Despite a bankruptcy filing by home builder WCI Communities, its chairman may just have a reason to smile.

Carl Icahn has to be glad he did not end up buying all of WCI Communities last year.

In March 2007, after talks with the company did not go anywhere, the activist investor launched a tender offer for all WCI shares at $22 each, but the company’s board at the time rejected it. The billionaire investor instead ended up as chairman of the company after a protracted proxy battle.

Turns out, that was the better outcome for Icahn, although it wasn’t his finest hour in demonstrating a Midas touch for shareholders.

WCI has now filed for Chapter 11 bankruptcy protection after failing to obtain financing to stay afloat. Icahn said in a statement, “The company, with all diligence, has attempted to avoid a bankruptcy filing. However, the filing became necessary.”

The luxury builder, whose business is concentrated in Florida, one of the states hardest-hit by the housing downturn, sought bankruptcy protection after failing to meet an Aug. 5 deadline for restructuring $125 million in convertible bonds.

Its shares plunged 48 percent to 66 cents a share.

Of course, the company’s bankruptcy has cost Icahn, who this past week had better luck with some of his other holdings like ImClone (although he is so far turning his nose up at Bristol-Myers’ offer to buy the chunk of the biotech company it doesn’t already own). He still owns about 15 percent of WCI, or about 6 million shares. But it sure beats owning the entire thing.

(Photo credit: Reuters)