Raiders owner Tom Brady has had growing pains early as executive

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Tom Brady has gotten a lot of attention for sitting in the coach's booth for the Las Vegas Raiders Monday Night Football game against the Los Angeles Chargers.
We'll let others debate the merit of whether the NFL QB GOAT is getting an unfair advantage as a Raiders minority owner while also being FOX Sports' $375 million No. 1 NFL analyst, but so far, the wannabe motivational speaker and writer has proven he's not a very good executive.
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How, you say?
There is no doubt that Brady was a leader as a teammate, winning an unprecedented seven Super Bowls for the New England Patriots and Tampa Bay Buccaneers, which is a record that will probably never be matched.
But being the GOAT as a player doesn't translate into being a GOAT executive, and if you closely watched Amazon Prime's five-episode docuseries, "Built in Birmingham: Brady & the Blues," the 48-year-old has already shown that he's a terrible owner, at least so far.
No self-awareness and completely arrogant

Brady, who amazingly was one of the executive producers trying to recreate the magic of "Welcome to Wrexham," which means he probably had final approval of what was shown, is completely arrogant taking over Birmingham City FC, a storied club that is currently playing one level below the prestigious, and extremely lucrative, English Premier League.
Brady's buddy, financier Tom Wagner, is the majority owner, and he seems to be the true brains behind the operations. Brady is supposed to bring the charm, but it falls flat. Very flat.
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Wayne Rooney meets Tom Brady in a scene which feels like it has been filmed by the makers of The Office. Truly incredible cinema 🍿
— Men in Blazers (@MenInBlazers) August 1, 2025
📹 @primevideosport pic.twitter.com/tFnF3XE0c6
There are countless examples, with the Wayne Rooney take down that went viral being one of them, but two more that stand out are him criticizing the team from the warmth of a fancy Miami beach while the team suffers through the brutal winter stretch, and joking to the local Birmingham driver when he flies in, on a private jet, to scold more people in the organization with his equally arrogant manager, as they make fun of the way to say "Birmingham."
Started watching ‘Built in Birmingham’ and, so far, Tom Brady’s arrogance is excruciating. If he was an ice cream he’d eat himself. pic.twitter.com/jgZZ4Axf0N
— Ray Armfield (@KentWomble) September 11, 2025
"Honestly you guys need to come up with a name for me that is just going to show your respect," Brady said. "Like your highness or my savior. Anyone of those will suffice."
Eww.
Brady wants to be bigger than Wrexham, but he has none of the charm

Both Brady and Wagner belittle Wrexham AFC throughout the series, saying Birmingham should become a bigger global phenomenon. Yet, neither have the Wrexham charm.
Brady says, “What’s different in soccer than football. Nothing.” Umm, wrong.
After getting demoted in their first season as owners, firing two managers, Brady can't blame himself, so of course it's someone else's fault.
🚨 | After sacking Wayne Rooney, Birmingham owner Tom Brady wanted Ted Lasso to be the next manager until staff informed him that Ted Lasso is a fictional character. ❌
— Just Bizarre Tactics (@JBTFooty) August 8, 2025
(via @SkySportPL) pic.twitter.com/gsaGsaXLrA
"We’re trying to make this a world class team," Brady said. "But the reality is, it’s been a shit year. What’s the problem. It’s the players or the coach. Well, we already changed the coach. It’s really the players, because the coach doesn’t go out there and put the ball in the goal. They were lazy. They were entitled. And when you’re lazy and entitled, you don’t have much of a chance to really succeed."
Great leadership!
Raiders fans should be scared

Rob Mac, formerly Rob McElhenney, who is the true magician, along with Ryan Reynolds, in making Wrexham AFC that global phenomenon that irks Brady and Wagner so much, has the ultimate burn when the two teams face-off in the series.
Talking to Wagner, Mac tells him, "He has all of these ideas about how to talk to players… And I’m like, that’s what Ryan and I stay out of. I mean, we go to the locker room, we say hi, but we stay off… Stay off the pitch. Let the football guys do the football stuff. We do the marketing.”

These same issues will be the problem with the Raiders. He's too meddlesome and doesn't have the same aura as an executive that he did as a player.
The best NFL owners stay out of the way and trust the football people to make football decisions. Brady thinks being the NFL QB GOAT makes him a great evaluator of talent. That rarely, if ever, translates. The Raiders new general manager, John Spytek, is another Brady buddy.
So while fans freak out about getting an unfair advantage, Brady first has to prove he can actually become a good executive. So far, it's not off to a good start.

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Matthew Graham has over 20 years of media experience and oversees The Athlete Lifestyle On SI. He has had previous leadership roles at NBC Sports, Yahoo, and USA TODAY, where he co-founded For The Win (named Best Mobile Site by Digiday). He has also written for ESPN, Cosmopolitan, US Weekly, People, E! Online, and FHM, covering major sports and entertainment events like the Oscars, the Golden Globes, NBA Finals, Super Bowl, and winning the Yahoo Superstar Award for coverage of the Olympics.