Donald Trump Warned Jared Kushner That Tom Brady Was Also Trying to Court Ivanka Trump

Donald Trump has always had a Tom Brady obsession, and now, we might know the reason why. Jared Kushner is offering insight into his courtship of Ivanka Trump in his upcoming book, Breaking History: A White House Memoir, and it surprisingly involves the NFL star.

Kushner and Donald Trump got off to a rough start because he was the publisher of the New York Observer at the time. His future father-in-law sent off an angry missive to him when he didn’t like his standing on the magazine’s annual “Power List” in 2007. “Please stop sending me your paper, so I don’t have to read bullshit like this anymore!” Trump wrote in an excerpt provided to Forward. That ego-driven letter sounds about right and it was a warning sign to Kushner, which he obviously didn’t heed.

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Two years later, Kushner was dating Ivanka, and was time to start discussing possible proposal details to Donald Trump and her conversion to Judaism. “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,” Kushner wrote. “Well, let me ask you a question,” Donald Trump asked his future son-in-law. “Why does she have to convert? Why can’t you convert?” Noting that it was Ivanka’s decision to make, Donald Trump also added a bit of competition into the mix for Kushner, reminding him that Brady still had an interest in his daughter, so he better have the best intentions with the upcoming proposal.

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That isn’t exactly how the story went down, according to the Tampa Bay Buccaneers quarterback. Howard Stern mentioned to Brady in a 2020 interview that he knew that “Trump always dreamed of you marrying Ivanka,” and he pressed on to ask the athlete if they ever dated. “That was a long time ago in my life,” Brady answered awkwardly. “No, there was never that where we ever dated or anything like that.” And if you know the Brady-Gisele Bündchen timeline, then you know they married in 2009, the same year Kushner walked down the aisle with Ivanka. So it seems that Donald Trump was playing wishful matchmaker in his head because he wanted Brady as his son-in-law — and nobody else was onboard with this scenario.

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