Bay Rays pitcher Roberto Hernandez and Texas Rangers closer Alexi Ogando.
Espinosa-Dash was born in New York and grew up in New Jersey, but her mother and father were born in the Dominican Republic. Her parents had the resources to travel, and, as a girl Espinosa-Dash watched winter baseball in the Dominican Republic. In the summer, she watched baseball in the old Shea Stadium with her dad, who was a Mets fan.
“I never had a favorite [MLB] team,” Espinosa-Dash said. “I used to cheer on the Dominicans on every team.”
Espinosa-Dash wanted to work in baseball, and her cousin Rafael “Sweet Pea” Deleon, who grew up in the Dominican Republic and was a minor league baseball player and a hitting coach for the Tampa Bay Rays, taught her the business. She started investing in Deleon’s Dominican Republic baseball academy while she studied law at New York Law School, and she signed her first client, outfielder Angel Fermin, when she was 23 and still in law school.
In addition to Hernandez and Ogando, she represents five other minor league players. But it hasn’t been easy, because while she started in 2000, she has lost many player clients, including Carlos Santana, to rival agents along the way. For many, that might have been enough to leave the business.
“I don’t quit,” Espinosa-Dash said. “I’m trailblazing.”
Espinosa-Dash has also helped players from the Dominican Republic with identity and visa issues. She worked for five years to get Ogando and free agent pitcher Omar Beltre back into the U.S. after they were banned in 2005 for being involved in what was reported to be a human trafficking ring. Last July, Espinosa-Dash negotiated a deal with the Cleveland Indians to take back Hernandez, who was formerly known as Fausto Carmona, after he was arrested in the Dominican on identity fraud charges and banned by MLB.
Hernandez was grateful to the Indians and Espinosa-Dash, as he thought he would never be able to return, according to his wife, Yanna Gil.
“She was very persuasive,” Gil said.
Hernandez is pitching this season for the Rays.
Indians general manager Chris Antonetti said, “In my dealings with her, she was always professional in how she communicated and seemed to have a passion for her client and for being an advocate for her client.”
Espinosa-Dash said her biggest challenge in representing MLB players is that she is a woman and other agents use that against her. “A lot of it is, ‘If you haven’t played the sport, you don’t have the knowledge of the sport,’” she said.
In 2011, Espinosa-Dash brought in veteran MLB agent Larry Reynolds to co-represent Ogando to battle “the sharks” in the agent business.
“It’s a boys’ club,” she said. “If you are a woman you have to have a tough skin, and it’s not been a very welcoming industry for women.”
But getting the bans on Ogando and Hernandez lifted has been a turning point for Espinosa-Dash. “It helped me get respect,” she said.
Jill Smoller is, arguably, the pioneer of women sports agents. Since the late 1990s, she has represented high-profile athletes, both men and women, in multiple sports for marketing and entertainment work. Current clients include Kevin Garnett, Serena Williams, Tim Tebow and Olympic gold medal winner Allyson Felix. In the past, she has worked with Rick Fox, Keyshawn Johnson, Pete Sampras, Dennis Rodman and Florence Griffith Joyner.
Smoller is a former pro tennis player, but she didn’t break into the agency business through sports.
In 1996, at 28, after retiring from her brief career in doubles, she arrived in Los Angeles to take a job in the mailroom of Hollywood talent firm ICM, with a starting salary of $200 a week. She was promoted to agent 11 months later. “It was luck in timing,” Smoller said of her career break. “Remember that whole cliché of ‘sports and entertainment’? That’s when that started. It was ’97. There was a show on TV called ‘Arli$$.’”
At ICM, they were looking for athletes to book on HBO’s “Arli$$,” the Robert Wuhl vehicle about a sports agent. Meanwhile, sports agents were looking for a way to get their athlete clients to cross over into television, movies and other forms of entertainment.
Smoller wasn’t and still isn’t certified to represent athletes in playing contract work, but she was able to form alliances with sports agents to get their clients entertainment work. And, through her contacts in tennis, she was able to secure Williams as a client.
Deals have included Kevin Garnett’s multiyear deal with Chinese shoe and apparel brand Anta, Serena and her sister Venus Williams’ deal with Apple, and Tebow’s deal with TiVo.
