Donald Trump & Rosie O'Donnell Have Been Fighting Longer Than You Realized

It's no secret that Donald Trump has a laundry list of enemies, including once-close allies who have since turned their backs on the president. While they were certainly never pals, one public figure who has been vocally critical of Trump is actress and comedian Rosie O'Donnell. In fact, shortly after the former "Apprentice" host was elected to a second term in office, O'Donnell made one final, dramatic act in her feud with Trump by moving to Ireland, making her one of several celebrities who left the country following Trump's win. Proving not all of Trump's enemies are from the world of politics, his feud with O'Donnell long predates his time as president. Indeed, if you only tuned into all the drama recently, you may be surprised to learn that Trump and O'Donnell have been fighting for the better part of two decades.

It all started in December 2006, an entire decade before Trump's first stint in the White House. During an episode of "The View," O'Donnell criticized Trump's response to the Miss USA 2006 controversy, brought up his alleged history of unfaithfulness in his marriages, and pushed back on Trump's image as a "self-made" man, given that his father Fred Trump was also a wealthy businessman. Trump hit back in an interview with People that same month, calling O'Donnell a "loser," mocking her weight, and even threatening legal action over her comments about Fred, as Trump claimed that he didn't inherit that much money from his father. That being said, he never actually followed through on his threats to sue.

In January 2007, shortly after the initial exchange of barbs between Donald Trump and Rosie O'Donnell, an unexpected third party inserted himself into the mix. In an apparent attempt to capitalize on all the drama, then-WWE head honcho Vince McMahon — a close friend of Trump's — booked a televised match pitting Trump against O'Donnell. Of course, the reality of the situation is that both public figures were obviously played by impersonators.

In a 2016 video chronicling Trump's on-again, off-again relationship with WWE, noted pro-wrestling commentator Brian Zane of Wrestling With Wregret noted that the segment was clearly meant to portray Trump in a much more flattering light than O'Donnell, once again mocking the comedian's weight. He also panned the whole thing as just not being very good. "Trump and Rosie had been having a war of words for some stupid reason IRL, and since Vince and Trump were friends in real life, Vince decided to give himself a laugh with this match," Zane said, adding, "But what Vince found hilarious, actual sane people thought otherwise. Simply put, this is one of the most unwatchable moments of the year — not because the people involved couldn't wrestle. Far from it. They're both legitimate workers. They guy who played Donald Trump is Ace Steel, the person who trained CM Punk. It's just this whole match was dumb. ... This match was just one big inside joke between two old rich dudes."

Suffice it to say, the real Trump and O'Donnell have remained at loggerheads ever since, and it doesn't seem like their feud will ever be resolved. Of course, with O'Donnell living in Ireland (and Trump threatening to take away her U.S. citizenship because she's a "threat to humanity"), it doesn't seem like they'll ever need to cross paths again anyway.