Donald Trump once fumed over his daughter Ivanka missing out on the chance to date Tom Brady – while son-in-law Jared Kushner was sat right next to him.
In an excerpt from his new book ‘Young Man in a Hurry: A Memoir of Discovery’, California Governor Gavin Newsom recalled his awkward first meeting with Trump in 2018 while on board presidential helicopter Marine One during his first term in office.
As well as discussing the recent wildfires in California at the time, Newsom says he and the president also enjoyed a bizarre conversation about his eldest daughter, and specifically her missed opportunity with Brady.
Trump, who is said to have claimed that Brady asked him for Ivanka’s phone number, was speaking about the star NFL quarterback’s football ability when ‘his riff took a strange turn’, Newsom remembers.
‘He recounted that when Brady was single, the two of them were at a function and Brady expressed an interest in dating his daughter Ivanka,’ he continued. ‘The quarterback asked for her number, and Trump gave it to him. Brady called Ivanka and left a message, but she never called him back.
‘Soon after, Brady related the snub to Trump, who then called his daughter, wondering what was up.
Donald Trump once fumed over daughter Ivanka (center) missing out on dating Tom Brady while son-in-law Jared Kushner (right) was next to him
Trump told California Governor Gavin Newsom that Ivanka could have dated the NFL legend
‘”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.” Trump said, pointing to his son-in-law.
‘”This guy right here. This Kushner guy: I said to Ivanka, Not the guy whose father just got out of prison?”
‘It was dead air for a moment. 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.”
‘And then Trump turned to me and said, “Not even close, right, Gavin? Tom Brady. Tom Brady.’
Newsom recalled that he either ‘winced or stifled a laugh’ during the excruciating exchange.
‘In front of the governor and future governor of California, Trump was making his son-in-law feel two feet tall,’ he added. ‘And Kushner just let him do it.’
Kushner – whose father Charles, a wealthy real estate magnate, once spent 14 months in prison for tax evasion, witness tampering and illegal campaign contributions – first met Ivanka in 2005 through mutual friends before tying the knot in 2009.
The couple have three children together in daughter Arabella Rose, 14, and sons Joseph Frederick, 12, and Theodore James, nine.
Kushner first met Ivanka in 2005 through mutual friends before tying the knot in 2009
The president’s eldest daughter has now been married to Kushner for close to 17 years
He has taken on an advisory role in each of his father-in-law’s two spells as president
During a 2020 interview with Howard Stern, Brady was grilled about Trump’s desire for him to date his daughter, but insisted he never came close to doing so.
‘Trump always dreamed of you marrying Ivanka, and he told me he suggested it to you – but did you ever go out with her?’ Stern asked.
‘That was a long time ago in my life… No, there was never that, where we ever dated or anything like that,’ Brady said, before referencing his own daughter, Vivian.
‘I have a daughter… would I ever arrange my daughter…’ he added as Stern cut him off.
‘I know, it’s weird,’ the radio host said.
In 2019, a former Trump adviser revealed how he once gave Brady a call to wish him a happy birthday, and couldn’t resist teasing him that Ivanka was ‘the only thing that you weren’t able to win.’
‘Ivanka chose Jared,’ he told the New England Patriots quarterback, former top campaign adviser Jason Miller said on the Daily Beast’s Omnihambles podcast.
Amid his marriage to Ivanka, Kushner worked as a senior advisor to Trump in his first stint as president from 2017-21. Since his father-in-law returned to office, he has taken on an informal advisory role and served as an intermediary in negotiations regarding the Israel-Gaza and Ukraine-Russia wars.
Kushner has played an important role in negotiations to end both the Gaza and Ukraine wars
Along with special envoy to the Middle East and peace missions Steve Witkoff, he played a key role in delivering Trump’s Gaza peace deal in October 2025, which entered its first phase when Israel and Hamas agreed to a ceasefire that month.
The pair are also now locked in negotiations to end Iran’s nuclear ambitions and halt Russia’s rapacious landgrabs in Ukraine.
However, having landed an important role in office through his marriage to Trump’s daughter, Kushner has earned a nickname from his Russian and Iranian counterparts across the negotiation table.
In Moscow it’s ‘Zyat’ and in Tehran it’s ‘Damad’, both of which translate to ‘son-in-law’.
Brady, meanwhile, dated actress Bridget Moynahan from 2004-06 and welcomed a child with her, now 18-year-old son Jack, before going their separate ways.
The seven-time Super Bowl winner, who was playing for the New England Patriots when Trump claimed Ivanka once had the chance to date him, entered a relationship with Brazilian supermodel Gisele Bundchen shortly after.
Brady is yet to enter a serious relationship since his 2022 divorce from Gisele Bundchen
The legendary NFL quarterback has been linked romantically to influencer Alix Earle of late
He married Bundchen in February 2009 and welcomed another two children with her – son Benjamin, now 16, and daughter Vivian, now 13 – before divorcing in October 2022.
Since splitting from Bundchen, Brady has been linked with a number of high-profile women including Kim Kardashian, Irina Shayk and Alix Earle.
In recent months he has been spotted cozying up to stunning influencer Earle on two separate occasions, with the pair first seen getting close at a New Year’s Eve party in St. Barths.
Footage also emerged this month of Earle, who recently split from NFL star Braxton Berrios, dancing with Brady at a pre-Super Bowl party in San Francisco.
