In June 2011, he was arrested in Santa Cruz, Bolivia, while overseeing a rice growing agricultural venture that he had invested in, and was jailed for 18 months on suspicion of money laundering, though he was never formally charged.

A group of investors, including Ostreicher and Geneva lawyer Andre Zolty, invested at least $25 million in a rice farming project in Bolivia in 2008.

The investors also state that Rodriguez became involved in a romantic and financial relationship with a drug trafficker by the name of Maximiliano Dorado.

[10] A marriage certificate showing Ostreicher was married in Bolivia was entered into evidence during the September 23 hearing.

Ostreicher appeared in a hearing on Tuesday, December 11, and the judge ordered that the case be sent back to the lower court.

[15] Fifteen people, including prosecutors, government officials, and the judge who originally had Ostreicher imprisoned, were arrested in what authorities say was an extortion ring.

On May 3, 2012, supporters of Ostreicher initiated an online petition on the White House We the People website requesting the Obama Administration to assist in the effort to free Jacob.

A total of 25,000 signatures were needed by June 2, 2012, in order to submit the petition to the White House; this requirement was met.

[28] In May 2014 Ostreicher revealed that after his release, Penn had personally nursed him back to mental and physical health at the latter's home.