Why Kimberly Guilfoyle & Donald Trump Jr.'s Relationship With Russell Brand Is So Strange

If there is one thing true about the Trump family, it's that they never fail to surprise. For example, Donald Trump Jr. and Kimberly Guilfoyle suddenly cozying up with the legally besieged Brit comedian Russell Brand. Being close to a controversial and alleged law-breaker is no biggie for Don Jr. and Guilfoyle, given Donald Trump's myriad of trials. Still, there's something decidedly strange about the two being besties with Brand.

Following Brand and Katy Perry's divorce in 2012, Brand's become increasingly tendentious, seemingly by the day. Brand has reinvented himself into some kind of alt-right figurehead, sharing his pearls of wisdom, spreading conspiracy theories, and regularly expressing his hatred for the "mainstream media" to his 6.8 million subscribers on his YouTube channel. But, for obvious reasons, none of that makes his relationship with Don Jr. and Guilfoyle strange. It's Brand's past history with the Donald Trump, followed by his sudden conversion, that's so odd.

Donald and Brand were in a social media war a decade ago. "I watched Russell Brand @rustyrockets on the @jimmyfallon show the other night—what the hell do people see in Russell—a major loser!" Donald posted on X, formerly Twitter, in October 2014. "@realDonaldTrump are you drunk when you write these tweets? Or does that foam you spray on your bald head make you high?" Brand clapped back. However, as Brand has become increasingly divisive, the tide has changed, resulting in his strange relationship with Guilfoyle and Don Jr.

Kimberly Guilfoyle and Donald Trump Jr.'s strange relationship with Russell Brand has blossomed as the comedian's conspiratorial beliefs have ramped up. They appear to have begun buddying up in February 2023 when Guilfoyle posted an Instagram photo of the three looking decidedly cozy. But Don Jr. and Brand have formed a particularly strong bromance.

In a June 7 Instagram reel, Don Jr. announced Brand would be a guest on his "Triggered" podcast. He shared they'd discuss Brand's "path away from Hollywood and some of that insanity. The attacks that he's faced." Don Jr. later admitted, "Ten years ago, I imagine we wouldn't have agreed on much politically." But my, how things change. "I had a wonderful time with @DonaldJTrumpJr while here in Florida. We have stellar conversations like this and more over on @rumblevideo and @OnLocals," Brand posted on Instagram later the same evening, along with a photo of the two enjoying cigars.

Both Brand and Don Jr. are increasingly turning to Rumble, a streaming platform popular among the alt-right that claims to be "immune to cancel culture." Brand launched his daily live show, "Stay Free with Russell Brand," in September 2022. He shares a seemingly endless stream of pro-Trump videos with his 1.89 million followers. Meanwhile, Don Jr. streams his podcast to his 1.4 million subscribers.