Everybody loves the underdog -- until it comes out on top
The Santa Cruz Operation
Once upon a time -- the time being the late '70s, and the place being Santa Cruz, a groovy college town on the southern fringe of Silicon Valley -- a group of hackers (in the original sense of the term) banded together to create what Eric Raymond called the "first Unix company" -- which is to say the first Unix vendor that wasn't a hardware manufacturer or a telephone company. As you might expect from that time and place and industry, the atmosphere was a bit relaxed; employees soaked in the company hot tub and, according to some uncited info on Wikipedia, would walk the halls of the office naked. Over the course of the '80s and '90s, the company -- now going by the somewhat more corporate-sounding abbreviation "SCO" -- maintained its good reputation among Unix users, and acquired some rights (exactly which ones would later prove controversial) to AT&T's System V Unix.
Then, in the early '00s, SCO pivoted, and made an ultimately failed all-in bet on a product called Tarantella that allowed users to access applications remotely via a browser-based Java applet. In 2001, SCO changed its name to Tarantella, and sold all of its Unix rights -- and the SCO brand -- to a Linux company called Caldera Systems, which promptly redubbed itself with the SCO moniker it had just purchased.
Tarantella crashed in the early-'00s dot-com bust, and its remains were scooped up by Sun in 2005. By that time, the the leadership of the new SCO had dragged the old company's name through the mud: in 2002, the company claimed that IBM had stolen System V code and put it into Linux, which meant that every Linux user was infringing on SCO's property. SCO quickly became a byword for bullying in the Linux and open source community. After the better part of a decade of legal wrangling, US courts finally decided that not only did IBM not infringe on System V copyrights, but SCO never actually acquired the rights to those copyrights from Novell in the first place; by that time, though, any goodwill one might have had towards the long-dead Santa Cruz Operation was at least a little tainted by the actions of the ex-Caldera. Branding is all in business, after all.
Picture courtesy of Flickr user CanadaGood