For 18 years, Donald Trump has been talking about how he could’ve had a Super Bowl–winning son-in-law instead of Jared Kushner. A look back at Trump’s long, lonely, and ultimately fruitless quest to make it happen
Tom Brady is the son-in-law that got away. Photo-Illustration: Intelligencer; Photos: Getty Images Imagine for a moment that you are Jared Kushner back in 2009. At just 28 years old, you’re already a real-estate magnate and publisher of the New York Observer. Best of all, you’ve reunited with your girlfriend Ivanka Trump, and things are getting serious; she’s converting to Judaism for you and you’re planning to pop the question.
Jared Kushner reportedly relays this anecdote in his book Breaking History: A White House Memoir, which is set to be released on August 23. It’s unclear if Kushner was distressed by Trump’s remark, but it’s something he, Ivanka, and Brady must be used to by now. Donald Trump has been openly dreaming about making Brady his son-in-law for nearly two decades, though the pair have expressed no interest in dating each other.
How did she feel about your remarks on Howard Stern’s radio show that New England Patriots quarterback Tom Brady is the only man good enough for her?I kid Tom, but he’s a friend of mine. I think he’s a great character. I got to know him when he was a judge at a jitterbug contest I entered after the Patriots won the Super Bowl. He’s a winner, and by that I mean every time he needs to make the pass he makes it.
“That was a long time ago in my life, so … No, there was never that where we ever dated or anything like that,” Brady replied, after some awkward laughing. In July 2018, the New York Times reported that people in the president’s orbit had heard him quipping that he could’ve had a more spectacular son-in-law:
He would joke that Ms. Trump could have married Tom Brady, the quarterback for the New England Patriots, and once joked to Robert K. Kraft, the team’s owner, that “Jared is half the size of Tom Brady’s forearm.”
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