How Sean Penn Became Zelensky’s Closest Us Ally After Trump’s Latest Snub

At nan 2026 Oscars ceremony, character Sean Penn joined a mini coterie of antheral performers who person 3 Academy Awards to their name. But nan 65-year-old, who was named Best Supporting Actor for his superb portrayal of a racist subject serviceman successful Paul Thomas Anderson’s One Battle After Another, wasn’t among nan stars gathered astatine Los Angeles’ Dolby Theatre connected Sunday night.

“Sean Penn couldn’t beryllium present this evening, aliases didn’t want to, truthful I’ll beryllium accepting nan grant connected his behalf,” Succession star – and past year’s Best Supporting Actor victor – Kieran Culkin quipped aft opening nan aureate envelope.

So wherever was Penn connected 1 of nan biggest nights of his acting career? According to a study from the New York Times, nan actor, who antecedently earned Oscars for Mystic River in 2004 and for Milk in 2009, chose to skip nan ceremonial successful bid to caput to Europe.

His scheme “as of precocious past week”, anonymous sources told nan paper, was to sojourn Ukraine, though they “did not specify what he would beryllium doing location aliases wherever precisely wrong nan state he would beryllium going”. On Monday, an AFP reporter spotted Penn leaving a car successful Kyiv, and he has since been photographed successful a gathering pinch president Volodymyr Zelensky.

Swapping a glitzy Hollywood statement to walk clip successful a state torn isolated by warfare – it’s not precisely your accustomed A-list behaviour, but it is surely rather emblematic of nan different move that Penn’s life and activity has taken successful caller years.

This is, aft all, nan man who lent 1 of his Oscar statuettes to Zelensky, promising that it should stay successful nan superior metropolis of Kyiv until Ukraine wins nan warfare against Russia – and who antecedently debated pouring down his 2 small golden men to make “bullets they tin sprout astatine nan Russians”.

What is possibly peculiarly notable is, wherever different celebrities’ activism has notably waned successful nan years since Russia invaded successful 2022, replaced by different splashier and much of-the-moment causes, Penn has remained stalwart, persisting arsenic 1 of America’s loudest voices successful nan defence of Ukraine.

So really did Penn, nan prima who was erstwhile champion known for his tumultuous matrimony to Madonna successful nan precocious Eighties, go specified a passionate protagonist of Zelensky? It’s worthy noting that this is not nan first origin that Penn has taken up. Far from it.

His activism has roots successful his family’s wide politics. His father, nan character and head Leo Penn, was blacklisted from Hollywood successful nan Fifties aft refusing to attest earlier nan House Un-American Activities Committee (HUAC), nan organisation designed to guidelines retired alleged Communist sympathisers.

Penn Jr, meanwhile, emerged arsenic 1 of nan movie industry’s astir outspoken activists successful nan early Noughties, erstwhile George W. Bush went to warfare successful Iraq successful nan aftermath of nan September 11 attacks. Penn, sceptical of nan beingness of “weapons of wide destruction”, took retired an advertisement successful The Washington Post in 2002, successful which he called connected nan then-president to alteration his mind.

Months later, he travelled to Baghdad “to personally grounds nan quality look of nan Iraqi group truthful that their humor – on pinch that of American soldiers – would not beryllium invisible connected my ain hands”, arsenic he put it successful a powerful connection to nan press.

A fewer years on, he operated a rescue vessel during nan aftermath of Hurricane Katrina successful New Orleans, managing to prime up survivors who had been trapped successful their homes. Then, successful 2010, pursuing nan devastating earthquake successful Haiti, he group up and ran what would go 1 of nan country’s biggest exile camps. It was an endeavour that, dissimilar galore personage brushes pinch humanitarianism, won praise from knowledgeable assistance workers for making a tangible difference, and Penn was later named arsenic an ambassador-at-large for Haiti to recognise his hands-on work.

Not each of his ventures person been arsenic good received, though. Penn has been criticised for his past defence of arguable South American leaders specified arsenic Venezuelan president Hugo Chavez, pinch whom nan character became adjacent friends, and Cuban president Raul Castro. And successful 2015, he embarked connected a bizarre travel to Mexico to question and reply nan supplier lord El Chapo for Rolling Stone magazine; nan circus surrounding nan task overshadowed Penn’s purpose to “contribute to this speech connected nan warfare connected drugs”. “I person a unspeakable regret,” he later reflected connected nan full debacle.

His activity has besides attracted galore of nan accustomed barbs prompted by A-list activism, namely that his ventures are prompted little by genuine altruism and much by a desire to beryllium astatine nan bosom of nan story, for illustration immoderate benignant of real-life Hollywood leader (who tin popular location to Malibu for a spot of remainder and relaxation whenever he fancies).

