‘Brady Was Smart Not to Get Mixed Up: Trump’s Icy Take on Ivanka’s Husband Says It All as Fans Point to His Rift with the NFL Star She Never Chose
Donald Trump is a man who rarely filters his thoughts, especially when it comes to his image, status, and the family brand.
Therefore, it’s no surprise that he meddled in his kids’ love life, wanting each to choose the best suitor for a husband or wife. The protective-dad routine can be sweet, but also sharp.
In Trump’s case, that sharpness allegedly extended to the idea that his son-in-law, Jared Kushner, wasn’t good enough or didn’t have enough funding or access for his daughter, Ivanka.
According to rival Gavin Newsom, Trump allegedly told a story about once wanting to set Ivanka up with an NFL legend.
Details about the exchange were found in Newsom’s book, “Young Man In A Hurry,” in which the California governor recounts a 2018 trip on Marine One following devastating wildfires.
Instead, he remarked, Ivanka was already dating Kushner — adding a cutting aside about Kushner’s father spending time in prison. The moment reportedly unfolded with Kushner seated nearby, along with Newsom and then-California Gov. Jerry Brown.
“In front of the governor and future governor of California, Trump was making his son-in-law feel two feet tall,” Newsom writes, according to The Atlantic, which reported the book. “And Kushner just let him do it.”
Charles Kushner began a two-year sentence after pleading guilty to charges of tax evasion, witness tampering, and illegal campaign contributions in 2005. Four years later, his son married Ivanka in 2009. Jared is now a diplomatic envoy in the Trump administration, and his presence during briefings about foreign policy or the Middle East often raises red flags.
15 years after his conviction and release, Charles was granted a pardon by Trump during his first term as president in 2020, and later became the U.S. ambassador to France after Trump won in 2024.
The anecdote struck many as more than just fatherly ribbing, and Yahoo! News readers lit up once the story began circulating again.
“I agree with tRUMP’s assessment of Kushner….that being said….he’s perfect for tRUMP’s vacuous daughter!” one wrote.
Another chimed in with a hypothetical scenario: “I can see trump talking to men wanting to date Ivanka. Yes, you want to go out with my daughter. Have you ever gone to jail. NO, get out.”
A third widened the lens and noted the obvious similarity: “Both Jared and Ivanka’s fathers are convicted felons,” while someone else offered, “Trump was upset that Tom Brady wasn’t dating his ‘hot’ daughter.”
For many, Brady is the true winner for dodging a bullet that would have tied him to Trump as family.
“Brady was smart to not get mixed up in that family. Trump just sees people as someone to use to further his own self-aggrandizement. Aggrandizement is the act of increasing the power, wealth, status, or prestige of oneself or an entity. It often carries a negative connotation of vanity or exaggerated self-importance, known as self-aggrandizement.”
One commenter added a more pointed accusation: “Jared Kushner is working behind the scenes to dramatically inflate the Trump Dynasty’s wealth.”
Trump’s fixation on star power and winning has long shaped his worldview, and Brady — decorated, famous, and synonymous with championships — fits neatly into that mold. Kushner, by contrast, has often presented a quieter, more reserved public persona.
Trump and Brady’s once-friendly dynamic has morphed into something far more layered. Trump once hailed Brady as the ultimate “winner,” even rushing to his defense during the 2016 Deflategate controversy.
But the tone shifted when Brady began keeping his distance — most notably by skipping the Patriots’ 2017 White House visit — a move that reportedly didn’t sit well and quietly cooled their public rapport. Trump was likely even more angered that Brady went to the White House during Joe Biden’s presidency after the Buccaneers’ Super Bowl win in 2021.
That revived story arrives alongside fresh scrutiny of Ivanka’s current public appearances.
Over the past year, Ivanka’s solo appearances have fueled quiet chatter about her marriage. From summer yacht outings in Miami with high-profile friends, including Brady’s ex-wife, Gisele Bündchen — and no Jared in sight — to social media posts where she appeared without him and at times without her ring, each sighting has reignited speculation about what’s really going on behind the scenes.
Ivanka and Kushner’s relationship dates back to at least 2007, culminating in their 2009 wedding. They later served as senior advisers during Trump’s first term, navigating political storms side by side.
Brady and Gisele also wed that same year in 2009. Their relationship spanned nearly 16 years, starting in 2006 and culminating in a 13-year marriage. The pair built a family together with two children before ending their union in October 2022.
But in a family where personal dynamics are rarely private, even an old comparison can echo years later — especially when the audience is always watching for clues.