How Sean Penn Orchestrated a Real-Life Prison Break

New York explores how he freed an American from Bolivia more than a decade ago
Posted Mar 22, 2026 5:31 AM CDT
How Sean Penn Orchestrated a Real-Life Prison Break
In this Dec. 11, 2012, file photo, Sean Penn pushes US businessman Jacob Ostreicher in a wheelchair during a recess at Ostreicher's hearing in Santa Cruz, Bolivia.   (AP Photo, File)

Sean Penn didn't accept his Oscar in person this year, evidently because he was on a trip to Ukraine. It was yet another reminder of the actor's forays into real-world politics, and a deeply reported story at New York magazine digs into an earlier one. The piece by Linda Burstyn details how Penn helped extract a Brooklyn businessman from Bolivia more than a decade ago. Burstyn explains how Jacob Ostreicher, a flooring salesman turned rice investor, wound up in the country's notorious Palmasola prison in 2011, accused of laundering drug money tied to a Brazilian trafficker. With Bolivia able to lock up suspects for months without charges while seizing their assets, Ostreicher says he was swept into a corrupt system that profited off his $26 million farm and his continued detention.

Enter Penn. Leveraging his connections with then-president Evo Morales, Penn managed to get Ostreicher out of prison and into house arrest—but that was only Act One. When it seemed clear that Ostreicher remained in legal trouble, Penn helped orchestrate a covert, privately funded escape run by a former Marine and "professional extractor," complete with a fake identity, cut sidelocks, and a nerve-racking border crossing to Peru. From there, Penn temporarily sheltered the shattered businessman in his Malibu home. Read the full story, which suggests that Ostreicher's freedom likely would not have happened under normal diplomatic channels, which had broken down. Instead, for better or worse, he owes his escape to a celebrity's willingness to operate in legal gray areas.

Read These Next
Get the news faster.
Tap to install our app.
X
Install the Newser News app
in two easy steps:
1. Tap in your navigation bar.
2. Tap to Add to Home Screen.

X