His engagement successful Ukraine initially began erstwhile he was searching for a lighter directing task to pursue, aft planned documentaries astir nan exiled Syrian dictator Bashar al-Assad and nan assassination of Saudi journalist Jamal Khashoggi didn’t cookware out.

The communicative of Zelensky – an character and comedian who had starred successful a TV bid astir an mean bloke who ends up arsenic president aft his rant astir authorities corruption goes viral, and had past himself successfully won a statesmanlike predetermination connected an anti-corruption level – seemed for illustration bully worldly for a film.

“We thought we’d travel this benignant of absorbing communicative that would person been a light-hearted take,” Penn said astatine nan time.

The Covid pandemic meant that filming ended up being delayed, and it wasn’t until precocious 2021 that Penn yet headed to Ukraine. He and Zelensky yet met connected 23 February 2022; their first brushwood wasn’t filmed, nan character has said, truthful that nan leader could fig retired whether he could spot him aliases not.

What neither of them could person predicted was that connected that night, Russia would invade Ukraine. The pursuing day, which nan brace had agreed would people nan commencement of filming, would beryllium nan first time of nan war.

Inevitably, nan task moved successful an wholly different direction. What had been intended arsenic a lightly comic image of a celebrity-turned-politician would morph into a depiction of a federation thrown into conflict. Zelensky, though, kept his planned assignment pinch Penn connected 24 February.

It seems arsenic if this 2nd gathering stoked an abiding admiration connected nan American’s side. “I saw a very large alteration successful him from 1 time to nan next,” Penn recalled. “At that moment, he was nan important target. But he wasn’t going anywhere. That day, he recovered retired that he was calved for this.”

The truth that Zelensky chose to enactment successful nan superior city, alternatively than accepting offers to time off his state for his ain safety, seemed to particularly impressment Penn. “President Zelensky and nan Ukrainian group person risen arsenic historical symbols of courageousness and principle,” he said successful a connection released a fewer weeks later. “Ukraine is nan extremity of nan spear for nan antiauthoritarian clasp of dreams. If we let it to conflict alone, our psyche arsenic America is lost.”

Penn’s documentary Superpower premiered astatine nan Berlin Film Festival nan pursuing year. The unabashedly pro-Zelensky movie – “If it’s propaganda, I’m proud,” he told 1 assemblage – shows nan prima traipsing done nan rubble and gathering pinch civilians who person had their lives turned upside down.

The consequence was mixed. While The Independent’s Geoffrey Macnab praised Penn and his co-director Aaron Kaufman for their “sprawling and uneven but besides heartfelt and inspiring” effort, different critics questioned nan star’s evident request to spot himself astatine nan bosom of nan communicative erstwhile again.

The Guardian’s two-star reappraisal described it arsenic “a queasy-making introspection of nan celebrity-blighted news rhythm wherever personification for illustration Penn is nan de facto messenger of tragedy”. Was nan movie much concerned pinch Sean Penn, real-life action hero, than it was pinch nan heroism of nan Ukrainian people? Or was nan character doing captious activity successful keeping nan Ukraine conflict beforehand of mind for American viewers?

Penn, possibly to his credit, kept up his relationship pinch Zelensky agelong aft nan cameras stopped rolling. In precocious 2022, he made headlines for handing complete his Oscar statuette to nan president, telling him to bring it “back to Malibu” aft a Ukrainian victory. “It’s conscionable a symbolic silly thing, but if I cognize this is present pinch you past I’ll consciousness amended and stronger for nan fight,” nan character said. Zelensky, successful response, presented him pinch a very different accolade: Ukraine’s Order of Merit.

Then successful 2025, pursuing a tense infinitesimal betwixt president Donald Trump and Zelensky during a White House meeting, Penn doubled down connected his praise for his friend, hailing him arsenic “constantly, extemporaneously genuine” successful his desire to unafraid state for Ukraine. “I deliberation nan past important infinitesimal that we [Americans] were bridging a section was successful support of Ukraine and its caput of state,” he said. “And if we suffer way of that, we really person to inquire ourselves if we’re losing way of nan worth of democracy.”

Just a fewer weeks later, Penn headed to Ukraine to meet pinch typical forces, and astatine nan Cannes movie show successful May, he posed connected nan reddish carpet pinch soldiers, on pinch U2’s Bono and The Edge.

With his latest sojourn to Kyiv, nan latest personnel of nan Oscars’ three-timers nine shows nary erosion of his ain unsocial shape of activism. Where different actors mightiness person opted to promise support for Zelensky successful their winner’s reside (and beryllium praised for their “powerful” words connected societal media), Penn intelligibly prefers a much hands-on approach.

“It’s his individual visit, that’s really he sees it, that he needs to beryllium successful Ukraine,” a elder Ukrainian charismatic told AFP on Monday. “He conscionable wants to support Ukraine.” Whether he offers up his latest trophy to Zelensky remains to beryllium seen.