Long before Tom Brady retired from the NFL or Ivanka Trump became a fixture in American politics, President Donald Trump had a vision, his daughter married to one of football’s most celebrated quarterbacks. While it never came close to reality, Trump’s repeated insistence on pairing Ivanka with Brady has been documented over the years.
Despite her long-standing marriage to Jared Kushner since 2009, Ivanka's father seemed unusually enthusiastic about the idea of a Brady-Trump union. So much so that he reportedly used the quarterback as leverage in conversations with Kushner during the early stages of his relationship with Ivanka.
In 'Breaking History,' Kushner’s 2022 memoir, recounted an interaction with Donald. “I could feel my voice shake as I managed to say that Ivanka and I were getting more serious and that she was in the process of converting.” Trump’s response was unexpected. “Well, let me ask you a question,” he said. “Why does she have to convert? Why can't you convert?”
After Kushner explained Ivanka’s decision was her own, Trump quickly pivoted. “That’s great. Most people think I’m Jewish anyway. Most of my friends are Jewish. I have all these awards from the synagogues. They love me in Israel.”
But it didn’t stop there. Trump then reportedly added a twist, saying his “good friend” Tom Brady had also been interested in his daughter. This wasn’t a one-off comment either, Trump has gone on record multiple times expressing admiration for Brady and his desire to see him as a potential son-in-law.
Back in 2004, speaking to Playboy, Trump was more candid. “I think Tom's a great guy, and I think he and Ivanka would make a great combination,” he said, as quoted by New York Magazine. He reiterated this sentiment on The Howard Stern Show, suggesting the two would have made a "power dynasty."
Brady has also spoken about the dating rumors. During a 2020 interview with Stern, Brady was clear. “That was a long time ago in my life. ... No, there was never that, where we ever dated or anything like that.” He also addressed Trump’s remarks. “He never suggested that to me. ... Look, it all worked out for me anyway. I married the woman of my dreams.” That woman, of course, was supermodel Gisele Bündchen, whom he married in 2009, eight months before Ivanka’s wedding to Kushner.
Today, Brady is focused on his kids and career following his divorce from Gisele, while Ivanka and Kushner, who share three children, Arabella, Joseph, and Theodore, have largely stepped back from public political life.
Ironically, Ivanka and Gisele have now become friends. Miami appears to have brought the two women closer, and earlier this month, the former political adviser and the Brazilian supermodel were photographed sunbathing together on Gisele’s luxury yacht.
Ivanka joined Gisele and her boyfriend, Joaquim Valente, in Miami, where the group enjoyed the weekend aboard the boat with friends and family, including Gisele’s daughter Vivian. Wearing matching black bikinis and colorful wraps, Ivanka and Gisele shared food, laughs, and proved their close friendship.