The Los Angeles Dodgers, under Andrew Friedman, have become known for making prudent decisions in free agency and only flexing their financial muscle when they're confident they're making a choice that will work in both the short- and long-term.
There are, of course, a few exceptions where Friedman tripped over his own feet and slammed teeth-first into a steel grate. Those'll make this list.
For the most part, though, the Dodgers' history in free agency is only gruesome until Friedman takes the reins. For many years, they shied away from the market after being stung a few times in the early years of the process, only rededicating themselves after swiping Kirk Gibson worked so spectacularly.
On the flip side, Ned Colletti wanted anyone and everyone on three- and four-year pacts. Some hit. Most didn't. They're here.
HONORABLE MENTION: Kevin Brown's 7-Year, $105 Million Contract (1998). Objectively, Brown's massive deal -- which changed baseball -- worked out fairly well for LA. He was quite brilliant in his first three years, bad in Year 4, and excellent again in Year 5. By Year 6, he was a Yankee. Four out of seven "thumbs up" years makes this contract a default win, but ... it's certainly the original long-term cautionary tale. If dominating for 57% of the contract is good, then maybe people should be more cautious before signing deals like these.
15 Worst Signings in Los Angeles Dodgers History
15. Juan Pierre: Five Years, $44 Million, 2006
The problem with giving Juan Pierre $44 million and five years of security is that ... he's always been Juan Pierre. The Dodgers got exactly what they paid for: a below-average offensive player camouflaged as a good one because his skills were flashy and he "threw it back" to a bygone era when men were men and bunts were bunts.
Pierre was a fun guy to have on your team, but not once you paid him. He posted OPS+ marks of 77 and 75 in his first two years in Dodger Blue before hitting .308 with a 105 OPS+ (!) in his final season, 2009, before he was dealt to the White Sox.
In Chicago, he turned on the jets, stealing a league-leading 68 bases. In LA? 64, 40, and 30.
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