Legacy
They published the essays by Arthur C. Clarke that later formed his "Profiles of the Future". They published stories by Ray Bradbury and Ian Fleming. They interviewed Norman Mailer and Barbra Streisand.
I cannot, however, envisage Playboy returning to its past glories no matter who is in control of it.
Not so much because of the amount of porn on the Internet, but because its niche - something that is at once tasteful and yet does accept titillation as one of its purposes - has been rendered hard to comprehend, at least in the United States, as a consequence of the rise of feminism. In other cultures, Playboy's desperate fight to be taken seriously because male sexuality has never been delegitimized in those cultures as much as in the United States.
The "kind of man that reads Playboy", according to the advertisements for advertisers, might indeed have read it in 1963 - but since even reading Playboy is a furtive pleasure in today's climate, the less tasteful stuff drives it out much as crack cocaine drove out the powder that some claimed wasn't even addicting when they're both illegal.
Given that certain retail outlets in the U.S. have levelled the playing field by banning Maxim from their shelves along with Playboy, going after Esquire's turf won't work either.
Byte had its day, and Wired is filling its niche quite well; that's probably how far Playboy would have to be reinvented to be relevant, to be about something entirely different from beautiful women - as different as computers.
Maybe Harry Pearson could use a source of new investment capital? Music Lover: Entertainment for Golden Ears? After all, expensive hi-fi equipment was part of the Playboy lifestyle... and Playboy has an annual Sex and Music issue, so they acknowledge music satisfies a significant drive as well.