Donald Trump is all about his image, status, and family brand, and he will block anyone who tries to get in the way.
Therefore, it’s no surprise that he meddled in his kids’ love lives, wanting each to choose the best suitor for a husband or wife. The protective-dad routine can be sweet, but also sharp.
A new report suggests that Trump has someone in mind to date and marry his daughter, Ivanka, rather than her husband, Jared Kushner.
According to rival Gavin Newsom, Trump wanted Ivanka to pair 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 mentioned that Ivanka was already in a relationship with Jared Kushner and made a sharp remark about Kushner’s father having served time in prison. This incident reportedly occurred with Kushner sitting nearby, along with Newsom and former California Governor Jerry Brown.
Trump allegedly tried to set his daughter up with NFL legend Tom Brady, only to realize that she was “already dating some guy whose father had recently been released from prison.”
“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.
Fifteen 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 person who didn’t believe Newsom’s story wrote, “Whoa, you’re implying Newsom’s word is gospel? I think not.”
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.
Great Job Nicole Duncan-Smith & the Team @ Atlanta Black Star for sharing this story.
