YNOT – Perpetual playboy Hugh Hefner is locked in a new kind of high-stakes game, the outcome of which could determine the fate of the 84-year-old Playboy magnate’s 57-year-old iconic brand.On Monday, Hef said he has lined up enough backing to buy all outstanding shares of Playboy Enterprises Inc. and take the company private in a deal valued at $185 million.

Within hours, FriendFinder Inc. Chief Executive Officer Marc Bell said his company intends to make a formal bid for Hef’s financially troubled empire, which has not been able to find its footing in the digital era. FriendFinder is the parent company of longtime archrival men’s magazine Penthouse, a harder-edged version of ultra-softcore Playboy.

FriendFinder’s flagship and most profitable product is a network of dating websites — exactly the kind of operation to which Playboy has been losing market share since the dawn of the internet age. According to Publishers Information Bureau, venerable Playboy magazine, Playboy’s flagship product, has seen advertising sales slide from 765 pages in 2000 to less than half that — 311 pages — in 2009. Over the same period, the magazine’s circulation plunged by about a million copies, to 2.02 million last year.

Paid circulation and advertising revenues once formed the foundation of Playboy’s revenue, but now the company derives the majority of its income from licensing its brand to consumer-product manufacturers of underwear, lingerie, watches, drinks and slot machines. Licensing revenues generated a net income of $21 million in 2009, compared to only $1.6 million from the magazine and the associated website. Broadcast revenues added another $9.9 million to the company’s bottom line.

By teaming with private equity firm Rizvi Traverse Management LLC, Hef was able to corral $122.5 million for the outstanding shares of Playboy stock. The proposed $5.50 per share represented a 40-percent premium above Friday’s closing market value of $3.94 per share. The offer itself generated a flurry of trading, and by Monday afternoon Playboy’s per-share price had climbed to $5.54.

Hefner, Playboy’s titular creative director, owns more than 4 million of the 33.6 million shares of stock the company had issued by the end of April.

Playboy’s board of director told the Associated Press it had received no formal offers by Monday afternoon. A committee established especially for that purpose will consider any formal offers, a board spokesperson said.