Robert Redford lived a life that felt like a movie script, and honestly, his relationship with Donald Trump was one of the weirder subplots. It wasn’t a friendship. It wasn't exactly a simple feud either. It was more like a long, slow-motion collision between two very different versions of the American Dream. One man built a sanctuary for independent art in the mountains of Utah; the other built gilded towers with his name on the front in Manhattan.
The world lost Redford on September 16, 2025, at the age of 89. In the wake of his passing, everyone started digging up his old quotes. People wanted to know: what did the man who played Bob Woodward in All the President’s Men—the guy who literally defined the cinematic takedown of a corrupt presidency—really think about Trump?
The answer isn't a single soundbite. It’s a journey from "I'm glad he's in there" to "monarchy in disguise."
The 2015 Confusion: "I’m Glad He’s In There"
Back in 2015, the political world was a different planet. Trump was the wildcard in the GOP primary, and Robert Redford sat down with Larry King for an interview. This is the moment Trump supporters still point to today. Redford said, "I'm glad he's in there because him being the way he is... I think shakes things up and I think that's very needed."
Trump, never one to miss a compliment, immediately blasted that quote on Twitter (now X). "Wow! Such nice words from Robert Redford," he wrote.
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But there was a catch. Trump had cut off the first part of the sentence.
Before the "shake things up" comment, Redford had actually told King, "He's got such a big foot in his mouth, I'm not sure you're going to get it out." Redford wasn't endorsing the man's platform; he was enjoying the spectacle. He was a storyteller watching a character wreck a "bland" and "boring" political system. A spokesperson for Redford eventually had to clarify that while Robert enjoyed the "entertainment value," he wasn't supporting Trump for president.
The Shift to Alarm: "A Monarchy in Disguise"
By the time 2019 rolled around, the amusement had evaporated. Redford wasn't laughing anymore. In a blistering op-ed for NBC News’s THINK platform, he basically laid out his "breakup" with the administration. He admitted he’d wanted to give the guy a chance, but said he was "disappointed" and then "alarmed" by what he saw.
He didn't hold back. He called the administration a "monarchy in disguise" and a "dictator-like attack on everything this country stands for."
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Think about that for a second. This is the guy who spent his career playing the ultimate American heroes—the Sundance Kid, the principled journalist, the naturalist. To him, the "Divided States of America" (his words) was a personal tragedy. He felt the country had lost its moral compass.
Redford's primary gripes weren't just about personality. They were about the things he spent his life defending:
- The Environment: Redford was a trustee of the Natural Resources Defense Council (NRDC) for decades. Seeing environmental protections rolled back felt like a punch to the gut.
- The Arts: He famously worried about the elimination of the National Endowment for the Arts (NEA), something he discussed at the 2017 Sundance Film Festival.
- The Truth: Having lived in the shoes of Bob Woodward for a movie, the "fake news" era didn't sit well with him.
The 2020 Endorsement and the "Fault Lines"
In 2020, Redford went all in for Joe Biden. He wrote another piece, this time for CNN, where he dropped a quote that has since become famous. He wrote that Trump didn't create the divisions in America, but he "found every fault line in America and wrenched them wide open."
It’s a nuanced take. He wasn't blaming one man for every problem in the U.S., but he was blaming him for making the cracks deeper. Redford's politics were always about conservation—conserving the land, conserving the truth, and conserving a certain level of civility. He felt that the Trump era was the opposite of conservation. It was demolition.
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Trump’s Surprising Final Word
When Robert Redford passed away in September 2025, things took a weird turn. Given their history, you might have expected silence or a "nasty" comment from the former president. Instead, Trump spoke to reporters on the South Lawn and said, "Robert Redford was great."
It was a classic Trump move—praising a legend even if that legend spent his final years calling you a dictator. Maybe it was respect for Redford's "star power," or maybe it was just the fact that in the end, both men understood the power of a great image.
What We Can Learn From the Redford-Trump Dynamic
Looking back, the "Robert Redford on Donald Trump" saga is a lesson in how Hollywood and Washington interact. Redford wasn't just another "liberal actor" shouting into the void. He was a guy who actually built something—the Sundance Institute—that changed the culture. When he spoke, he spoke from a place of having skin in the game.
If you're trying to make sense of the modern political divide, Redford’s evolution is a pretty good roadmap. He started with a curiosity about "shaking up the system" and ended with a plea for "civility and progress."
Actionable Insights for Navigating Political Celebrity Culture:
- Check the Full Quote: Like the 2015 Larry King interview showed, a ten-second clip can be the opposite of the truth. Always look for the "but" or the context before the comma.
- Look for the "Why": Redford’s issues with Trump weren't just about tweets; they were about the NRDC, the NEA, and the Sundance Institute. Understanding a celebrity's actual work helps you understand their political stance.
- Recognize the "Pendulum": As Redford said at Sundance 2017, "Presidents come and go, the pendulum swings back and forth." He stayed focused on his work (storytelling) even when he was unhappy with the government.
- Vote Your Values: Redford's ultimate message in every op-ed was the same: stop waiting for a "special counsel" or a miracle. Use the "power of your vote."
Robert Redford didn't want people to just listen to him because he was a movie star. He wanted people to look at the "fault lines" and try to heal them. Whether you agreed with his politics or not, his consistency on the environment and the arts over sixty years is something you don't see much of anymore. He was a man of the mountains, and from his view, the political landscape looked like it needed a lot of conservation.