The Curious Case of the Castro-Cuddling, Trump-Hating Humanitarian – The American Spectator | USA News and PoliticsThe American Spectator

Trump Derangement Syndrome claimed many casualties over the years. Big names fell like dominoes in a Hollywood earthquake. Robert De Niro morphed from a psychopathic gangster to a psychotic neighbor who threatens mailmen for delivering campaign flyers. Tom Hanks plummeted from wholesome everyman to that whiny wine mom who lectures cashiers about democracy while buying organic quinoa. Billy Joe Armstrong of Green Day devolved into a has-been punk rocker cosplaying as Che Guevara at suburban music festivals. Rosie O’Donnell, the human equivalent of a car alarm going off at 3 AM, fled to Ireland. Ellen DeGeneres ditched America for England, trading political drama for a country where the sun hasn’t been seen since the Renaissance.

But Sean Penn takes the cake… eats it, then hurls it at anyone not willing to join his moral crusade.

The recent Club Random episode with Bill Maher revealed Penn’s complete break from reality. Here’s a man who tongue-kissed every communist dictator from Havana to Caracas. Yet somehow, he developed moral qualms about his friend having dinner with a democratically elected president.

Maher, bless his cynical heart, didn’t let this slide. “Really? You’ll meet with Castro and Hugo Chávez, but not the president of the United States?” The question hung in the air like a fart in an elevator — undeniable, awkward, and reeking of hypocrisy. Penn’s moral compass doesn’t just spin wildly; it’s been replaced by a Magic 8-Ball that only gives answers like “Revolutionary Socialism” and “Orange Man Bad.”

This is, after all, the same Sean Penn who once praised Castro’s “humor” and waxed poetic about the dictator’s “affectionate tolerance” — as if gulags were just misunderstood retreats.

He’s heaped adoration on Hugo Chávez too, brushing off Venezuela’s economic implosion and descent into tyranny by insisting America was somehow worse. According to Penn, U.S. media were more propagandistic than Chávez’s state-run mouthpieces. That was his defense. (RELATED: Venezuela Follows the Classic Path of Radical Socialism)

And Trump? A different standard entirely. Penn once called him “an enemy of Americans,” suggested he might try to “destroy the world,” and urged the public to reject him like a virus. On Club Random, he practically convulsed at the notion of dining with Trump, equating the idea with spiritual contamination. No argument. No policy critique. Just disgust so intense it borders on puritanical hysteria.

This is where Trump Derangement Syndrome reaches its final evolutionary form. It’s not enough to disagree with policies or vote differently. The fully infected must construct elaborate moral hierarchies where communist butchers rank higher than Republicans. Where lunch with mass murderers is brave journalism, but dinner with Trump is collaboration with Satan’s interior decorator.

What we’re seeing isn’t political nuance; it’s theological delusion. Trump has become such a totem of evil in these circles that anyone who shook his hand is cast as ritually unclean. Meanwhile, men who jailed poets and shot dissidents get romanticized as misunderstood revolutionaries. It’s a performance of piety for a secular church that hands out indulgences to anyone who chants the right slogans. (RELATED: Why Morgan Wallen Terrifies the Left)

Penn embodies Hollywood’s complete detachment from planet Earth. He’s the guy who interviewed El Chapo while Mexican mothers prayed their children wouldn’t get beheaded by cartel members. He’s the actor who thinks memorizing lines makes him qualified to solve geopolitical crises. He’s the celebrity who confuses method acting with actual wisdom, like thinking you understand quantum physics because you played a scientist in a movie.

The syndrome manifests differently in each victim, but each response reveals the same core problem: an inability to process that maybe, just maybe, half the country isn’t comprised of fascist demons who eat babies for breakfast.

Penn’s particular strain is weapons-grade derangement. He doesn’t just hate Trump — he’s constructed an entire parallel universe where American presidents are worse than genocidal maniacs.

The Castro worship is particularly revealing. Here’s a dictator who ruled Cuba like a tropical Gulag operator. But somehow he earned Penn’s breathless admiration. Meanwhile, Trump — elected through the same democratic process that installed every other president — is literally Voldemort with a spray tan.

This isn’t principled opposition. It’s performance art disguised as morality.

The gap between Penn’s Castro-enthusiasm and Trump-hatred reveals something deeper than political disagreement. It exposes a complete rejection of American democratic legitimacy. The tragedy isn’t that celebrities have opinions. Everyone’s entitled to their delusions. The tragedy is watching allegedly intelligent people tie themselves into philosophical pretzels to justify their contradictions. Penn isn’t stupid — his brain just got hijacked by ideology and taken on a joy ride through Crazytown.

Hollywood’s Trump derangement created a generation of celebrity prophets without portfolios or prescriptions. They speak with the authority of their fame but the wisdom of their publicists. They mistake volume for virtue, intensity for insight. They’ve confused playing heroes with being heroes.

Penn, however, represents the syndrome’s peak absurdity. A celebrity so divorced from consequences that he treats international relations like casting calls for his personal revolutionary fantasy film.

The real question isn’t why Penn hates Trump — half the country does. It’s why he loves Castro more than American democracy. Hollywood elites like Penn will forgive any atrocity as long as it comes wrapped in anti-American rhetoric. They’ll excuse any oppression if it sounds sufficiently revolutionary, like calling mass murder “social justice with extreme prejudice.”

Sean Penn didn’t just lose his marbles over Trump. He gathered them up, dipped them in crazy sauce, and hurled them at anyone who dared suggest that maybe, possibly, American democracy isn’t worse than Cuban communism. The mess he left behind tells us more about celebrity culture than any sociology textbook ever could.

Sometimes the most revealing conversations happen when people accidentally expose their own insanity while thinking they’re being profound. Penn achieved that rare feat: making Bill Maher look like the reasonable one in the room.

READ MORE from John Mac Ghlionn:

America’s Dumbest Refugees Pick God’s Cruelest Joke

Soap, Sex, and Simulacra: Hollywood’s Latest Moment of Madness

Taylor Swift a Self-Made Billionaire?