Like i've said in other threads, Ilitch is fucking loaded, he has his hands in the Tigers, Red Wings, every arena in Detroit, amusement parks, etc. Little Caesars is his, all of the LC's distributors are his, all of the primary vendors, etc so he basically just moves his own money around and banks it all. There is no reason for the Tigers to ever be cheap ever.
Of course this contract will end badly. Derp. BUT, here is the rub. If you want these HOF players to spend all of their prime HOF years on your team, you have to be willing to pay them for the decline years. That's the trade off. Otherwise, he walks in two years while he's still a triple crown threat, and the same people laughing at the overpay are instead laughing because they lost the superstar.
Look around. Pujols. Votto. Cabrera. When these mega stars have deals come up from 28-31, it's a tough spot to be in for the franchise. They know the deals will end badly. What you hope for is that their bodies stay in one piece and the decline is gradual and not sharp. You can live with a 38 year old Cabrera or Votto OPS'ing .820 if they give you 1.000 for 5-6 years of the deal. What you can't live with is a complete falling off the shelf after year one or two, which Pujols is in danger of doing because of his lower body failing him.