Tom Brady owns a piece of the Las Vegas Raiders today, but according to team owner Mark Davis, the quarterback almost suited up for them five years earlier. In a recent in-house interview published by the Raiders, Davis admitted he still feels lingering regret about missing the opportunity to sign Brady as a free agent in 2020.
“He was supposed to be here in 2020,” Davis said. “That’s when our relationship started, was in 2020 when he was a free agent and we talked to him about coming here to play quarterback. Obviously, it was a tough decision, he was close to coming here, but the head coach and general manager decided they wanted to go in a different direction. So, we didn’t sign him, but as I got to know him through that process, I let his agent know that when he was done playing, I would like him to be a part of our organization.”
At the time, that decision belonged to then-head coach Jon Gruden and general manager Mike Mayock. Both stood by Derek Carr, leaving Brady to choose Tampa Bay instead. In hindsight, Davis concedes he has “some bad feelings” about how it all played out.
A Different Path for Brady and the Raiders
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Brady had just left New England after two decades and six Super Bowl wins. At 43, questions surrounded how much he had left in the tank. The Buccaneers bet big, and it paid off immediately: Brady delivered a Super Bowl in his first season in Tampa, his seventh and final championship ring.
The Raiders, meanwhile, finished 8–8 in 2020 with a top-10 offense but a defense that surrendered more than 30 points in 10 games. Even with Brady, it’s debatable whether Las Vegas could have matched Tampa Bay’s success given the structural flaws elsewhere on the roster.
Former tight end Darren Waller said in 2023 that “Brady to the Raiders was a lock,” a sentiment echoed by UFC president Dana White, who claimed he worked behind the scenes to broker a Brady–Rob Gronkowski package deal to Las Vegas before Gruden pulled the plug.
Ownership, Broadcasting, and NFL Rules
Though Brady never wore silver and black on the field, he eventually joined the organization in the boardroom. Davis later sold him a minority stake in the team, though the process was far from straightforward.
“It wasn’t an easy process, but the National Football League eventually let it happen,” Davis said. “Now, in fact, the other day, they changed the rule on him and he’s allowed now to talk to players.”
That rule change relates to Brady’s other role as Fox Sports’ lead NFL analyst. The league needed to clarify the boundaries of what a minority owner with a broadcasting job could and couldn’t do, given concerns about conflicts of interest.
What Might Have Been
Looking back, it’s fair to wonder how NFL history might have changed. Had Davis overruled his football operations staff and signed Brady in 2020, Las Vegas might have been the stage for his final chapters rather than Tampa Bay. Instead, the Raiders endured middling seasons, Gruden resigned in disgrace a year later, and Brady added another Lombardi Trophy elsewhere.
For Davis, the sting remains. Brady may be a Raider now in an ownership capacity, but as the owner himself said, “He was supposed to be here in 2020.”