You Had Me at Hello

Meet Gary Leibowitz, who runs a one-stop agent-and-lawyer shop for athlete clients

Published in 2019 Maryland Super Lawyers magazine

By Matt Amis on December 11, 2018


In 2016, Don Jackson, an undrafted rookie running back, eked his way onto the Packers’ practice squad. 

But his chances of cracking the lineup were slim. He was Green Bay’s fourth option in the backfield. Then, six weeks into the season, the Packers’ top two running backs went down with injuries. 

Jackson’s agent—lawyer Gary Leibowitz—got the call. The next day he flew out and met Jackson at historic Lambeau Field. Agent and player embraced on the sidelines before Jackson made his NFL debut on a nationally broadcast Thursday night game. 

“Just being on the field with him for that moment,” Leibowitz says, “it sent chills up and down my spine.”

It’s just one of many moments in the occasionally glamorous world of sports agency, one that Leibowitz inhabits as both a solo agent to players and coaches, and as the quarterback of the Cole Schotz sports law team. A corporate restructuring and bankruptcy attorney by trade, Leibowitz also acts as an NFL agent, shepherding young athletes from the end of their collegiate careers through the tenuous initial stages of the pros. 

Among the thousands of elite athletes who vie for a spot on an NFL roster each year, only a handful make the cut. 

Unless you’re a blue-chip prospect, the process can be grueling. “You’re dealing with injuries; with players who are lower-round picks or undrafted free agents, who are constantly being cut; going to new workouts and trying to make teams,” Leibowitz says. “You’re always on the bubble.”

Leibowitz also helps clients navigate the game’s mercilessness. In his debut, Jackson carried the ball twice before injuring his wrist. Four weeks later, he landed on the injured reserve list. The following spring, the Packers cut Jackson. 

“Players believe they will play forever, yet everybody is one knee injury from never playing again,” Leibowitz says. “It’s like you and I buying life insurance. Nobody wants to face their own mortality and players don’t want to face the probability of injury. It’s part of the agent’s job to watch those things that the player doesn’t want to focus on.”

A sports guy from a sports family, Leibowitz landed a dream gig in 2005 as outside counsel for the Washington Nationals. It earned him access into the Sports Lawyers Association and greater visibility in pro sports circles. 

“I figured if I was ever going to be more involved in the sports world, now was the time,” says Leibowitz, who began zeroing in on athletes like Jackson: players on the fringe. He also landed a collegiate basketball head coaching job for former University of Maryland and Washington Wizards great Juan Dixon at Coppin State University. 

As demand for Leibowitz’s services grew, he folded them into a newly formed sports law team at Cole Schotz, which could offer a wide menu of support any young athlete might need. 

“We have a very deep bench,” Leibowitz says. When an athlete signs on with Leibowitz as his agent, he’s also handed the keys to a one-stop legal shop, where, beyond simple contract negotiation and endorsement deals, he gets add-ons ranging from trust and estate advice to taxes, merchandizing, and so on. “It allows them to have a very tight circle of trusted professionals,” Leibowitz says. “Nothing will fall by the wayside.” 

It’s an uncommon model, but Leibowitz and the firm help fill a dire need. Pro sports carry a sad history of chewing up and spitting out athletes. Beyond crippling injuries and relentless schedules, an unexperienced millionaire can become easy prey for financial parasites and con artists.

Hall of Famers Terrell Owens and Dan Marino have gone broke after their careers. This summer, NFL linebacker Mychal Kendricks pleaded guilty to involvement in an inside-trading scheme. 

“We put an emphasis on making sure the players and their families will reap the benefits of this violent and difficult, short career so that they are set up financially,” Leibowitz says. “The goal for these athletes is not to make a lot of money in the NFL. The goal is to keep that money afterward because, more likely than not, their careers are going to be short.”

But he says moments like the one he shared with Jackson are pure sports magic. 

“Seeing their smile when they come out of the tunnel with the uniform on for the first time, and realizing that you helped make their lifelong dream come true … that’s much more important than any glamour and glitz to me.”

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