"They’re not good at this": Bill Simmons warns Tom Brady’s role with Raiders could be ‘Dangerous’ for the franchise’s future

Amid the process of NFL picking, the Los Angeles Raiders are making preparations to be in an important place: Green Bay and steer the ship by none other than Tom Brady. This "seven-time" world-beater will be the major factor in securing a good franchise quarterback to the club. An enthusiast for Brady like Bill Simmons gets excited by all this, but even he is concerned about Brady's role in the franchise.

The Las Vegas Raiders' decision to bring Tom Brady on board as a minority owner has sparked immense excitement among fans. The move, approved by the league in October 2024, not only connects the franchise to a seven-time Super Bowl champion but also fuels speculation about Brady’s potential influence in shaping the team’s future—especially when it comes to finding their next franchise quarterback. However, while many are thrilled about his involvement, not everyone is convinced that Brady’s greatness on the field will translate to success in the front office.
Media personality and longtime New England Patriots fan Bill Simmons has raised concerns about Brady’s ability to evaluate quarterbacks. As reported by Awful Announcing, Simmons addressed the topic on The Bill Simmons Podcast, pointing out that legendary players don’t always make great decision-makers.

“This is a dangerous thing where you have him running a football team thinking he knows what’s best with quarterbacks because he was a great quarterback,” Simmons remarked. He further emphasized that history has shown how former elite players often struggle in management roles. “Because all of the evidence with the great players we’ve had, name the sport, mostly they’re not good at this. They think they’re seeing things that other people don’t see, and it’s not actually rational.”
Simmons’ concerns stem from a common issue in professional sports: the assumption that elite players naturally excel at talent evaluation. Many former greats have struggled when transitioning to front-office roles, with John Elway’s tenure as the Denver Broncos’ general manager serving as a prime example.
One of the biggest questions surrounding Brady’s involvement with the Raiders is how much influence he will have on their quarterback selection in the 2025 NFL Draft. With Las Vegas potentially looking for a long-term solution at the position, having Brady’s input might seem like a huge advantage. However, Simmons argues that his presence in the decision-making room could create complications.
“I’m just saying it’s not a slam dunk. Part of the problem is if you and I are in that room with Tom Brady and we were like, ‘yo man, we think Darnold, look…’ and he’s like, ‘I’m out. I watched that game and he doesn’t have it, I’m out,’” Simmons said. “Are we gonna argue with Tom Brady? It’s just now — it’s this one voice that sees what he wants to see.”
This raises a critical point: Will Brady’s opinions be too influential, even if they aren’t always correct? His unmatched playing experience could give him valuable insight, but it also comes with the risk of bias—seeing the game through the lens of his own greatness rather than an objective evaluator.
Brady’s presence in the Raiders’ ownership group guarantees that all eyes will be on the team’s quarterback decisions moving forward. His involvement could be a game-changer if he successfully helps the franchise land its next star signal-caller. But as Simmons pointed out, history suggests that not all legendary players thrive in this kind of role.
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While some may take pleasure in seeing if Brady struggles in his new position, the NFL will ultimately determine whether his transition from the field to the front office is a success. Whether his impact leads to triumph or proves to be a cautionary tale remains to be seen, but one thing is certain—his influence on the Raiders is just beginning.