Well, it was an odd situation. The DM is an old friend (30+ years), but as a DM he's predatory and adversarial. His stated reason for allowing a party of evil monsters was because his regular group always ended up going Evil and complained about the constraints the game world put on them. He told me, "I'm doing this to show them just how pathetic they are." (To me, that's a red flag when a DM shows that little respect for his players.)
He likes to mess with the PCs, and he allowed my character to be the exception simply because he was designed to mess with them as well. While he complains about the lack of planning and teamwork, when he sees those traits coming into play his "adversarial" side comes out and he obstructs and disrupts. Any plan his players make that he's aware of *will* run into a situation specifically designed to foul the plan. And as far as he's concerned, it's cheating if they try to make plans without him being present to hear the details.
He's still my friend, but I don't play in his games any more.