I am honestly not sure that Cuddy was ever all that assertive, and I definitely see he trailing after House even in Season 1. It took her forever to get rid of the new Chairman of the Board even though he was clearly bad for the hospital from day one. Now, the money would be a reason not to kick his ass to the curb the first day, of course. But, she didn't really stand up for anyone, including House, during the whole thing. He ended up rescuing her.