By all accounts, Playboy founder (and literal playboy) Hugh Hefner was very good at selling sex to the general public. Perhaps too good. That's the conclusion of the Chicago Tribune editorial board in an assessment of his declining Playboy empire. They trace the company's "long fall" to an "an excess of sex-cess": Hefner succeeded so much at "push[ing] sex into the open" that the skin trade "has given way to a free-for-all, with the emphasis on 'free.'"

The editorial is tied to business headlines about Hefner's announcement that he wants to take Playboy Enterprises Inc. private. Observers aren't sure why he wants to do this—the company continues to hemorrhage money—but the Tribune seems to support the move. The editors explain that the business "Hefner pioneered went so mass market -- supply as well as demand -- that much of it is now free on the Internet."

Even before the Internet changed the economics of the media world, Playboy operated more like a private company than a public one. Hef's heavy stockholdings let him control it, and the high expenses of running his California mansion and supporting his cherished magazine made little business sense. For years, his daughter Christie served as chief executive, and only after the stock price dwindled to almost nothing at the end of 2008 did she step aside, to be replaced by an outsider. Making money typically took a back seat to Hef's priorities: changing popular attitudes toward sex and keeping the party going. ...

Hef has said that he instead wants to pass on the company to his youthful sons, Marston and Cooper. His latest offer may be the original playboy's last chance to secure a future for a younger generation of playboys still in the making.