In order to garner attention for his brand-new publication, a men’s lifestyle magazine he titled Playboy, Hugh Hefner took the audacious step of featuring actress Marilyn Monroe in the nude for the debut issue in December 1953. Monroe didn’t pose for the magazine, though: Hefner bought her nude images from a previous modeling session that took place in 1949, before Monroe’s career had taken off. Hefner paid $500 for the photos. He sold out his print run of 70,000 copies. The rest is history.

Following Hefner’s death in September 2017 at age 91, some of his personal effects have made their way to the auction block. The latest collection, which will be featured in a Julien’s Auctions sale running November 30 and December 1, includes Hefner’s personal copy of that first issue, which is expected to fetch between $3000 and $5000. The original cover price was 50 cents.

Courtesy of Julien's Auctions

Also on tap at the auction: a custom-made Playboy Monopoly board game (which is estimated to sell for between $6000 and $8000); a leather Los Angeles Lakers jacket with the Playboy insignia (worth $3000 to $5000); an Underwood Standard portable typewriter Hefner used in college (valued at $300 to $500); his trademark smoking jacket (which should go for $3000 to $5000); and Hefner’s entire personal collection of Playboy, all bound in leather volumes, which experts value somewhere between $20,000 and $40,000. Proceeds from the auction will be directed to the Hugh M. Hefner Foundation, which supports civil liberties and First Amendment rights.

While Hefner’s copy of that first issue is expected to generate considerable interest, it continues to provoke considerable controversy, as using Monroe’s photos was deemed exploitative. She did appear, at least publicly, to have a sense of humor about inadvertently launching Hefner’s empire. “Her famous comment was, ‘I had nothing on but the radio,’” Hefner told NPR in 1999. “And that classic reaction in that very repressive time—because one must remember ... how really conservative the '50s were—for a major star to ... treat it in such a casual way with humor was a revelation, and a very welcome one.”

If you’re in the Los Angeles area, you’ll be able to browse the collection in person from November 26 through November 30.