During his lifetime, Playboy publisher Hugh Hefner was said to have beded thousands of beautiful women. However, for the most part, the cultural icon was fairly quiet about the details about what went down in the Playboy Mansion. However, what if we were to tell you that Hefner kept a collection of some of his most scandalous memories? Well, it turns out this story is confirmed to be 100% true. Take a look at the gallery below to learn how Hefner went from husband to hustler and back again—then let us know what you think he kept to remember some of his wildest nights in the comments section on Facebook.
In 1952, 26-year-old Hugh Hefner left his job as a copywriter to launch Playboy Magazine—with the first issue featuring a nude Marilyn Monroe. Following Monroe's scandalous and successful debut, a number of other famous females of the time, including Bettie Page and Jayne Mansfield, helped propel the sexual revolution of the 20th century.
During the 1960s and 1970s, Playboy hit its stride—not only as the most popular men's magazine on the news stands, but as a cultural landmark. It was among one of the most progressive companies of it's time, pushing from racial diversity in private clubs during the heat of segregation and profiling controversial political figures such as George Lincoln Rockwell. However, it's fair to say that the magazine's greatest scandals belonged to the OG Playboy himself.
Throughout his lifetime, it has been said that the Hefner slept with over a thousand women—many of whom happened to be centerfolds in his magazine. Hefner was married to his first wife, Mildred Williams, from 1949 through 1959—however, following their divorce Hefner was not married again for another 40 years. In this time, Hefner had many opportunities to sleep his way around the Playboy Mansion, until saying 'I Do' to 1989's Playmate of the Year Kimberly Conrad. And in true Hefner fashion, the pair only lasted until separating in 1998, leaving the Playboy publisher a single man entering the new millennium.
Throughout the early to mid 2000s, American audiences gained a fresh perspective into the personal life of Hefner through the publicity that followed his relationships. During this time, Hefner dated numerous younger women and admitted to dating approximately seven women at a time. Some of the most noteworthy Playmates who Hefner called girlfriends included Holly Madison, Bridget Marquardt and Kendra Wilkinson—who became well-known in the world of reality television through E! Network's The Girls Next Door. However, by 2008 all three of Hefner's girlfriends decided to leave the mansion, with his main squeeze Madison ending their nearly seven-year relationship.
From 2009 through the end of his life in 2017, Hefner dated and was eventually married to Playmate Crystal Harris, who was 60 years his junior. Harris was the third and final woman to marry the Playboy publisher, who was just 31 when her spouse passed away at the ripe age of 91. And while Hefner did leave Harris and his legacy behind, the ladies man was careful to dispose of some of his best kept secret before his passing.
Although Hefner was a collector, both of memorabilia and sex partners, he feared that some of his dirtiest secrets would be dug up after his death. Which is why, Hefner decided to dispose of a casket that was filled with over 40 years of sex tapes, X-rated photos and intimate letters from celebrities into the Pacific ocean.
It's said that the most lewd items in Hefner's collection were a series of orgies that were filmed on 8mm during the 1970s. There were many famous male actors who were believed to have been in these films, who would have faced career-altering scandals if the footage was released.
During the 1990s, after the sex tape of Pamela Anderson and Tommy Lee was leaked to the world, Hefner became increasingly paranoid about his prized possessions. This led him to make the decision to dispose of his stash, leaving his security team with the responsibility of ensuring that his scandalous memories would never surface again. It's believed that Joe Piastro, the head of security at the Playboy Mansion, was responsible for disposing of Hefner's goods, at some point chucking a specially-made casket into the Pacific ocean before the Playboy publisher's death.
Maybe, several years or decades down the line, Hefner's belongs will wash up on shore or be discovered by scuba divers—however, until then, the contents of that casket will remain a mystery.