The Cub's problem is cultural. They have been losing so long that it has became part of their fiber. Even when they field good teams, they find a way to screw themselves (Bartman anyone?). They expect failure. That's something that isnt as simple as firing everyone or getting new ownership, it lies with the fans. No matter how bad the team is, Wrigley is still filled with idiots drinking Old Style. Women looking around aimlessly wearing pink cubs hats. The fans do not hold the Cubs responsible for winning, so now it has became their culture.
On another note, my grandfather watched or listened to every Cubs game for like 50 years. He was a Cardinals fan. He said the next best thing to watching the Cards win, is watching the Cubs lose.
Pujols will not be a Cub, mark it down. He is very astute when it comes to the history of the game. He realizes what the rivalry is and also knows the statistical fact that the Cubs organization is where great players go to die. These are facts.
