Tom Brady Dragged at Roast Over Breakup With Then-Pregnant Bridget Moynahan

During the first hour of The Roast of Tom Brady, there was endless jokes about his ex-wife, Gisele Bündchen, but Nikki Glaser was the first comedian to make a reference to the quarterback’s ex Bridget Moynahan.

“Tom, you’re the best to ever play for too long, you retired then came back then retired, I get it … Kt’s hard to walk away from something that isn’t your pregnant girlfriend,” Glaser said on the live Netflix special on Sunday, May 5. “To be fair he didn’t know, he just thought she was getting fat.”

Brady and Moynahan had been dating for more than two years when they called it quits in 2006. Two months after he moved on with Bündchen, Moynahan learned she was pregnant. Moynahan gave birth to their son John, whom they call Jack, in August 2007.

Not long after an unexpected cameo from Kim Kardashian at Friday’s roast, Will Ferrell (in character as Ron Burgundy) made the second joke of the night about Moynahan.

Look Back at Tom Brady and Bridget Moynahan’s Rocky Relationship

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A complicated past! Tom Brady and Bridget Moynahan welcomed their son, John, after their relationship was over and the New England Patriots star had already moved on with Gisele Bündchen. “Two months into our relationship, Tom told me that his ex-girlfriend was pregnant. The very next day the news was everywhere, and I felt my […]

“The last time this guy went truly deep, he ended up paying child support to Bridget Moynahan,” the actor quipped.

While Moynahan does not appear to be present at Friday’s roast, she’s on good terms with Brady and continued to coparent Jack, now 16, with him. It wasn’t always easy, however, with the Blue Bloods actress making her first statement about the situation in the July 2008 issue of Harper’s Bazaar.

“I’m not sure anyone — and I could be wrong in this — grows up thinking, ‘I want to be a single mom,’” Moynahan explained at the time. “When you’re suddenly pregnant and no one is standing by your side, even if you’re in your 30s, it’s a hard conversation. I’m a traditional girl, and I believe in marriage, and I just always thought that’s the way I’d be doing this. For a moment, it was hard for me to accept that this was the way I was going to have a family.”

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Related: Tom Brady’s Complete Dating History: From Bridget to Gisele and More

Throughout his career in the NFL — which saw him win seven Super Bowls — Tom Brady also made headlines for his numerous A-list romances. Brady dated Bridget Moynahan from 2004 to 2006, welcoming their son, Jack, in 2007. The now-retired Tampa Bay Buccaneers quarterback was already dating future wife Gisele Bündchen when Moynahan found […]

Moynahan recalled “sobbing” when she went home with Jack alone, but she didn’t say a bad word about the athlete.

“There’s no reason why my son, years down the line, would need to read anything [personal] about his mother or his father,” she said.

Brady would go on to marry Bündchen and welcome son Benjamin and daughter Vivian. They split in 2022 after 13 years of marriage.

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