Tom Brady's Biggest Mistake

Tom Brady Buccaneers, 2021. Photo courtesy of All-Pro Reels under CC BY-SA 2.0.

When you're Tom Brady — seven-time Super Bowl^® champion, global icon, and the golden boy of the NFL^® — it seems like you've done it all. But in May 2024, Brady signed up for a different kind of arena: the merciless battlefield of comedy. The result? Netflix's "The Greatest Roast of All Time: Tom Brady." And while the laughs were loud, the aftermath hit much closer to home — literally.

'It Was Tough on My Kids'

Brady's glamorous night at the Forum quickly turned into a parenting wake-up call. Speaking candidly on the "Impaulsive" podcast, Brady confessed, "It was tough on my kids for sure," according to PEOPLE.

He didn't sugarcoat the moment he realized he may have made a serious mistake. "There's some things as a parent you f--- up, and you don't realize until after," he admitted. "We're not perfect parents."

The next morning, after the jokes had stopped and the spotlight dimmed, Brady faced the toughest critics of all — his children. Jack, Benjamin, and Vivian wanted answers. Brady recalled that they asked, "What was the point? Why did you do that?" describing the exchange as a "stake through the heart."

What He Stood to Gain

So why did the G.O.A.T. step onto the comedy chopping block in the first place?

"I love when people were making fun of me. ... I just want to laugh, so I wanted to do the roast," Brady told The Pivot podcast, as reported by ESPN. In post-retirement haze, the football legend admitted he was craving some levity. "We loved laughing in the locker room. Let's do more of that and celebrate other people's success. That, to me, gives everyone a lot of hope," he added.

The roast promised nostalgia, camaraderie, and — let's be honest — a hefty paycheck. But what Brady didn't anticipate was how raw those jokes would feel the next day, especially for his children.

When the Jokes Cut Too Deep

Comedians like Kevin Hart and Nikki Glaser didn't hold back. Glaser, in particular, delivered the now-infamous zinger, reported by USA TODAY:

"Tom Brady. Five-time Super Bowl MVP, most career wins, most career touchdowns. You have seven rings — well, eight, now that Gisele (Bündchen) gave hers back."

The jokes about his highly publicized divorce from supermodel Gisele Bündchen were brutal — and Brady's kids felt every punchline.

To her credit, Glaser later expressed regret about the Gisele comment saying, " ... And if I ever met her, I would definitely apologize for hurting her feelings if she was indeed upset about it," she told PEOPLE.

But that didn't soften the blow for Brady's children, who remain fiercely protective of both their mom and dad.

The One Rule That Couldn't Be Broken

Interestingly, there was one boundary comedians refused to cross: the kids themselves.

"We all collectively just decided not to involve his kids too much in anything because they didn't ask for that," PEOPLE reported that Glaser revealed on "The Howard Stern Show." Yet even without being directly mentioned, the fallout from those family-focused jokes hit hard.

Will He Do It Again?

The verdict? Brady's answer is a resounding no.

Brady admitted on The Pivot, "It's the hardest part; the bittersweet aspect of when you do something that you think is one way and all of a sudden you realize 'I wouldn't do that again' because of the way it affected, actually, the people I care about the most in the world," ESPN reported.

Still, in classic Brady fashion, he's turning the regret into a growth moment. "I'm going to be a better parent as I go forward because of it," he said.

So, Was It Worth It?

From the standing ovations to the gut-wrenching conversations with his kids, this roast turned out to be a lesson in public image and personal consequence.

He may have survived countless sacks on the field, but this time, it was the emotional hits at home that left a lasting mark.

In the end, Brady proved that even living legends make mistakes. And when they do, they own them — publicly and unapologetically.

References: Tom Brady Calls His Netflix Comedy Roast a Parenting 'F--- Up' as His Kids Weren't Happy People Joked About Mom Gisele Bündchen | Tom Brady has regrets on roast, says he 'wouldn't do that again' | Tom Brady says he regrets Netflix roast, wouldn't do it again because it 'affected my kids'