1. Andruw Jones: Two Years, $36.2 Million, 2007
From a pure production standpoint, it's hard to get around Jones' deal being the worst. It represents everything misguided about Ned Coletti's regime. It reflected poorly on Jones, and might be keeping him out of the Hall of Fame as an enduring image of his regression. It's an all-time stinker, even on a short-term deal.
Jones joined the Dodgers after his first below-average offensive year in Atlanta, an age-30 season where he hit 26 homers and knocked in 94 runs, but with a .222 average, .311 OBP and 87 OPS+. Even the solid power numbers look pedestrian in the context of his career; he was one year removed from drilling 41 bombs and knocking in 129 runs, and two years past launching 51 homers, piling up 128 RBI and finishing second in the MVP race.
With the Dodgers, Jones was a shell of himself, often out of shape and participating in just 72 games in a Dodgers uniform. The cliff he fell off was steep; in 2008, Jones hit .158 with a trio of homers in 72 games. His OPS was .505. His OPS+ was 35. This is a future Hall-of-Famer.
The next year, he found himself shipped to Texas ... where he rebounded somewhat to smack 17 homers in 85 games, posting a league-average 100 OPS+. The next two seasons, with the White Sox and Yankees, he was a serviceable bench slugger, posting 120 and 126 OPS+ marks, though he looked nothing like the man who once patrolled center with ease in Atlanta.
As strange as late-career Jones was, at least he produced ... everywhere but Los Angeles. Any time a Hall candidate -- and likely eventual inductee -- hits .158 with no pop for you and forgets his glove in Georgia, he has to earn the No. 1 spot.