Looking only at active contracts, Tim Dierkes of MLB Trade Rumors came up with a list of the 45 worst.
There are several teams with 3 contracts listed, and that's how many the Yanks have:
It's too easy to say Jorge's deal is a bad one. He was the best catcher on the market when the Yanks needed a catcher. The Mets were prepared to open the vault and the Yanks had no other options. On any other team Jorge would be the franchise player and the clean-up hitter; you overpay those guys and hope for the best.
In a way, the Matsui pick is the one I agree with most. It's not as hard to find a left fielder as a catcher, so I can't justify the move with the Jorge logic. But when he was signed he had never missed a game, and $13M was reasonable to good even at the time for a player capable of .280/.390/.500. Guys get hurt, the money isn't obscene (see Giambi, Jason), and we don't have a clear picture of how much money Hideki brings in from Japan (tickets+sales). Hard to call the deal an albatross.
Obviously there's no point arguing over Kei Igawa from a monetary standpoint, but the Yanks have the most money and never have a decent draft pick, so they have to get creative. If the move hadn't looked like such an overreaction to the Bo-Sox getting Dice-K I suspect most people would look at it the way I do: the scout who recommended El Duque recommended Igawa, and it didn't work. But whether it's signing Jon Lieber for a year of rehab and a year of work, or it means importing talent, it's the only way the Yanks can restock.
Sure, some of these guys have underperformed (or Igawa-ed, as we call it in the jscape household), but none of these deals have the air of franchise changing a la Barry Zito. Is it just me, or does it seem like Dierkes felt that with Giambi and Pavano gone, some Yankee still had to make the list?