“For me, being a woman hasn’t mattered, I don’t think,” said Smoller, who acknowledges that to be a woman agent, “you have to have a thick skin and a strong stomach. Athletes don’t want to have to feel they need to watch what they say and watch what they do around you because you are a woman.”
For Smoller, the lowest low in her career came in February 2011, when she comforted Serena Williams in an emergency room after Williams suffered a pulmonary embolism. That day, Smoller didn’t know if Williams would survive, let alone ever play again.
“I believe the mark of a great agent is helping people to navigate through a very difficult, very dark time, and that you are the same person then that you are when they are winning everything,” Smoller said. “It’s easy when everyone is around and everything is fabulous. But when things go wrong, who is there to support you and help pick you up and be part of your team?”
Williams did come back, and in 2012 she won Wimbledon, took two gold medals at the London Olympics and won the U.S. Open.
Today, Smoller says her biggest challenge is balancing a personal life with a demanding career. “Nobody ever tells you it is harder to stay high up in the game than it is to get there,” she said. “You always think the hardest thing is the climb. It’s actually much harder to sustain a successful career.”
Excel Sports Management
Jaymee Messler started her career in sports while in her early 20s, working as an executive assistant. But she steadily worked her way up to take on more responsibility with clients, first handling their public relations, then marketing, to today, where she is negotiating partnerships with global brands for superstar NBA players.
Those who know her say that not only does Messler, Excel Sports senior vice president of marketing, have a natural ability for communicating with athletes and companies, she is an innovator when it comes to endorsement deals.
Blake Griffin’s multiyear global deal with automaker Kia came out of a conversation Messler had with the Los Angeles Clippers power forward about what he thought he might do at the 2011 NBA All-Star Weekend dunk contest. Griffin mentioned to Messler that he was thinking about jumping over a car. Since Kia was a sponsor of the NBA, Messler approached Kia with the idea of Griffin jumping over a Kia Optima.
Then she asked Griffin if he thought he could do it.
“He said, ‘Get the measurements of the car and I’ll let you know,’” Messler recalled. “So Kia sent me the measurements. I think the first time I called them, they thought I was crazy.”
Last year, Messler came up with the idea of creating a “digital magazine” for Brooklyn Nets point guard Deron Williams by hiring his own staff writers to write about him, a concept that was written about by The Wall Street Journal. Recently she was involved in negotiations with Pepsi to put Excel client Kevin Love in the “Uncle Drew” series of webisodes.
Prominent NBA player agent Jeff Schwartz, president of Excel Sports Management, hired Messler 16 years ago to be his personal assistant when he was a tennis agent at IMG. Prior to that, Messler was the assistant to the late, great chef Jean-Louis Palladin, managing all the details of his life.
“I had a twin brother and we both grew up playing sports and watching sports,” said Messler, who played basketball and volleyball in high school. So working in sports was attractive, she said. But she said she also loved managing and being around talent, and she saw the opportunity to work on marketing and branding.
“Jaymee moved up the ladder,” Schwartz said. “I realized early on that Jaymee has a knack with the clients. She understands them. She really does. She understands the intersection between managing a client and marketing a client. And there is an intersection.”
An example of how Messler manages and markets clients is Williams, who joined Excel two years ago. “When he came here, he had Nike, but he really wasn’t a highly marketed athlete,” Schwartz said. “His profile did not fit his level of play on the court.”
Messler took the lead and secured a deal for Williams to write a blog for ESPN from Turkey, where he played during the NBA lockout, as well as creating a “digital hub” for him that included Twitter, Facebook and his own staff writers. Williams now has partnerships with Red Bull, American Express and MetroPCS, and is on the cover of the “NBA Baller Beats” video game.
“That is a great example of repositioning him to the marketplace,” Schwartz said. “Reintroducing him to the market and going out and explaining to them why he makes sense for all these different companies to use, and Jaymee did that.”
In 2011, Excel expanded into baseball and golf when agents Casey Close and Mark Steinberg joined as partners, and Messler’s job duties expanded to include the marketing of MLB players and golfers, as well. Steinberg oversees all the endorsement deals for Excel’s clients, and has been working closely with Messler on strategy and negotiations. She recently negotiated an endorsement deal for PGA Tour player Matt Kuchar with Grey Goose Vodka.
