Who is Jeffrey Kessler? Lawyer who represented Tom Brady is now handling Deshaun Watson case

Jeffrey Kessler lawyer for Tom Brady during deflategate Image Source: sfchronicle.com
Jeffrey Kessler lawyer for Tom Brady during deflategate Image Source: sfchronicle.com

Deshaun Watson and Tom Brady do not have much in common other than that both star quarterbacks played in the AFC. Now, with the NFL investigating the allegations of sexual misconduct/harassment against Watson, the lawyer representing him is the same person who represented Brady. It was back when Brady went through the “Deflategate” scandal from 2014.

Jeffrey Kessler studied law at Columbia University and is a partner at the law firm Winston & Strawn. He is the premier attorney for sports law practices and just mentioning his name around the NFL seems to elicit different responses. Of all the the responses, they have a common theme: Kessler is great at his job.

Players think that Kessler keeps the NFL commissioner in check, league officials think Kessler is “undermining the game” and “ruining it." While coaches love Kessler because he “gets players back on the field.” Perhaps the best way to describe Kessler is what one league official said, “[Kessler] scares me because he’s so good.”

Kessler is most notable for bringing free agency to the NFL in the mid ‘90s. He is also known for successfully arguing in front of the U.S. Supreme Court in the NCAA antitrust case. It alleged that the NCAA violated antitrust laws by putting into place strict limits on how much college athletes can earn in compensation.


Although Kessler represented Tom Brady during the Deflategate scandal, the NFL suspended him for four games in the 2016 season.This was after he already appealed the suspension and was able to play the entirety of the 2015 season.

The NFL is seeking a significant suspension for Deshaun Watson

According to reports, the NFL is looking to make an example of Deshaun Watson for the allegations of sexual misconduct and harassment that resulted in 24 total civil cases. Watson has settled 20 of those cases, but the league is looking to discipline him under its conduct policy.

Watson, Kessler, and the NFLPA will reportedly counter. Their strategy will be why team owners like Daniel Snyder (Washington Commanders), Robert Kraft (New England Patriots), and Jerry Jones (Dallas Cowboys) were also not suspended. They're claiming it's similar to Watson's case for allegations of off-field incidents related to sexual harassment or misconduct.


The Cleveland Browns will have to wait while the league conducts its investigation before the team knows when or if Deshaun Watson will be available to play this season.

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Edited by James Meyers