The Original Mansion Was Supposed to be in Chicago
Hefner was born and raised in Chicago before making his way west to Los Angeles. In the late ’50’s, he purchased the mansion shown above — with the purpose of making it the official Playboy spot. It was said to cost Hefner $400,000 (which by today’s standard, would have cost roughly $8.6 million).
However, as Hefner continued to meet more and more influential people based on the West Coast, it would make more sense for him to abandon this project in favor of a mansion in Southern California. Today, the Chicago mansion is actually seven separate units.
Image Source: Raymond Boyd/Michael Ochs Archives/Getty Images