Love him or hate him, Donald Trump will always be a curious figure in American politics. That’s because well before he decided to become a politician, Trump was a famous real estate guy turned TV celebrity. Between schmoozing around New York and Hollywood, he gathered support from a number of famous friends.
Over the years, these friends supported Trump…right up until they didn’t. Time after time, these celebs would reach a breaking point listening to Trump’s rhetoric before making a public break with him.
Which celebs are we talking about, and what do they have to say about the man they used to support? Keep reading to find out!
You would expect a lot of common ground between Arnold Schwarzenegger and Donald Trump. After all, each man knows what it is like to leverage celebrity into political power. And Schwarzenegger is a former Republican governor who has voted for conservatives ever since 1983.
However, the two have a weird history of (mostly one-sided) feuding that began after Schwarzenegger took over as the celebrity host of The Apprentice, causing Trump to take to Twitter and complain about how he did a much better job than Arnold. Later, Arnold hit back in March 2017, taking to Twitter to criticize Trump’s low approval ratings.
Publicly, though, the earlier breaking point was the release of the infamous Access Hollywood tape where Trump brags about sexually assaulting women. This caused Schwarzenegger to share with Twitter that he would emphatically not be voting for Trump.
Over the years, Kanye West has been a one-man political compass. He shocked many fans a few years ago by supporting Donald Trump’s 2016 election. This resulted in Trump inviting Ye to the White House to discuss cultural issues. Over the next few years, West mostly supported Trump by praising him on Twitter, though he curiously deleted his pro-Trump tweets from before December 2016.
Eventually, Kanye gave an interview with Forbes where he formally broke with Trump. In an evocative metaphor, he told the interviewer he was “taking the red hat off, with this interview.” Though whether this is due to Kanye having a change of heart or just developing presidential aspirations of his own, we may never know.
Tom Brady was put in a more difficult spot by Trump’s politics than most of his famous supporters. That’s because Brady wasn’t just a famous Trump supporter: he was also a longtime golfing buddy of the president.
Previously, ESPN reported that Brady had a MAGA hat in his locker that he called “a nice keepsake,” and he supported Trump becoming president. After Trump went off online about kneeling football players, Brady did not show up to the White House after the Patriots won the Super Bowl.
He claimed at the time it was because of personal family issues. According to TMZ, he later shared his real thoughts on Trump’s divisive arguments in a radio interview, saying, “I just want to support my teammates and … I do believe in what I believe in, and I believe in bringing people together and respect and love and trust, and those are the values that my parents instilled in me.”
Bryan Cranston is a perfect example of moderate support for Trump. While he didn’t vote for Trump as president in 2016, Cranston publicly denounced the Trump critics rooting for the man to fail. As he told The Hollywood Reporter, “If [Trump] fails, the country is in jeopardy. It would be egotistical for anyone to say, ‘I hope he fails.’ To that person I would say, f**k you. Why would you want that? So you can be right? I don’t want him to fail. I want him to succeed. I do. I honestly do.”
Impressively, Cranston kept traveling this moral high road for most of Trump’s presidency. However, Trump’s claims in 2020 about treating COVID-19 with disinfectants pushed Cranston over the edge. He took to Twitter to declare, “I’ve stopped worrying about the president’s sanity. He’s not sane. And the realization of his illness doesn’t fill me with anger, but with profound sadness. What I now worry about is the sanity of anyone who can still support this deeply troubled man to lead our country.”
Watching Dave Chappelle’s public statements and comments on Donald Trump is a bit like watching a rollercoaster traveling up and down. It all started with a standup routine Chappelle performed at New York’s The Cutting Room after the 2016 presidential election. The routine was not recorded, and even though Chapelle later claimed he was mocking both Trump and Clinton, the local paper The Observer reported that his tone that night was decidedly pro-Trump.
This caused Chappelle to issue a statement about how disgusted the election made him and about how he didn’t want anybody to think his comedy was defending Trump. Nonetheless, when Chapelle hosted Saturday Night Live the next week, he took a moral high road and shocked countless fans by saying “I’m wishing Donald Trump luck, and I’m going to give him a chance, and we the historically disenfranchised demand that he give us one too.”
A few months later, Chapelle expressed serious regret for those words. As reported by The Hollywood Reporter, he was at a Robin Hood New York City in May 2017 and said “I was the first guy on TV to say ‘Give Trump a chance.’ I f*ked up. Sorry.”
Jesse Ventura has something more in common with Arnold Schwarzenegger than starring in Predator and then going on to become a governor. And that final commonality is this: each man previously supported Trump and went on to regret it.
Historically, Ventura has been very critical of both Democrats and Republicans. This may explain why he successfully ran for governor of Minnesota as part of the Reform Party. This may be why he initially liked Trump as a presidential candidate: CNN reports that he openly praised Trump, possibly in an attempt to get chosen as a vice presidential candidate. And Ventura went on to write an article for Time praising Trump’s ability to destroy the GOP.
While Ventura said nice things about Trump before, he now hates being compared to the man. He said so in an interview with MPR News, saying the comparisons are “hogwash.” And his former Chief of Staff Steven Bosacker took things a step further by illuminating how Ventura is different from Trump: “Jesse Ventura is colorful. He’s not corrupt.”