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The Wild Story Of How Sean Penn Helped A U.S. Businessman Out Of A Hellhole Prison

Lee Moran
Updated
2 min read

The extraordinary story of how Oscar winner Sean Penn in the early 2010s helped engineer the escape of New York Hasidic businessman Jacob Ostreicher from a Bolivian hellhole prison ― and how Hollywood stars Robert Downey Jr. and Danny Trejo helped the recently freed man readjust to life ― is detailed in a sweeping new feature published Tuesday  by New York Magazine .

Ostreicher had invested in a rice farm in Bolivia when he became entangled in a money-laundering investigation linked to a Brazilian drug trafficker. Held without charge, he spent months inside a notorious prison, where he feared for his life, endured beatings, went on a hunger strike and paid another inmate for protection.

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Read the full story at New York Magazine .

Fellow prisoners suggested his only hope was intervention from then-Bolivian President Evo Morales, despite Morales' hostility toward the United States.

Jacob Ostreicher (right) and Sean Penn, pictured in 2012.

Jacob Ostreicher (right) and Sean Penn, pictured in 2012. AFP via Getty Images

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According to the feature, inmates said the only American with enough influence to assist could be Penn, who had previously, controversially, struck up an association with Morales' ally, the late Venezuelan President Hugo Chávez, following their work together on earthquake relief in Haiti.

Early attempts to reach Penn failed. But word soon reached Penn via fellow actor Mark Wahlberg's bodyguard and an ABC "Nightline" episode.

Ostreicher recalled how one day there was a knock on his cell door, which he opened to see Sean Penn, "looking like the Messiah with a tan."

Sean Penn in 2012 talking with Bolivia's then-President Evo Morales.

Sean Penn in 2012 talking with Bolivia's then-President Evo Morales. via Associated Press

Penn lobbied Morales directly, via some soccer diplomacy, and secured Ostreicher's transfer to a hospital, followed by house arrest.

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Ostreicher's initial reluctance to flee, and instead seek justice, changed when Penn agreed to play him in a movie of the events.

From there, the actor orchestrated Ostreicher's smuggling overland into Peru using a disguise and an altered passport before flying him to Los Angeles where Ostreicher stayed at Penn's home and received support from Trejo and Downey Jr.

U.S. Updates

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