The legendary Cuban Cohiba cigar, manufactured by state-owned Cubatabaco, is said to be the favorite brand of one of the world’s most notorious cigar aficionados, Fidel Castro. But after more than a decade of litigation over the Cohiba trademark, if Castro (or anyone else) buys a Cohiba in the United States, it will be a General Cigar product. On Wednesday–only eight days after oral arguments in an expedited appeal–the U.S. Court of Appeals for the Second Circuit overturned an injunction barring General Cigar from using the Cohiba name, which it first registered as a trademark in 1992.

This remarkable case, which dates back to Cubatabaco’s 1997 challenge to General Cigar’s mark at the Trademark Trial and Appeal board, has a history as tangled as Castro’s beard. In 2000 Cubatabaco, represented by Michael Krinsky of Rabinowitz, Boudin, Standard, Krinsky & Lieberman, filed a trademark infringement case against General Cigar in Manhattan federal district court (thereby staying the trademark board challenge). After a 2004 bench trial, Manhattan federal district court judge Robert Sweet dismissed the Cuban company’s New York state unfair competition claims but enjoined General Cigar from selling its Cohibas on federal trademark infringement grounds.

The Second Circuit heard the case for the first time in 2005, when General Cigar’s then-appellate counsel from Latham & Watkins (working with the company’s trial counsel from Morgan & Finnegan) raised the question of whether the injunction could stand under U.S. laws barring the import of Cuban goods. After soliciting–and disagreeing with–the views of the U.S. government, the Second Circuit overturned the injunction against General Cigar in 2006.

But Cubatabaco wasn’t ready to give up, even when the U.S. Supreme Court denied its petition for certiorari (after asking the Solicitor General to opine on the issues of international law and diplomatic relations the case raised). In 2008 Rabinowitz Boudin’s Krinksy returned to Judge Sweet, asking him to reverse his dismissal of Cubatabaco’s New York state unfair competition claims in light of a 2007 ruling in an unrelated case.

Over the objections of General Tobacco’s new lawyers from DLA Piper, Judge Sweet took the extraordinary step of reinstating Cubatabaco’s New York state claims and granting the Cuban company judgment on them. Four years after first ordering an injunction, and two years after it was reversed on appeal, Sweet again enjoined General Cigar from using the Cohiba name.

“It was almost unprecedented,” said General Cigar counsel Andrew Deutsch of DLA. “We’d never seen anything like this.”

With the injunction stayed, General Cigar turned once more to the Second Circuit for help. (It took Judge Sweet until January 2010 to enter judgment for Cubatabaco and order the injunction.) Early in July, Deutsch and Krinsky presented arguments to Second Circuit judges Reena Raggi, Gerard Lynch, and Denny Chin. Eight days later, in a per curiam ruling, the panel found that the 2007 case Cubatabaco cited to Judge Sweet did not offer sufficient grounds for reopening its case.

Krinsky told us that Cubatabaco is disappointed in the ruling and considering its options–which include continuing to prosecute its 14-year-old case at the trademark board.

Deutsch said his client is going to continue selling its super premium Cohibas, which, despite two injunctions, have been on the market continuously since 1992.

To our disappointment, both Krinsky and Deutsch report that they’re not cigar smokers, so we presume they haven’t personally tested the merits of one Cohiba against the other. Krinsky told us a funny story, though. A fellow who hangs around outside of his downtown Manhattan office has a habit of sidling up to people and whispering surreptitiously that he has Cohibas for sale. “I know two things,” Krinsky said. “One is that whatever he’s selling, it’s not Cohibas. The other is that I’m not going to smoke them, whatever they are.”

This story originally appeared in The Am Law Litigation Daily, a Corporate Counsel sibling publication.