When Hugh Hefner’s Playboy debuted in 1953, it drew attention for both its celebration of the female form and its attempts to fill its non-nude pages with quality short fiction and reputable journalism. The magazine's success created a new publishing genre: Salacious mainstream men’s magazines. And it didn't take long for newsstand shelves to fill up with copycats, including publisher Larry Flynt’s Hustler and Bob Guccione’s Penthouse.

But Flynt, the brash and outspoken man behind Hustler, didn’t appear to want to entertain the competition. In 1983, he allegedly plotted to have Hefner, Guccione, and others killed by a hitman.

The news, which first circulated in 1988, has received fresh attention thanks to the FBI file on Flynt recently being excavated by Vice.

According to Los Angeles County Sheriff’s Captain Robert Grimm, who held a news conference in October 1988, the murder-for-hire plot was discovered during the department’s investigation of theater producer Roy Radin’s death over a financial deal gone bad. (William Mentzer, a former bodyguard for Flynt, was one of four people charged and later convicted of Radin’s murder.) Investigators learned that in 1983, Flynt approached a man named Mitchell WerBell III and solicited his services in knocking off Hefner, Guccione, former TV Guide publisher and U.S. ambassador Walter Annenberg, and—for reasons that were never made clear—singer Frank Sinatra.

WerBell had something of a reputation as a mercenary. He claimed he had been involved as a consultant for the Green Berets and later owned a counterterrorism firm. WerBell had also been involved in developing the Ingham Model lI submachine gun. According to Grimm and Los Angeles County Sheriff Sherman Block, Flynt invited WerBell to his home and handed him a check for $1 million to knock off his targets.

The plan didn’t go very far. Flynt’s business manager stopped payment on the check just moments after WerBell left Flynt's home. But according to the recent FBI file on Flynt, WerBell’s death one month later from a heart attack raised further suspicion over the Hustler publisher. During the Radin investigation, a witness stated that a Flynt associate told him he and Flynt had drugged WerBell’s drink with heart medication. The FBI’s review of WerBell’s autopsy report failed to find anything to back up the witness’s story, though; the coroner had declared that WerBell died of congestive heart failure due to chronic pulmonary disease.

After the WerBell story first broke in 1988, Flynt flatly denied the check was intended to pay for the murders of Hefner and the others, calling it a joke. Flynt’s attorney, Alan Isaacman, said the checks were handed out to numerous people during a dinner party and weren’t meant to be cashed for any purpose. Isaacman said there was no talk of any murder. No case was ever presented to the Los Angeles district attorney’s office.

When asked to comment on the alleged plot in 1988, Guccione told the Associated Press that Flynt’s behavior was unsettling. “I think he was just a little crazy,” he said. “It was a very irrational act because neither Hefner nor I compete with his magazine ... And if you factor in Annenberg and Sinatra, it becomes even more irrational. For me, I just put it down to Flynt’s obvious dislike for me.”

Hefner passed away in 2017. Flynt died in 2019.

[h/t Vice]