I guess the construction of this list could be pursued from a number of different angles:
1) The worst current contracts.
2) The worst contracts in MLB history, which would subsume angle 1 above..
3) The contracts that were assessed as bad even as they were being announced, (i.e., there was a general assessment that the player simply was not worth it at the time of signing).
4) The contracts that were assessed as bad after the fact (i.e., the player did not live up to expectations for whatever reason (e.g., injury, loss of motivation, eating chicken and drinking beer)).
In the first case, Carl Crawford certainly has to rank up there, although guys like Alfonso Soriano might contend. Even John Lackey gets an honorable mention here. Perhaps Zito, too. Hmm, Vernon Wells? Jason Werth?
In the second case Jason Giambi might be right up there. Mike Rocky-Mountain-High Hampton could easily fill this bill.
In the third case, Danny Tartabull might quench the thirst here. Oh, oh, close to home we might inject Julio Lugo.
In the fourth case, you gotta mention Bobby Bonilla somewhere. Richie Sexson might compete. Even Mo Vaughn might fill the space. And an honorable mention might go to Todd Hundley (I knew his dad so it hurts me to suggest him here)
And after it's all said and done, where in god's name do we put Daisuke Matsuzaka? Other names that might fall into this "Where in the World is Carmen San Diego" category are: Carl Pavano, Kevin Brown, Matt Davis, Milton Bradley.
Of course, all of these are post-free agency era contracts, which might suggest it might be worth considering a sub-strata of candidates within the 4 categories above for pre- and post-free agency. I haven't taken it that far. Would Babe Ruth fit in here?
Edited by SoxJox, 14 February 2013 - 06:10 PM.