"Ivanka chose Jared" - Donald Trump once mocked NFL GOAT Tom Brady for 'one thing he couldn't win'

Ivanka Trump is married to Jared Kushner, though Donald Trump once wanted her to marry Tom Brady
Ivanka Trump is married to Jared Kushner, though Donald Trump once wanted her to marry Tom Brady
Ian Van Roy

It is well known that former US President Donald Trump and quarterback Tom Brady have built up a friendship over the last 20 years. While Brady was winning Super Bowls, Trump was winning television ratings and elections.

However, in a 2004 interview with Playboy (via Intelligencer), the former President revealed one thing that the quarterback couldn't win.

In the interview, Trump said TB12 couldn't win his daughter as someone else had already done so. Here's how he put it:

"I kid Tom, but he’s a friend of mine. I think he’s a great character... He’s a winner, and by that I mean every time he needs to make the pass he makes it..."

He continued to praise Brady, but said he would have to look elsewhere:

"I think Tom’s a great guy, and I think he and Ivanka would make a great combination... My daughter has a boyfriend and she’s happy with him, but Tom Brady would make any father-in-law proud."

According to the Omnishambles podcast (via Intelligencer), Trump left a voicemail for the quarterback on his birthday in 2016 with a mostly orthodox message, but took a dig at his inability to win over his daughter.

The message was heard by Jason Miller, Trump's former campaign adviser. Here's how he summed up what he heard:

"Ivanka chose Jared. That’s the only thing that you weren’t able to win at.”

The quarterback, of course, eventually went on to marry Gisele Bundchen in 2009. The two have been happily married since.

.@maxkellerman ratio + I have a swimwear line now 👍…

Tom Brady's biggest wins

Tom Brady at Super Bowl LV
Tom Brady at Super Bowl LV

Of course, Tom Brady won at pretty much every other big opportunity. Most agree that the Super Bowl is, by definition, the most important game to win. As such, each of the quarterback's Super Bowl victories are one of the biggest wins of his career.


According to WSN, his first Super Bowl win came in 2001, when the New England Patriots defeated the St. Louis Rams. His next big win came in 2003, when he earned a Lombardi after defeating the Carolina Panthers. In 2004, the quarterback won another Super Bowl by defeating the Philadelphia Eagles.

It took 10 years, but he finally won his next Super Bowl in 2014 after defeating the Seattle Seahawks in one of the most famous goal-line stands in NFL history. In 2016, the quarterback led arguably the most famous comeback in league history against the Atlanta Falcons after falling behind 28-3.


In 2018, the quarterback beat the Los Angeles Rams to earn yet another ring. Most recently, in 2021, he defeated the red-hot Patrick Mahomes in the biggest Super Bowl blowout of his career.

It was only the second time in NFL history that a starting quarterback won a Super Bowl with two different franchises. In total, he has seven championships.

Edited by Akshay Saraswat


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