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17. Ted Lilly - three years, $33 million, 2010
After acquiring Ted Lilly at the 2010 trade deadline, the Dodgers rewarded the veteran lefty with a three-year deal thanks to his 3.52 ERA, 0.99 WHIP and 77 strikeouts in 12 starts that summer. But only one of those seasons under the new contract panned out. Lilly made just 13 starts across 2012 and 2013 due to injury. In this day and age, his first 45 starts with the Dodgers might've been worth $33 million, though.
16. Hiroki Kuroda - three years, $35 million, 2007
A couple international signings on this slide, too! Hiroki Kuroda left Japan following the 2007 season to sign a three year, $35.3 million contract with the Dodgers. He spent the previous 11 years with the Hiroshima Carp before moving stateside. In all, he spent four years with the Dodgers and finished 41-46 with a 3.45 ERA, 3.55 FIP, 1.19 WHIP and 523 strikeouts in 115 games. Not bad at all.
15. Derek Lowe - four years, $36 million, 2005
After helping break the curse in Boston and logging a postseason for the ages en route to the Red Sox' 2004 World Series victory, Derek Lowe signed a four-year, $36 million contract with the Dodgers. It ended up panning out for both sides. The right-hander spent all four seasons in LA, compiling a 54-48 record with a 3.59 ERA, 3.77 FIP and 1.23 WHIP in 137 games. He averaged well over 200 innings per season over that span and led the NL in wins in 2006.
14. Hyun-Jin Ryu - six years, $36 million, 2012
This time dipping into the Korean market, the Dodgers landed left-handed stud Hyun-Jin Ryu after an impressive seven-year run with the Hanwha Eagles in KBO. Though he didn't pitch for 2.5 out of the six years due to shoulder surgery/complications, Ryu finished fourth in the Rookie of the Year voting in 2013 and then won the ERA title and was named an All-Star in 2019 (finished second in the Cy Young voting). Then he departed for the Blue Jays and underwent Tommy John surgery in 2022. With the Dodgers, he went 54-33 with a 2.98 ERA, 3.32 FIP and 1.16 WHIP in 126 games.