Steinberg credits Messler with a natural approach in dealing with corporations, athletes and advertisers, and marvels at her ability “to play off each other” in meetings.
“I have got to tell you, she is fantastic,” Steinberg said. “She brings an energy and a creative vision I just never had in my prior jobs. I didn’t have that creative go-to person, who was truly like a marketing guru.”
Messler said that opportunities for women are growing in sports, especially in digital media and athlete branding. But it wasn’t always that way.
“In the beginning, I didn’t have that many women who were mentors to me, because there weren’t that many working in the world of sports,” Messler said. “Jeff was one that was a mentor to me because he was able to support me and also empower me to be successful.”
Since joining Creative Artists Agency three years ago as a member of a team of agents representing sports broadcasters, Becky Sendrow has helped negotiate numerous deals for television personalities, including Michelle Beadle and Rich Eisen.
Sendrow grew up the youngest of three sisters and loved sports, in addition to movies and television. She played tennis at Cornell and then got her law degree at Cardozo School of Law at Yeshiva University in New York City. Upon graduating, she was offered high-paying jobs at law firms but chose, instead, to take a low-paying job in the mailroom at what was then the William Morris Agency, in 2005.
“When the opportunity came up to work at William Morris and to potentially work with talent and television and sports, it was too good to pass up,” Sendrow said. While declining to reveal what she was paid when she started out, she adds with a laugh, “I will tell you in order to take this job I lived on a couch for two years.”
But two years later she was promoted to agent at the William Morris Agency and started representing all kinds of on-air talent, including news, sports and lifestyle broadcasters.
In 2010, Sendrow was offered a job at CAA and took it, she said, because of her love of sports and CAA’s growing sports talent representation business. “Really, my goal was to work at a similar, wonderful vast agency with so many assets, but focus on sports,” she said.
At CAA, Sendrow works closely with a number of broadcast agents, including Andy Elkin, Nick Khan and Tom Young, among others. “We really work in teams here,” Sendrow said. “At no point is it me signing [a personality] or one person signing someone, it is really a group effort with our department.”
Sendrow said one of the things she likes about her new job is the opportunity to work with current athletes who are looking to get broadcast experience before they retire, with an eye to a second career in television. She helped Washington Redskins linebacker London Fletcher secure on-air appearances with ESPN, CBS Sports Network and NFL Network in January and February of this year.
“Becky helped me with my career aspirations in broadcasting,” Fletcher said. “She is very knowledgeable.”
The most important thing, Fletcher said, was Sendrow secured “lots of reps” on television as well as introductions to executives at the networks. “Getting in front of the decision-makers is important,” he said.
Sendrow said a challenge she enjoys is helping sports personalities find other work in entertainment projects. CAA represents talent throughout the entertainment industry, including television, motion pictures and music.
NFL Network anchor Eisen said that Sendrow and Elkin helped him get a non-sports reality show that aired on TNT last summer, “The Great Escape.”
“I have frequent contact with her,” Eisen said of Sendrow. “She is always someone who is completely on the ball and someone I have no problem or worry about representing me.”
Elkin and Sendrow also worked closely with Beadle on a deal in which she ultimately moved from ESPN to NBC. At NBC, Beadle is reporting not just on sports, but entertainment as well.
Beadle, in an email, said Sendrow helped her weigh the pros and cons of various opportunities she was offered before she agreed to the NBC deal. “I love having a woman in my corner,” Beadle wrote. “She serves as a great sounding board, and someone who has become well versed in the art of dealing with me. She’s also a bit of a sarcastic character, which goes well on this ride.”
In a male-dominated sports environment, Sendrow said she doesn’t think being a woman has hurt her career. “I have never been treated or looked at as someone who is a female in the industry and thus treated differently,” she said. “I am very supported. But I am very proud to be in this industry as a woman.”
LINDSAY KAGAWA COLAS
Wasserman Media Group
Lindsay Kagawa Colas negotiated the first deal for a female basketball player with Nike’s Jordan Brand and has raised the market for women’s basketball players by negotiating landmark deals for them overseas.
