When Old is Better Than New

General Counsel Sashi Brown left one of the newest teams in the NFL—the Jacksonville Jaguars—for one of the oldest: the Cleveland Browns. Here’s why.

By Jennifer Hopfinger

The Cleveland Browns are one of the most storied teams in the National Football League (NFL). Along with the San Francisco 49ers and the Baltimore Colts, the Browns were one of the original members of the NFL. It is the team of Running Back Jim Brown, widely considered to be one of the greatest professional athletes of all time. It is a team with eight league championships and 16 former players/coaches enshrined in the Pro Football Hall of Fame. These days, the Browns are a turnaround story, and Sashi Brown simply had to be a part of it.

A year ago, Brown left his post as General Counsel of the Jacksonville Jaguars (one of the youngest teams in the NFL, where he worked for eight seasons) to join the Cleveland Browns (one of the oldest teams), serving in the same role.

“There are great fans in Jacksonville, but there’s more of a legacy in Cleveland,” Brown said. “There’s more depth to the passion.”

Know & Pave Your Path

Brown may love sports, but sports are not his first love, and it’s not why he got into law. He cautions other young lawyers to think similarly.

“You see a lot of students attracted to law school and sports law programs because they think a law degree is going to provide them an entry into a career in sports, and the reality is there are simply not enough jobs for everyone who is trying to do that,” Brown said. Rather, he advises that aspiring lawyers “be true to themselves about whether they want to be a lawyer or they want to be in sports.”

“I wish I could say I had a plan at the beginning of my career, but more than anything, when I finished school [Harvard Law] in 2002, I was interested in transactional work,” Brown said. “And for me, that meant not going to an enormous firm where I’d be marginalized. I wanted to work on large, sophisticated deals.”

So, he chose Wilmer, Cutler, Pickering, Hale and Dorr, a private law firm in Washington, DC. While the group wasn’t known for transactional work, Brown found it to be a thoughtful place in which to train.

The business side of legal work was appealing to the young professional because, he explained, transactional practice is more proactive and collaborative. He found this to be well suited with his personality, as opposed to litigation, which tends to be reactive and combative.

“I’d rather make a deal than fight over a deal,” Brown said.

The firm also happened to have a sports transactional practice, a rare niche, though there was no promise initially that Brown would be a part of it. Three years later, after expressing interest in and doing work for teams including the Baltimore Ravens, the Jaguars hired him.

Working Under a Microscope, In a Big Lab

Sports teams, Brown conveyed, are small companies with enormous public profiles. “Most of what we do is very public,” he said, “and that creates some interesting challenges. Our deals get reported in the news, so there’s a microscope on our work.”

With all of that scrutiny, what areas does Brown want to improve upon the most?

“Winning cures everything, so the first thing we set out to do is win,” he said. “Then, put ourselves on firm financial ground, create great partnerships and produce great media—we are, in many ways, a media production company. Basically, we want to run a championship franchise on and off the field.”

What’s a typical day for Brown? “I’m waiting for a typical day,” he said. Because it’s a small company, he has to wear many hats in his two-person Legal Department. He could be negotiating a player contract one day and working on risk management insurance the next. “My scope is sometimes uncomfortably broad. There’s no groundhog day for me.”

Jennifer Hopfinger is a freelance writer based in Chicago, Illinois.