The Federal Bureau of Investigation staked out the Chicago apartment of Playboy founder Hugh Hefner over two months during an investigation — and found the notorious hedonist only walked three blocks for a lonely dinner and then turned in early for the night, according to newly released documents.

The FBI’s case files on Hefner, who died in 2017, and the bureau’s investigation into obscenity accusations against him, were released this week as documents of “public interest and historical value.”

The 58 pages of documents, many significantly redacted of names and details, date back to 1956, three years after the launch of the magazine amid controversy over its unabashed presentation of female nudity.

The tipster said Hefner hosted ‘frequent late hour parties’

The files document a canny interview agents had with Hefner in the late 1950s after he learned of their secret probe and boldly invited them into his office.

At first, the FBI simply monitored the magazine’s 1953 launch, and various controversies over its content and distribution, through news clippings that describe Playboy as “oversexed,” “vulgar” and “obscene.”

The bureau’s first investigation into Hefner, however, was not about the contents of the magazine but for something he was suspected of doing using the magazine’s fame as cover. An investigation in 1958 into Hefner and a freelance photographer suspected they were engaged in “interstate transportation of obscene matter,” the files say.

The probe began after a tip to the bureau’s Chicago office, but the tipster’s identity was redacted from the files before their release.

Hefner and Edward Zukor Oppman, the documents say, were suspected of “producing nude photographs made of young models who pose thinking their photographs are to appear in ‘Playboy’ Magazine or used for modeling purposes.” There are later references to the production of “stag film” and the “sales or distribution of obscene matter.”

The tipster said Hefner hosted “frequent late hour parties” in Chicago. The parties were “almost on a weekly basis” and “sometimes last through the night.”

Agents interviewed several people who knew Hefner and Oppman, including a former Playboy employee who left the magazine because his salary was too low and “he did not approve of Hefner’s moral character.”

“He said that Hefner drinks excessively and conducts parties in his apartment,” the agents note. Even so, he didn’t think Hefner was violating any laws.

Another interviewee said Hefner “ran around with other women,” but to her knowledge, he was not involved in “obscene matters or prostitution” and said he was “too clever a man to knowingly violate a local or federal law.”

The probe seemed to focus more on Oppman than Hefner. Oppman, a former photographer with the U.S. military’s 8th Airborne Division during the Second World War, had a previous conviction for “contributing to delinquency of a minor,” the files say.

The FBI chased leads in Tennessee, Florida, Texas, Illinois and Mississippi.

Agents were instructed to put Hefner’s apartment under surveillance, “particularly in the evening hours.”

For seven nights, Special Agent Harold Brown staked out Hefner’s place at 232 East Ohio St., Chicago.

On May 13, 1958, Brown noted in his report, Hefner emerge at about 6:45 p.m. and walked three blocks to a restaurant where he ate dinner and then returned and turned off his apartment lights for the night. No other activity from his surveillance is noted.

Agents also hunted down people who knew Oppman. Most said they knew nothing about illegal photos and knew him as a legitimate photographer taking portraits of prominent people, including a court judge. He was a “flop” in business and poor at repaying debts, people said, but not a known deviant.

A former news correspondent who knew the photographer from the war, said Oppman occasionally took nude or semi-nude photos of models but nothing illegal. Once, the writer said, Oppman willingly turned over nude photos of a model who had gone on to become famous. The woman’s name is redacted from the file.

Agents got a first-hand look at the contention that Hefner was “too clever” for them. Hefner was tipped off to the FBI’s probe and called Brown directly. Hefner said he had been told “the FBI has been making inquiries about his activities” and invited them in to interview him, Brown wrote in a report.

On June 3, 1958, Brown and another agent went to the Playboy office to speak with him.

Hefner told agents about the magazine’s start and moving to its new location, that housed both the editorial offices and his apartment. He said the owner refused to sell it to him and he had repeated arguments with a landlord, who disconnected his lights, kept reporting him to the Chicago police and even hired a private eye to investigate what he was doing in an attempt to “build up to eviction” of Playboy from the building.

(Although the file does not say, there is a suggestion the landlord may have been the FBI’s original tipster.)

Hefner said he has never taken any movie or film that would not pass the censorship regulations and all of his film was processed openly through Eastman Kodak. He said Playboy is “edited to appeal to men and has a number of pin-up type and art type photographs.”

The file says: “Hefner stated that he has been accused of having wild parties in the offices of ‘Playboy’ but he emphatically denied any party activities at this address and stated that he occupies sleeping quarters at the rear of his office on the 4th floor.”

Hefner employed a number of “young girls” at the magazine but refrained from being “intimate” with them as it would “cast a bad reflection” on the magazine. He said he was separated from his wife but that was a personal matter.

He said Playboy was comparable to Esquire magazine (where he once worked) but “has a wider circulation.”

Hefner told the agents he first met Oppman when the photographer sent him photos he took of a woman who Hefner then featured in the magazine.

Hefner agreed that Oppman “would be the type of individual who might become involved in obscene matters,” the file says, and he has since severed his ties to him because he found out he had a criminal record.

The agents’ investigation, the case notes concluded in July 1958, “fails to reflect a violation” of federal laws dealing with obscenity.

Hefner and Playboy again came to the FBI’s official attention in 1963.

A memo sent to J. Edgar Hoover, director of the FBI, from the Special Agent in Charge of the bureau’s Chicago office, dated June 4, 1963, states: “Enclosed herewith is one copy of the June issue of Playboy Magazine and one newspaper clipping from the Chicago Tribune.”

The issue featured a provocative photo spread of American movie actor Jayne Mansfield and the news column described the pictorial as “coarse, cheap, vulgar, utterly without taste.”

The issue led to Hefner’s arrest in Chicago on state charges for obscenity. The Chicago office flagged the magazine’s nationwide circulation as possibly making it a federal matter.

An internal discussion in Washington branded the charge “ridiculous,” but the Chicago office was told to keep an eye on how the prosecution unfolded. A jury later was unable to reach a verdict, a follow-up note says.

The FBI’s files were then silent on Hefner, according to the records released, until 2001 when agents again interviewed him, this time as a complainant rather than suspect.

Someone had hacked into Hefner’s Playboy email account and was sending out emails — 15,000 to 16,000 of them — from his personal account of hef@playboy.com and other spoofed accounts in his name.

The nature of the emails are redacted from the files. Playboy officials told the FBI that messages alerting recipients to the intrusion had now been sent and a private security audit was underway.

There is no follow up noted.

The FBI routinely releases redacted files on prominent people after they die.

The FBI said these releases “may no longer reflect the current beliefs, positions, opinions or policies” of the bureau.

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