Actor Sean Penn said he felt “conned” by Russian President Vladimir Putin after a 2001 dinner that he recounted Thursday on "Jimmy Kimmel Live!", drawing a comparison to President Donald Trump’s recent interactions with the Russian leader.
Penn said he and Jack Nicholson met Putin while attending the Moscow Film Festival to promote Penn’s film "The Pledge." A photo produced on the show showed the two actors seated at a table with Putin. Penn said the meeting occurred "two to three weeks after then-President [George W.] Bush said, 'I looked into his eyes and I felt I could trust him.'" Penn added, "I have to say, when I say that, I was conned also. I felt that there was something genuine there."
Pivoting to Russia’s invasion of Ukraine, Penn described actions by the Kremlin he said had shown Putin’s true nature. "Now we know that he’s very willing to kidnap 30,000 kids, murder a lot of people ... and teach those kids to hate their parents and their country," Penn told host Jimmy Kimmel. He criticized the United States for not being sufficiently united to provide Ukraine with the resources he said are needed to defeat Putin.
Penn’s recollection of feeling deceived echoes comments by Trump, who has publicly described being on friendly terms with Putin even as the war in Ukraine continued. "I speak to him a lot about getting this thing done, and I always hang up and say, well, that was a nice phone call, and then missiles launched into Kyiv or some other city," Trump said, acknowledging that cordial conversations did not prevent military actions.
Critics of Trump’s approach to Putin have argued that the U.S. president has been used for propaganda gains by the Russian leader. Sen. Chris Van Hollen, D-Md., wrote on X that Putin "got a meeting on U.S. soil, Trump got flattered by Putin. Advantage Putin. Shameful." French President Emmanuel Macron has also said recent interactions reflected a pattern in which "President Putin played President Trump."
Observers note a series of missed or expired diplomatic deadlines and high-profile meetings, including a summit in Alaska, that opponents say have been exploited by the Kremlin as photo opportunities or tactical gains rather than steps toward lasting de-escalation. Supporters of engagement have argued that dialogue remains necessary to reduce risks and protect civilians; critics say personal diplomacy has at times obscured Russian aggression.
Penn, an Oscar-winning actor who also has worked as a director and humanitarian activist, framed his memory of the Moscow dinner as part of a larger warning about underestimating the Kremlin. His comments add a cultural and personal dimension to an ongoing debate in Washington and among NATO allies over how best to respond to the war in Ukraine and whether current levels and types of support are sufficient.
The exchange on Kimmel came as U.S. lawmakers, European leaders and Ukraine’s allies continue to weigh military, economic and humanitarian assistance to Kyiv while assessing Moscow’s tactics on and off the battlefield. Penn’s remarks underline how firsthand encounters with world leaders can shape public perceptions as policymakers consider future steps in the conflict.