When did Adin Ross stream with Donald Trump? Streamer says he will be asking the US president about the Epstein files if he interviews him again

After gifting Trump luxury items live on stream, Adin Ross now says he’ll focus on the Epstein files if there’s another interview.

In early August 2024, internet personality Adin Ross pulled off one of the most unexpected livestream events of the year: a sit-down with former U.S. President Donald Trump on the streaming platform Kick. The streamer, whose rise has been marked by both viral success and controversy, managed to secure Trump as a guest for a broadcast that attracted hundreds of thousands of live viewers. 

Gifts of a golden Rolex and a customized Tesla Cybertruck punctuated the encounter, raising questions about campaign finance and influence in real time. Now, months later, Ross has announced that if he is fortunate enough to conduct a second interview with Trump, he plans to press him on the Epstein files, a volatile topic that has resurfaced in public debate. This announcement adds a charged new dimension to what was already one of the most talked-about streaming events of the political cycle.

When did Adin Ross stream with Donald Trump, and what’s next?

On August 5, 2024, Adin Ross hosted Donald Trump in a livestream at Trump’s Mar-a-Lago residence on the Kick platform. That stream turned into a spectacle from the start. Viewership soared, marking Ross’s most-watched broadcast ever and placing it among the top live events across platforms. Ross kicked off by joking that viewers might expect yet another impersonator, only to reveal that the guest was the real deal, former President Trump.

Throughout the roughly 80-minute stream, Ross not only interviewed Trump but also presented him with extravagant gifts, first a Rolex watch, then a Tesla Cybertruck customized with patriotic imagery. Trump called both gifts “incredible,” though campaign officials later acknowledged they would consult the Federal Election Commission, as the combined value far exceeded the legal contribution limits of $3,300 per election cycle.

Besides the flashy gifts, the stream had a lot of moments that felt a little unexpected. Adin Ross showed up in campaign gear and brought up all kinds of topics, from serious stuff like criminal justice to lighter things in pop culture. He even tossed in some slang and jokes that seemed aimed at keeping younger viewers interested. At one point, Trump mentioned that his son Barron actually pushed him to do the stream, which made sense considering Ross’s big following with teens.

Now people are wondering if there’s going to be another stream, and Ross has already said he’d change things up if it happens. This time, he wants to bring up the Epstein files, which are a collection of documents tied to Jeffrey Epstein, who was a convicted sex offender. These files have fueled tons of conspiracy theories online. Back in 2025, though, the Department of Justice and FBI said there wasn’t any proof of a secret client list or blackmail, and they decided not to keep investigating. Even so, just bringing it up makes the topic really sensitive and politically charged.

Ross’s decision to raise the Epstein files shows us how deeply streaming platforms now intersect directly with political discourse. By pivoting toward a matter as controversial as the Epstein files, Ross is signaling a readiness to push beyond spectacle and testing whether mainstream political figures will engage in such scrutiny on unconventional stages.