I think he's royally messed up in Detroit. It's amazing that they are paying 12 million a year each to 3 guys who hardly pitch for them or don't pitch at all (Nate Robertson, Dontrelle Willis, Jeremy Bonderman). Other guys like Carlos Guillen and Magglio Ordonez are also way overpaid. They also paid Sheffield this year to play for the Mets. Even Cabrera doesn't have a great contract relative to the market, although he, at least is productive.
With so many bad contracts no wonder the tam is in financial trouble and now their big move is to trade two very productive players who are very cheap for what they produce (in MLB terms). If he has a coherent plan in all this I can't see it.