Colas, Wasserman Media Group’s vice president of Olympics and action sports, represents some of the best women’s basketball players in the world, including Maya Moore, the No. 1 pick in the 2011 WNBA draft, and Brittney Griner, who was picked No. 1 overall in this year’s WNBA draft by the Phoenix Mercury.
Wasserman Media Group beat out a lot of major agencies to sign both players, and Colas has the admiration and respect of some of the most powerful agents in sports.
“She is probably one of the best agents I have worked with in my entire career,” said Arn Tellem, Wasserman Media Group’s vice chairman and Colas’ current boss. Tellem frequently used the word “tenacious” to describe Colas. “I don’t think anyone is as committed, and she gets the best results for her clients than any agent I’ve ever run across.”
Colas’ former boss, BDA Sports president and prominent NBA agent Bill Duffy, hired Colas initially as his executive assistant and then promoted her to an agent. He touted her smarts and style.
“She is smart as a whip,” Duffy said. “She is very thorough and very diligent. She is very competent and extremely loyal. She communicates like a dude. I am not saying she is not beautiful and feminine. I am saying she is very aggressive.”
Colas first met Duffy in 2002 when she interviewed him as part of her research for a fellowship at Stanford about how athletes could become more involved in community causes and fundraising. The meeting turned out to be more of a job interview, with Duffy hiring her a few weeks later.
In 2005, Colas overheard Duffy taking a call from someone asking him if he would be interested in representing Diana Taurasi, who was then the WNBA rookie of the year. “I heard Bill say, ‘That’s really not what we do,’” Colas recalled. “I don’t remember if I cut him off or I waved in front of his face but, in the middle of the conversation, I said, ‘I want to do it.’”
After an interview process, Colas began representing Taurasi, who had been a No. 1 draft pick, for marketing and contract work, with Duffy assisting her.
Taurasi said in an email from Russia, where she plays for UMMC Ekaterinburg of the Russian Premier League, that she hit it off with Colas from the start and believes she’s unlike anyone she had met before.
“She looked at things with a different lens,” Taurasi wrote. “A much brighter and broader lens. … Her personal touch is what sets her apart from the rest. And that I can say because I experienced it firsthand.”
With Taurasi in the fold, Colas began to build a women’s basketball practice at BDA Sports, expanding it to represent half a dozen players.
But in 2009, she got an offer to work at Wasserman Media Group to represent not just women’s basketball players, but female athletes in other sports. Over time, she’s signed new clients that have included beach volleyball players Jennifer Kessy and April Ross as well as UConn women’s basketball coach Geno Auriemma.
Colas said one of the hardest things she ever had to do in her career was to tell Duffy, who remains a close friend, that she was leaving. She asked him to a breakfast and broke the news that she was taking the job at Wasserman because, in part, she believed women’s basketball players could benefit from being part of an agency that represented other athletes, especially Olympic athletes.
“I was really nervous,” Colas remembered.
But Duffy took it well. He told her that he wanted what was best for her, which included having a bigger platform to grow at Wasserman. “I really respect Arn and I knew she would be fine there,” Duffy said. “If she was going to the wrong place, I wouldn’t have allowed it to happen.”
Colas says her biggest achievements include negotiating the deal for Moore to become the first female basketball player sponsored by Nike’s prestigious Jordan Brand in 2011 and negotiating playing contracts for women basketball players overseas.
“She really fights for her clients, whether it’s team contracts or endorsement contracts or protecting them,” Tellem said.
Colas said she likes to represent female athletes, like Taurasi, Moore and Griner, believing that such women have the potential “to change how people think about things, about women, opportunity, equality and justice.”
As for being a woman in a male-dominated business, Colas said, “Of course sexism exists.” But Colas made it a point to say she wouldn’t be an agent at all if it weren’t for support from Duffy, Tellem, Steve Astephen (Wasserman Media Group, president action sports and Olympics), as well as Wasserman Chairman and CEO Casey Wasserman.
“If you look around, any woman who has accomplished something, most of us went through a man who gave us the opportunity,” Colas said. “That is certainly the case for me.”