Jonathan Pollard pleads guilty to espionage for selling top-secret U.S. military intelligence information to Israel. The former Navy intelligence analyst sold enough classified documents to fill a medium-sized room.

Pollard was arrested in November 1985 after authorities learned that he had been meeting with Israeli agents every two weeks for the last year. He was paid approximately $50,000 for the highly sensitive documents and expected to receive as much as $300,000 in a secret Swiss bank account. The top-secret information included satellite photos and data on Soviet weapons.

Pollard was sentenced to life in prison while his wife Anne received a five-year sentence for being an accessory to the crimes. The discovery of his betrayal put a chill on the relationship between the U.S. and Israel. Viewing the U.S. as its ally, Israel believed that the information should have been passed along anyway. But the fact that some Israeli agents remained in high positions despite their involvement in the espionage angered the United States.

Israel has since stuck by Pollard. During peace negotiations mediated by President Clinton in the late 1990s, the nation made Pollard’s release from prison a key point. Though Israel continues to work toward Pollard’s release, the United States has declined to work out such a deal.