A jaw-dropping Hollywood rescue mission is making headlines years later—and Sean Penn is at the center of it.
According to a gripping feature published by New York Magazine, the Oscar-winning actor played a pivotal role in freeing New York businessman Jacob Ostreicher from a brutal Bolivian prison in the early 2010s. Ostreicher, a Hasidic investor, had poured money into a rice farming venture in Bolivia when he was suddenly swept up in a money-laundering investigation tied to a Brazilian drug trafficker. He was held for months without formal charges inside a notoriously dangerous prison, where he reportedly endured beatings, hunger strikes, and paid other inmates for protection.
Desperate and fearing for his life, Ostreicher was told by fellow prisoners that only then-President Evo Morales could help him—but Morales had a strained relationship with the United States. Inmates believed Sean Penn, who had previously worked alongside Morales’ ally Hugo Chávez on Haiti earthquake relief efforts, might be the one American with enough influence to intervene. After failed attempts to contact him, Penn ultimately learned of Ostreicher’s situation through a surprising chain of events involving Mark Wahlberg’s bodyguard and an episode of ABC’s Nightline.
Ostreicher later recalled the surreal moment Penn appeared at his cell door, describing him as looking “like the Messiah with a tan.” Using diplomacy—and even leveraging Bolivia’s passion for soccer—Penn reportedly met directly with Morales. The talks led to Ostreicher being transferred to a hospital and eventually placed under house arrest.
What happened next sounds straight out of a movie script. When legal efforts stalled, Penn allegedly orchestrated a covert escape plan, disguising Ostreicher and arranging overland travel into Peru with altered documents. From there, Ostreicher flew to Los Angeles, where he stayed at Penn’s home. Hollywood heavyweights Robert Downey Jr. and Danny Trejo are said to have helped him adjust to life back in the U.S. after the ordeal.
