I've done many dumb things in BG, I think the worst lately is knee-jerk leveling up Eudora on turn 2, which completely throws off being able to use the digs for the next several turns without wasting lots of gold.
Patches is my new favorite hero:
Obviously got really lucky with my rolls on that particular time, but I've done a similar build with him and gotten some 1sts and a few times when it didn't work out. But I don't think I've finished worse than 5th with Patches. With any other hero that I try to do a Pirate build with I seem to end up always finishing near the bottom.