A chat turned painfully awkward for Kushner.

Donald Trump once joked that his daughter, Ivanka Trump, could have dated NFL star Tom Brady. He made the comment while sitting next to his son-in-law, Jared Kushner. California Governor Gavin Newsom shared the story in his new book, Young Man in a Hurry: A Memoir of Discovery.

Newsom said the moment happened during a 2018 flight on Marine One. He had met with Trump to talk about wildfires in California, but the conversation changed topics. Trump started talking about Tom Brady and then about Ivanka.

According to Newsom, Trump said that when Brady was single, he once asked for Ivanka’s phone number. Trump said he gave Brady the number and that Brady called her, but Ivanka never called him back.

An Awkward Moment On Marine One

Ivanka Trump (Photo via Instagram)
Newsom wrote that Trump could not believe his daughter ignored the quarterback. He quoted Trump saying, “I said, Jesus, you know, Tom Brady. What the hell is going on? Why aren’t you calling this guy back? 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.” Ivanka replied that she fell in love. She meant Jared Kushner.

Trump then pointed at Kushner. Newsom quoted him saying, “This guy right here. This Kushner guy.” He added, “Not the guy whose father just got out of prison?” Newsom described a brief silence. He said Kushner kept a straight face. Kushner then replied, “Yes, sir. I know I wasn’t your first choice.”

Newsom said Trump turned to him and repeated Brady’s name for emphasis. “Not even close, right, Gavin? Tom Brady. Tom Brady.” Newsom admitted he either winced or tried not to laugh. He wrote that Trump made his son-in-law feel small in that moment.

Jared Kushner’s father, Charles Kushner, spent 14 months in prison for tax evasion, witness tampering, and illegal campaign contributions. Jared married Ivanka in 2009, and they have three children.

Brady later addressed the rumor during a 2020 interview with Howard Stern. Stern asked him if he ever dated Ivanka. Brady replied, “No, there was never that, where we ever dated or anything like that.” He added that he would not arrange his own daughter’s dating life.

The story shows Trump’s direct and sometimes a pure raw personality. At one point, he even reportedly teased Tom Brady about his then-wife Gisele Bundchen’s looks while they were still married.