Trump Tried to Set Up Daughter Ivanka With NFL Legend Tom Brady — Prez Told Son-in-Law Jared Kushner He 'Wasn't Even Close' to His First Choice in Mortifying Moment
Ivanka Trump and Jared Kushner have been married since 2009.
Feb. 26 2026, Published 3:00 p.m. ET
Ivanka Trump has been married to her husband, Jared Kushner, for more than 16 years – but according to a bombshell new book, Donald Trump once tried to set her up with NFL legend Tom Brady instead, RadarOnline.com can reveal.
In Young Man in a Hurry: A Memoir of Discovery, California Governor Gavin Newsom details a particularly mortifying moment when the POTUS, 79, shamelessly told the whole story in front of Kushner.
'What Do You Mean You're in Love?'
Tom Brady asked Donald Trump for Ivanka's phone number, according to a new book.
According to Newsom, Donald said that Brady – who was single at the time, as this was prior to his marriage to Gisele Bündchen – "expressed an interest" in dating Ivanka and asked him for her phone number after they met at a social function.
"Trump gave it to him. Brady called Ivanka and left a message, but she never called him back," Newsom writes in the tell-all. "Soon after, Brady related the snub to Trump, who then called his daughter, wondering what was up."
'"I said, Jesus, you know, Tom Brady. What the h--- is going on? Why aren't you calling this guy back?" the governor recalls Donald saying to him. "And she tells me, 'Oh, I'm in love.' What do you mean you're in love? And that's when she mentions this guy. This guy right here. "
'It Was Dead Air for a Moment'
Donald Trump reportedly said Jared Kushner wasn't 'even close' to his first choice for Ivanka.
Gesturing to his son-in-law, the president added, "I said to Ivanka, 'Not the guy whose father just got out of prison?'" referring to Charles Kushner, who served just over a year behind bars after pleading guilty to more than 15 criminal counts in the early 2000s.
"It was dead air for a moment," Newsom pens of the awkward back-and-forth between Donald and his son-in-law. "Kushner wore a face that somehow retained its impassivity. He finally muttered, with the slyest grin, 'Yes, sir. I know I wasn't your first choice.'"
'Not Even Close'
Gavin Newsom's book was released on February 24.
Instead of apologizing, Newsom says Donald turned to him and quipped, "'Not even close, right, Gavin? Tom Brady. Tom Brady.'"
"In front of the governor and future governor of California, Trump was making his son-in-law feel two feet tall," Newsom recalls. "And Kushner just let him do it."
Following his failed attempts at dating Ivanka, Brady went on to tie the knot with Brazilian model Bündchen in 2009 and they welcomed two children together. Years later, the pair announced their divorce in 2022.
Donald Trump's History of Jabs at Jared Kushner
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Despite the fact that Donald appointed Kushner to serve as a senior advisor at the White House during his first term in office, this isn't the first time the POTUS has been caught bad-mouthing his son-in-law.
As Radar previously reported, an insider claimed that "nobody ever talks" about how much "Trump complains about Jared."
Back in 2017, Donald also reportedly joked he was a "little bit upset" because Kushner had become "much more famous" than him.
