The Kid Wants How Much??

The four-month negotiation process was like a tennis match: players on each side edging closer to each other while hitting the ball back and forth over the net. But then, the ball no longer mattered, and both sides met at the net to shake hands. In this case, the two sides were the sports agent Jason Bernstein, A02, and the San Francisco 49ers. In early 2014, Bernstein finessed a six-year, $126 million contract extension for Colin Kaepernick, the star quarterback who had led the 49ers to the National Football Conference Championship in the previous two seasons.

Kaepernick is one of more than two dozen football players represented by Bernstein, who co-owns XAM Sports and Entertainment with Scott Smith and who recently launched his own firm, Clarity Sports International. When Bernstein isn’t hammering out contracts with tough-talking executives or finding his clients product endorsements, he’s navigating around nosy sports bloggers who think they’re the next Bob Woodward, and scouting the next round of collegiate athletes who will be entering the NFL draft and looking for representation.

On any given Saturday during football season, he might be at a college stadium checking out players, or glued to a TV screen, flipping back and forth between channels. Then, on Sunday, perhaps he’ll fly to some NFL team’s arena to meet with a current client. Later in the week, back in the office, he’ll work the phones for clients negotiating endorsement spots (Kaepernick, for example, is in commercials for Jaguar and EA Sports Madden, the Xbox football game), and set meetings with NFL-worthy college prospects.

“Recruiting prospects is a one-to-two-year process,” Bernstein says. “We’ve built relationships with NFL scouts, who give us an idea of who they feel the top players are. Then we meet with the potential prospects and their families to make sure they’re a good fit for us from a character standpoint.”

Under NCAA and NFL Players Association (NFLPA) regulations, agents can talk to athletes while they’re in school, but can’t give them anything of value. Nor are athletes allowed to sign a contract with an agent before leaving school. Unfortunately, Bernstein says, not all agents play by the rules. “Violations occur a lot more than the public might be aware of,” he says. “But we believe it’s most important to do things the right way.”

Doing the right thing is what landed Kaepernick as a client in 2011. “When we signed Colin, he and his family had heard from more than a hundred different agents,” he says. “If you ask Colin and his family why he chose to sign with us, I think they’d tell you that our professionalism and comfort level carried the day—much more so than our client list.”

Negotiating contracts doesn’t generally involve the kind of desk pounding by team owners that you see in the movies, he says. But that’s not to say he hasn’t had contentious parleys. Bernstein declines to name the executives who have growled at him in anger or given him steely looks after hearing a client’s desired contract salary. “I have to work with these people,” he says with a laugh. “But the negotiation process can be stressful at times.”

Bernstein, a lifelong sports fan (his father, Bruce, A73, played basketball for the Jumbos under coach Tom Penders), knew he wanted to be a lawyer and a sports agent while in high school. Sensing how tough the industry would be to break into, he earned a degree in computer science as a fallback.

He also interned for Robert Caporale, A62, co-owner of Game Plan LLC, a sports services and event management company. “In the fifteen-plus years we’ve been in business, I’ve only accepted two interns, and Jason was one of them,” Caporale remembers. “He was anxious to learn the business, and was always asking what he could do. He learned by watching and listening. Our office doors were always open, so he could see who and what we were involved with, and hear what we talked about.”

While Bernstein was studying law at Vanderbilt University, he met Smith, an attorney who was also interested in the sports agent field. They went into business together after Bernstein signed his first player. “My first client,” Bernstein says, “was a kicker named Jesse Ohliger in 2004, my first year as an NFLPA-certified contract advisor. I developed a friendship with him while I was at Vanderbilt. He knew I was an agent, so when he had an opportunity to sign with an NFL club, he called me to represent him.” Ohliger played for the Baltimore Ravens in 2005, and is now a director at One on One Kicking, a kicking/punting school in Florida.

When he’s not watching his clients or recruits play games, Bernstein might relax with a movie—anything except Jerry Maguire, the Tom Cruise flick about sports agents. “It tends to stress me out because it so accurately portrays the cutthroat part of the business.”

This story originally appeared in the Summer 2015 issue of Tufts Magazine.