Sean Penn’s Crusade: Why He’s Risking It All for Ukraine, Furious at Will Smith and Ready to Call Bulls— on Studios’ AI Proposals

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Sean Penn’s Crusade: Why He’s Risking It All for Ukraine, Furious at Will Smith and Ready to Call Bulls— on Studios’ AI Proposals
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Summer light fades to gold in Malibu. Surfers carve tasty waves just down the road. A beautiful woman wanders toward the pool house. She crosses paths with a sweet dog heading the opposite way look…

Summer light fades to gold in Malibu. Surfers carve tasty waves just down the road. A beautiful woman wanders toward the pool house. She crosses paths with a sweet dog heading the opposite way looking for an ear rub.’s house. Small talk is made about how the coffee table in his living room looks like a junk drawer just exploded on it. There are sunglasses, prescription bottles and a device that shoots salt at mosquitoes. Nearby are photos of famous people, all smoking.

Penn tells me he became convinced his only choice was to destroy his Oscars. “I thought, well, fuck, you know? I’ll give them to Ukraine. They can be melted down to bullets they can shoot at the Russians.” Running on a semi-parallel path has been Penn’s political work. It first surfaced in 2002 when he flew to Baghdad and called bullshit on George Bush’s claim that Iraq had weapons of mass destruction. He correctly predicted the terrible cost of American boys going to fight ghosts in the desert, earning him many foes in the freedom fries caucus.

Sometimes it’s not clear what role Penn is playing as he appears live from this year’s hot spot: Journalist? Activist? Global gadfly? Penn says he’s not a journalist — he wryly offers in “Superpower” that he’s no Walter Cronkite — but merely a concerned citizen who knows his celebrity status can provide him an all-access lanyard to international actors.

“After the Arab Spring, all the pundits were saying, ‘He’s gone in 30 days — it’s over,”’ says Penn. “And now it’s five years later. How’d that happen? Aleppo is on fire. What’s going on?” Penn busied himself with more morally substantial work. In 2019, he converted his Haitian relief organization into the Community Organized Relief Effort, a global disaster relief group. He begged and wheedled the well-heeled in Hollywood for donations, often resulting in angry frustration. Meanwhile, his film career had ground to a halt except for a voiceover in “Angry Birds” and a film with angry man Mel Gibson — 2019’s ill-fated “The Professor and the Madman.

The footage is remarkable. It is Feb. 24, 2022, and Russian troops have invaded Ukraine. Tanks cross the border, missiles slam into Kyiv and paratroopers are landing at the airport. Millions of refugees begin streaming westward. According to Penn, any thought of meeting with Zelenskyy on the 2021 trip was scuttled by a lockdown of his government after a purported intelligence leak to the Wagner Group, mercenaries allied with Russia.

A get-acquainted meeting was set for Feb. 23, what turned out to be the eve of the invasion. Penn had one stipulation: The initial encounter would not be filmed. “I wanted him to be able to decide if we could build trust, and you can’t do that with cameras rolling.” “My biggest concern at the time was that Sean was with Zelenskyy,” O’Brien says, “and I assumed the Russians were going to try a decapitation strike and take Zelenskyy out. I didn’t want Sean in the bunker when it got hit by a missile.”

“I saw a very big change in him from one day to the next,” says Penn. “At that moment, he was the significant target. But he wasn’t going anywhere. That day, he found out that he was born for this.” “When you step into a country of incredible unity, you realize what we’ve all been missing,” he said to Hannity. It was a common Penn sentiment that echoed his thoughts on Haiti: “There is a strength of character in the people who have, by and large, never experienced comfort. That’s exactly the character that our Main Street culture lacks and needs in the United States.” Both are noble statements that oddly suggest what America needs for unity is an apocalyptic event.

“Don’t encourage these Ukrainians or support them to win this thing we all say we stand for because you might create problems for us that are nuclear,” says Penn with exasperation, paraphrasing the critic. He ushers in his second unfortunate analogy of our near three-hour conversation. “It’s saying, ‘OK, I’ll be your bitch. You want my daughter as your sex slave?’”Eric Ray Davidson for Variety

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