Were Tom Brady And Ivanka Trump Ever A Couple? Donald Definitely Wishes They Were
Ivanka Trump, daughter of controversial U.S. President Donald Trump, has been married to real estate developer Jared Kushner since 2009. However, there was a time when Ivanka's father seemed weirdly obsessed with the idea of her marrying now-retired NFL quarterback and seven-time Super Bowl champion Tom Brady, even if the prospect of such a romance never seemed to exist anywhere outside the president's mind.
In his 2022 book "Breaking History," Kushner claimed that Donald tried to scare him once he made it clear he planned on marrying Ivanka. According to Kushner, Donald did this by suggesting that Brady was also interested in his daughter. This wasn't an isolated incident, either. In an April 2020 episode of "The Howard Stern Show," the eponymous host recalled Donald telling him that he wanted Ivanka and Brady to get together and form a "power dynasty."
But you don't have to take their word for it. Donald Trump himself made his thoughts clear while chatting with Playboy in 2004, back when Brady was only about four years into his 22-year pro career (but already had two Super Bowl rings). "I think Tom's a great guy, and I think he and Ivanka would make a great combination," Donald said in the interview, per New York Magazine. He and Brady became friends after first crossing paths in 2001. In more recent times, though, Brady has downplayed the nature of his relationship with Donald. "I haven't talked to him in a lot of years," he told Variety in 2022.
Tom Brady says he and Ivanka Trump were never an item
In addition to seemingly trying to distance himself from Donald Trump, Tom Brady has also asserted that there was never any kind of romance between himself and Ivanka Trump. It was in 2020 that Howard Stern asked Brady point blank if there was ever anything between the two. "That was a long time ago in my life. ... No, there was never that, where we ever dated or anything like that," Brady told Howard Stern in 2020.
Furthermore, while Donald stated on more than one occasion that he would have liked to see Ivanka and Brady get together — including during his own chat with Stern — the businessman turned politician apparently never told Brady that directly. "He never suggested that to me. ... Look, it all worked out for me anyway. I married the woman of my dreams," Brady added, further explaining, "I think I married the most amazing woman, so I have no regrets."
Brady was referring to model Gisele Bündchen, whom he wed in February 2009 — eight whole months before Ivanka and Jared Kushner tied the knot in October. However, Brady and Bündchen ended up calling it quits in 2022. Despite her divorce from the New England Patriot turned Tampa Bay Buccaneer, Bündchen continues to live quite the lavish life. Meanwhile, Brady himself has settled into a role as an NFL commentator following his retirement from the on-field action.
Could Ivanka Trump and Tom Brady have worked as a couple? An expert weighs in
What if fate had dealt another hand and Ivanka Trump had indeed decided to give things a shot with Tom Brady like her father wanted? Would Gisele Bündchen have ended up with Jared Kushner? Probably not. But we asked an expert if Ivanka and Brady would have actually been compatible — and more importantly, if they would have lasted.
According to Susan Trombetti, matchmaker and CEO of Exclusive Matchmaking, not only does Ivanka's father Donald Trump obviously approve of Brady, but she and the NFL star also have comparable lifestyles. "Both are used to being in the spotlight and media with their high-profile statuses," Trombetti exclusively told The List. "It's better when that happens because they know the media game and how to avoid negative behaviors that create scandalous headlines," she added.
That said, Ivanka Trump and Tom Brady are still who they are at the end of the day, which may have made it hard for them to go the distance romantically — even in this hypothetical version of events. "When it comes to staying power, I think Tom would have run into the same issues as he did with Gisele: not being present enough and letting his ambition take over his life," Trombetti explained. "I think given that during the last 4-year presidency of Trump, Ivanka lived and breathed for her dad's presidency ... They would have been separated too much."