Actually, if you look at the guild's history on their website, they've been around longer than wow. They have their roots in playing Ultima Online, and were part of the wow beta. Apparently blizzard added the syndicate in-game faction as an homage to the guild, not the other way around. So yeah, completely legit.

@ evets25

Is that actually true? With actual references or a quote where someone says that, I mean, because as mentioned above that is a quite generic name - if I had created a group and called it "The Syndicate" I would never have heard of the trademarked guild name before.

The website I was referring to that talks about the guild's history and their involvement in the wow beta can be found here: http://www.llts.org/History.php?p=64WoWBeta

The guild has been around for a very, very long time, and their history, which has been so painstakingly documented on their website makes for a fascinating read. If you read a bit of it you'll understand why the guild is considered famous/noteworthy enough to merit having its own trademark. Well, that or whatever the criteria is for trademarking something. They obviously satisfied the court system, and IMHO they deserve the recognition.