>My nomination goes to the new exectuive running Metra, Chicago's commuter rail system. Alex Clifford was introduced to everyone the day before the blizzard hit. So, here he comes to us from Los Angeles and the next day, he had to watch entire lines of his system shut down (Here and here). Not his fault. But it happened the day after he vowed to make passenger satisfaction ("a customer-centric operation") one of his top goals.
Welcome to Chicago, Mr. Clifford.
I'm sure there are a lot of people who were a lot more unlucky than Clifford. But you, dear reader, will have to supply them.