27 biggest free agent contracts in Los Angeles Dodgers history
21. Clayton Kershaw - one year, $20 million, 2022-23
Kersh again! This contract is from this offseason, after he decided to play at least one more year and have it be with the only team he's ever known. Following yet another injury-shortened season (but one that featured a 2.28 ERA, sub-1.00 WHIP and an All-Star Game appearance), the left-hander got a bit of a raise and hopes to make his age-35 campaign a memorable one.
20. Joe Kelly - three years, $25 million, 2018-19
Don't you miss this guy? He loves Dodgers fans and he still hates the Houston Astros, even though they didn't do anything to him! Though Joe Kelly helped the Red Sox defeat the Dodgers in the 2018 World Series, he signed with LA the very next year but struggled mightily as his shoulder began to fatigue (and required surgery after the 2020 season). Though this largely ended up being a sunk cost, he had a very good showing in 2021 and gave Dodgers fans a moment they'll never forget when he buzzed Carlos Correa and cleared the benches in Houston for taunting the Astros.
19. Kenta Maeda - eight years, $25 million, 2016
Right before the 2016 season, the Dodgers went out on the international market and swiped Kenta Maeda from Japan on a pretty insane eight-year deal that had a whole lot of incentives attached to it due to concerns with the right-hander's elbow. In the end, he was fully healthy during his four years with the Dodgers (3.87 ERA and 1.15 WHIP in 137 games) before being traded to the Twins in the Brusdar Graterol deal. He finished second in the Cy Young voting during the shortened 2020 season with Minnesota, but then finally required the feared Tommy John surgery in 2021 (he missed all of 2022 as a result).
18. Brad Penny - three years, $25.5 million, 2005
After coming over in the Paul Lo Duca trade with the Marlins, Brad Penny was rock solid in 2005, which earned him a three-year deal with the Dodgers. He was an All-Star in 2006 and 2007 before the wheels came off in 2008, and he was never the same after that. He led the NL in wins in 2006 and finished third in the Cy Young voting in 2007, though. We'd say that's worth what he got.