24. Eric Gagne - two years, $18 million, 2005
Eric Gagne's incredible run of form from 2002-2004 earned him a two-year, $18 million contract heading into the 2005 season. Had he done that from 2020-2022, he'd have Edwin Diaz's record deal right now. It would've been a disaster, too, because those were Gagne's final two years in LA, during which he appeared in just 16 games. He underwent Tommy John surgery, followed by another procedure the following year after his comeback was halted due to complications with his surgically-repaired elbow.
23. Nomar Garciaparra - two years, $18.5 million, 2006
After the Dodgers took a one-year flyer on Nomar Garciaparra and he delivered an All-Star campaign in 2006, he was rewarded wtih a two-year, $18.5 million contract. But injuries once again took hold, and Garciaparra played in just 176 total games between 2007 and 2008. He retired following the 2009 season after 65 games with the Oakland Athletics.
22. Howie Kendrick - two years, $20 million, 2016
A World Series hero back in 2019 (at the expense of the Dodgers in the NLDS that year), Howie Kendrick was a solid but unspectacular Dodger after coming over from the LA Angels. The two-year, $20 million deal he signed didn't really pay dividends because his promising 2015 season was cut short due to injuries and then his 2016 season was beyond overwhelming (and coincided with a switch from second base to the outfield). Can't say Dodgers fans will ever forgive him for that or the go-ahead grand slam he hit in Game 5 of the 2019 NLDS to lift the Nationals over LA.