Don Jr.'s Alleged Ex Throws Shade At Jesse Watters' Wedding Prediction

The Fox News host creepily suggested Barron Trump and Sydney Sweeney could “create the greatest political dynasty in American history.”
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Fox News host Jesse Watters is being brutally mocked for a mega-cringy wedding prediction he made on Monday’s episode of “The Five,” but the biggest shade was thrown by an alleged ex-girlfriend of Donald Trump Jr.

It happened during a segment where Watters discussed the reaction to Sydney Sweeney’s recent American Eagle ad ― which some have suggested promotes white supremacy ― and the revelation that the actor is a registered Republican.

In a MAGA fever dream, Watters predicted that the 27-year-old “White Lotus” actor would marry 19-year-old Barron Trump and “create the greatest political dynasty in American history.”

Watters: You know how this ends? Sydney Sweeney is going to marry Barron Trump and it's going to create the greatest political dynasty in American history. pic.twitter.com/O41vvSlxwd

— Acyn (@Acyn) August 4, 2025

Watters’ suggestion was so over the top that it attracted a special type of internet snark.

However, the biggest shade thrown at him came from former Danity Kane member Aubrey O’Day, who allegedly had an affair with Don Jr. between 2011 and 2012, around the time she was on “The Apprentice” and he was still married to Vanessa Trump.

Although Don Jr. never admitted to the affair, Donald Trump’s former attorney Michael Cohen allegedly killed a story in 2013 that Us Weekly was preparing about it.

O’Day responded to Watters’ Sydney Sweeney-Barron Trump wedding prediction Monday night:

until he falls in love with his mistress. They always want more than who they married. https://t.co/AVHQeCDIZd

— Aubrey O'Day (@AubreyODay) August 5, 2025

Despite the blunt comments about the Trump family men, O’Day may still be carrying an itty-bitty torch for Don Jr.

Earlier this summer, she told US Weekly that the president’s oldest child made her feel the “most beautiful,” and “made me feel the smartest and the most beautiful, but he loved my mind more than anything else, and that’s what I love about me. The way that we loved was we loved the same.”

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