Playboy magazine was founded just a few years after Central Intelligence Agency, and together, those two institutions left their mark on the 20th century, for better and for much, much worse. To mark Hugh Hefner’s passing, we dug up those times those two overlapped in the Agency’s declassified archives.

While popular media has often portrayed Jim Garrison, the New Orleans District Attorney behind the infamous Clay Shaw trial, as having been targeted by the federal government for retribution, a look at his FBI file reveals the exact opposite - according to the documents, Garrison’s investigation was considered so toxic and aggressive that Director J. Edgar Hoover ordered no agents have any contact with him. When third parties began providing the FBI with evidence that Garrison had engaged in fraud against the government, the Bureau cautioned against investigating him, precisely because of how Garrison would inevitably frame it.