Trump Gives Don Jr. and Eric the Ivanka Treatment With Creepy ‘Threesome’ Joke

There is but an exploding anthology of all the nasty, ugly, and disturbing things Trump says—but, even today, few things top the creepy remarks he’s repeatedly made about his daughter, Ivanka. 

We’ve got a full list here—but before we go any further, here’s a short recap. In 1997, while 16-year-old Ivanka was hosting the Miss Teen USA pageant, Trump asked the then-Miss Universe if she thought his daughter was “hot.” “She’s hot, right?” In 2006, on ABC’s “The View,” he told hosts that “I’ve said if Ivanka weren’t my daughter, perhaps I’d be dating her.” And according to a 2023 book by Miles Taylor, a former White House advisor that worked in Trump’s first term, the president apparently made several comments about his daughter’s boobs and butt—and openly wondered what having sex with her would look like. 

Unfortunately, none of this is new. But on Wednesday, Trump revived his creepy ol’ family joke—and this time, extended the treatment to his two sons, Eric and Don Jr. Yikes!

Trump: I see my two beautiful sons sitting there. I think I’m going to give one medal of honor to myself, one to them, and we’ll have a threesome.

[image or embed]

— Headquarters (@headquartersnews.bsky.social) July 1, 2026 at 9:20 PM

 

In a speech at the opening of the Theodore Roosevelt Presidential Library in North Dakota, Trump talked about Roosevelt’s Congressional Medal of Honor when he floated adding his own to his wall of undeserved and usually fake accolades, and… made things weird. “Now, as I see my two beautiful sons sitting there, I think I’m going to give one to myself, one to them, and we’ll have a threesome, OK?” he said, referring to the medal.

“I’ll pick out one of the two, I’ll give them the Congressional Medal of Honor for something, for their genius at hunting, and I’ll get one for taking on Russia, Russia, Russia, [sic] or something.” Jesus. Forget the Freudian slip; this feels more like a Freudian landslide.

And as much as Trump might drool over a Congressional Medal of Honor, it’s the country’s highest military accolade and reserved solely for military servicemembers who are distinguished “conspicuously by gallantry and intrepidity at the risk of his life above and beyond the call of duty.” Roosevelt is the only president to have received such an award, and it was only given to him in 2001 by Bill Clinton for his role in the Spanish-American War. And, um, I’m no expert in the armed forces, but I assume someone who’s avoided being drafted five times isn’t really the picture-perfect example of gallantry. 

But leave it to Trump to convince himself that he’s not only level with the legacies of presidents past—but friends with them, too. During the library event, he appeared to receive a pep talk from an AI-ified Roosevelt, in which the more-than-centuries-old leader told him that “every day a president faces storms most people never see, but if you keep your nerve and remember the nation comes first, you get through.” “I know you know that feeling yourself,” the AI Roosevelt told Trump. “Those words are fantastic, the president replied. “I just want to say it’s an honor to be with you today.” Damn. Can’t wait to see what AI Hoover has to say next.