Nothing harder then trying to figure out when you need to go over your bosses head and when to lay back and see what happens.

I would suspect that the Cann situation didn't develop until this past off season. Henderson, in his role as pitching coach, might have not been exposed to as much of it as other coaches either. He also may not have wanted to rat Cann out, hoping he would right the ship once the season started. It's a tough call. I've been there with a boss before.