Every offseason general managers everywhere forget how many free agents turn into busts. The short-sighted memory has led to some unsightly deals that can cripple a team for years to come. For every C.C. Sabathia or Cliff Lee deal, there’s a Chone Figgins, Alfonso Soriano, or Aaron Rowand mistake.
Here are the five worst deals still current in baseball, beginning with the fifth most-crippling deal:
5. Daisuke Matsuzaka: Boston, 6 years $103 million—Matsuzka’s $103 million includes the mammoth $51 million fee the Red Sox paid his former Japanese team. Even if that number isn’t included in the total, his last three seasons are still a bust—with another one still remaining.
Dice-K’s second season (18-3, 2.90 ERA) in 2008 was far and away his best in Boston. Had he continued that he would have been worth the price of his deal—though still not a bargain. Even then, the fluke season contained an ominous sign as he still led the league with 94 walks in just 167 innings.
The last three injury-riddled seasons have produced a 16-15 record with a combined ERA of 5.03 in just 40 starts.
Why it’s here: The $103 million commitment has yielded one good season out of five with one to go. With just one good season under his belt, it beats out dishonorable mention contracts given to Aaron Rowand, Chone Figgins, and even Alfonso Soriano—but just barely. Soriano’s deal still has some scary amounts left to be paid, but he’s at least shown some power in his time at Wrigley.
4. John Lackey: Boston, 5 years $82.5 million—After eight seasons as the Angels’ workhorse starter, Lackey went to Boston following the 2009 season and struggled a bit in 2010 with a 4.40 ERA in his 33 starts.
