Miguel de Icaza
Miguel de Icaza founded the GNOME project, then created the Mono project, an open source implementation of Microsoft's .Net framework that drew its fair share of criticism from Linux users. That earned him his "Bad Boy" status. But Miguel wasn't content to be any-old bad boy! The man went on to leave the Linux world completely, and publicly switch over the Apple products...slamming Linux along the way.
"Even during all of my dogfooding and Linux advocacy days, whenever I had to recommend a computer to a single new user, I recommended a Mac. And whenever I gave away computer gifts to friends and family, it was always a Mac. Linux just never managed to cross the desktop chasm."