Welcome back to Club Sportico, where we break down the intersection of sports and money—with an extra bit of humor and opinion. Today, we’re talking about a scandalous goat.
Tom Brady retired–”for good” this time–in 2023, but he still manages to stir controversy across the world’s richest sports league.
The latest dust-up came this past weekend, when Brady appeared with a headset in the Las Vegas Raiders’ coaches box during their Monday Night Football game against the Chargers. Brady is an investor in the Raiders and also the lead analyst for Fox Sports’ NFL broadcasts, a combination that many consider a conflict of interest.
During the 2024 season, Brady’s first in the booth, the NFL forbid him from attending practices or participating in the pre-broadcast production meetings, where coaches typically speak candidly about their players’ health and their gameplan. This season, the NFL loosened some of those rules.
He’s either constantly being unfairly victimized as a result of his decades of success, or he’s simply run out of benefit of the doubt—depending on how often you patronize Dunkin’.
That policy change, combined with his appearance in the coaches box, sparked new controversy this week. After the game, Raiders coach Pete Carroll had to clarify that Brady speaks with–but doesn’t ‘meet with’—Raiders coaches throughout the week🤔. An anonymous NFC executive told Yahoo! that “I don’t like the idea of him spending time in our building talking to everyone when we are in gameplan mode... The headset makes all that worse.” The NFL told reporters that Brady had done nothing wrong.
Part of the issue here is that controversies have dogged Brady for the last 25 years. He’s either constantly being unfairly victimized as a result of his decades of success, or he’s simply run out of benefit of the doubt—depending on how often you patronize Dunkin’.
In honor of TB12, here are 12 of Club Sportico’s most enduring Brady miscues, and where the latest fits, ranked by Jacob, Eben, and Lev.
Honorable Mentions:
Pitching Uggs (2011) — not the last Brady endorsement deal to make this list.
Vouching for Antonio Brown (2021) — … twice
“Unretiring” to play flag football in Saudi Arabia (2025) — only Tom’s second biggest controversy this week.
Getting kicked out of a Tampa park that was shut down during COVID (2020)
Looking like a zombie next to Tony Dungy (2021) — as seen in the reddit thread r/oddlyterrifying. It remains unclear if either were wearing Uggs.
And now on to the top 12. Let us know what we missed!
Tom Brady’s 12 biggest scandals
Alex Guerrero has turned a lot of people off over the years, from Bill Belichick to a notable Boston doctor to the FTC. But TB12 has stuck by him. Guerrero is now the “wellness coordinator” for the Oakland Raiders.1
The NFL said the meeting, which came while Brady was reportedly trying to convince Stafford to join the Raiders, didn’t violate league tampering rules. Bonus points for this scandal sparking the Thrilla in Vanilla (Latte) incident.
The newest entry on our list. Brady initially played down his role with the Raiders after acquiring 5% of the team, saying he’d stay behind the scenes. Then he showed up very much on the scene of Monday Night Football, wearing a coach’s headset. Now, others around the league wonder if he could use his access to teams as Fox’s lead NFL game commentator to give the Raiders an unfair advantage. A quarter of the way into the list, can you blame them for believing Tom will look for any edge he can get?
Brady’s decision to un-retire and keep playing football was reportedly a key factor in his split with the Brazilian model after 13 years together, though Bundchen called those rumors “very hurtful.”
No further questions, your honor.2
Brady in his 2017 book, “The TB12 Method”:
When I was growing up, and playing outside in the sun, I got sunburned a lot. I was a fair-skinned Irish boy, after all. These days, even if I get an adequate amount of sun, I won't get a sunburn, which I credit to the amount of water I drink. I always hydrate afterward, too, to keep my skin from peeling. When I once told that to my sister, she said, 'You mean I don't have to use all those moisturizers and facial products to keep my skin looking good? I should just drink as much water as you do? I think you should market your TB12 Electrolytes as a beauty product.' I just laughed.
Not quite as crazy as saying water prevents concussions, but also probably not great medical advice.3
TB12 began selling 30-day supplies of Protect as the COVID pandemic raged. “I’m really proud to announce this amazing new product from TB12 that will provide you guys exactly what you need to stay healthy, strong and resilient for whatever comes your way,” Brady said in his pitch.
If only it could have protected him from…
Brady remains one of many high-profile targets in a lawsuit from FTX investors claiming the endorsers are liable for promoting the failed cryptocurrency exchange. He was as deep into the blockchain as any star, funding a separate NFT platform too. He just backed another crypto startup this spring 🤦♂️. The man loves a comeback story.
[redacted]4
This one Tom has owned up to. Last year he participated in a comedy roast on Netflix during which multiple comedians poked fun at his family.
Speaking afterwards on Logan Paul’s podcast (a crime in its own right), Brady said he was fine with all of the jabs thrown during “The Greatest Roast of All-Time” but… "I'll never forget when I talked to my kids the next day. It felt like a stake through the heart, and understandably. They're protective of their mom, of their dad, of everybody. 'What was the point of that? Why did you do that?'” He was reportedly paid $25 million to participate.
Five years before ~happening upon~ Matthew Stafford at a Montana ski resort, Tom Brady allegedly found himself on a yacht with Dolphins owner Stephen Ross. Brady reportedly discussed becoming a limited partner in the team as part of the franchise’s efforts to pair him with Saints coach Sean Payton. That run-in warranted penalties from the NFL, though Brady avoided any personal repercussions.
Deflategage, Brady’s signature scandal, resulted in him being suspended for four games in 2016, multiple court appearances, the Patriots being fined $1 million and giving up two draft picks, the NFL measuring football PSI in-game, Dave Portnoy handing out 70,000 towels featuring Roger Goodell with a clown nose—and ultimately the commissioner awarding Brady another Lombardi trophy at the end of the season.
If the current Raiders/Fox brouhaha plays out anything like that one, Brady will wind up just fine.
On the most recent Sporticast episode, Scott and Eben spoke about a recent women’s sports event we hosted in New York, and an NWSL owner that finally spoke the truth about a serious challenge facing the women’s soccer league 👇
Club Sportico is a community organized by Sportico, a digital media company launched in 2020 to cover the business side of sports. You can read breaking news, smart analysis, and in-depth features from Eben, Jacob and their colleagues at Sportico.com, and listen to the Sporticast podcast wherever you get your audio. Contact us at club@sportico.com.
Eben here. I did not know this last part before Jacob put together that blurb. Come on, Raiders!
Not sure what’s stranger, that Brady clip or the news segment overall…
These rankings were tallied after Jacob, Eben and Lev ranked each one on a scale of 1-5. Eben would like the readers to know that he would have given this a score of 12 if it was allowed. “One of the stupidest things a mega-star athlete has ever claimed, and that’s saying something.”
You never know who government censors might go after next