27 biggest free agent contracts in Los Angeles Dodgers history

It's time for a history lesson, Los Angeles Dodgers fans! A trip down memory lane of the organization's largest free agent expenditures!

The Dodgers, as of this moment, bring in the most revenue of any MLB team at $595 million and are just behind the Yankees with a $4.075 billion net worth. They've been the league's most aggressive spender over the last decade, up until Steve Cohen's purchase of the New York Mets.

That hasn't stopped the Dodgers from spending big and maintaining a high payroll, but they did take a bit of a break this offseason, as they seemingly gear up to lure Shohei Ohtani to Chavez Ravine after the 2023 campaign.

He might top this list next year, but for now, here are the 27 biggest free agent contracts in the history of the Dodgers.

27. Kirk Gibson - three years, $4.5 million, 1988

This isn't "officially" No. 29, but we couldn't exclude this deal, which propelled the Dodgers to a World Series victory in 1988. The $4.5 million (over three years!) lured Gibson, who was one of the league's best players, away from the Detroit Tigers. Nowadays, $4.5 million gets you a mid-tier reliever in the midst of a Tommy John recovery.

26. Jeff Kent - two years, $17 million, 2004

One of the best second basemen of all time, Jeff Kent signed with the Dodgers prior to the 2005 season after two years in Houston. This deal added more intensity to the rivalry with the Giants, though, because he played the previous six years before that in San Francisco. Kent spent his final four MLB seasons in LA before calling it a carer.

25. Clayton Kershaw - one year, $17 million, 2021-22

Woah, didn't think we'd be fast-forwarding this far this early on, but Clayton Kershaw's 2022 contract was on the lighter side because the left-hander was unsure of his playing future and was coming off another injury-shortened season where he logged a 3.55 ERA, the second-worst mark of his career aside from his rookie campaign in 2008 (4.26). Get used to Kershaw, though, because he'll be on this list a few more times.

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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.

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.

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.

11. Scott Kazmir - three years, $48 million, 2015

A trio of "what" here. Scott Kazmir for three years and $48 million after the 2015 season? The left-hander was admittedly rediscovering his form a bit, but his 2014 All-Star season came in the spacious Oakland Coliseum, and his post-trade deadline showing in Houston in 2015 was pretty bad. He ended up pitching 26 games for the Dodgers in 2016, didn't take the mound again until 2021 because of injuries, and was done after five games with the Giants that year.

10. Brandon McCarthy - four years, $48 million, 2014

Again ... what?! McCarthy, for the first time in years, logged a fully healthy season and was impressive in his 14 starts with the Yankees following the 2014 trade deadline. Good for him! But $12 million per year across FOUR years heading into his age-31 season knowing the injury history? Maybe Andrew Friedman's worst signing? McCarthy pitched in 155.2 innings with the Dodgers from 2015-2017 before LA traded him to the Braves. He retied after 2018.

9. Rich Hill - three years, $48 million, 2016

Dick Mountain was another Friedman signing after he came over from Oakland and logged a 1.83 ERA and 0.79 WHIP in six post-deadline starts in 2016. Then, from 2017-2019, Hill couldn't stay healthy, pitching in 63 games. Not bad, but not $16 million worth of pitching annually. Well, if you factor in his postseason appearances (2.70 ERA in 12 games totaling 50 innings with the Dodgers), that probably justified it all. He's still hanging around, too. The soon-to-be 43-year-old will be enjoying Pittsburgh in 2023.

8. Chris Taylor - four years, $60 million, 2021

It might be a tad regrettable now, but the Dodgers had to pay Chris Taylor after his All-Star 2021 campaign and dominant postseason that year. He battled injuries in 2022, but should be back on track in 2023 to serve as the super utility option the Dodgers have deployed him as for years. Hopefully, he can get back on track and fill the void after so many key players departed the last few offseasons.

7. Justin Turner - four years, $64 million, 2016

One of them was Justin Turner, who signed with the Boston Red Sox not too long ago. But after the 2016 season, JT hit free agency and the Dodgers weren't letting him go anywhere. Though all four years he signed on for featured shortened seasons due to injury, Turner was among the best third basemen in the game, dominated in the postseason, and helped the Dodgers in the 2020 World Series. We'll miss him.

6. AJ Pollock - five years, $60 million, 2019

The Dodgers bet on potential here and (kind of) got their money's worth. Pollock was solid in his debut 2019 season with LA, but only played in 86 games due to injury. He roared back in 2020 with a dominant showing and then raked in 2021, despite appearing in just 117 games. But the Dodgers traded him before the 2022 season for Craig Kimbrel, in what ended up being a bad deal for both sides. Nonetheless, Pollock finished with an .856 OPS and 124 OPS+ in 258 games with the Dodgers, who only ended up paying $32.4 million for that production. OK, not bad.

5. Kenley Jansen - five years, $80 million, 2017

At the time, Jansen signed the second-largest contract ever for a closer, and it was well deserved. The converted catcher was arguably the most dominant closer in the sport from 2012-2016. He was underappreciated because of his sometimes erratic showings, but he's still one of the best of all time and certainly the best in Dodgers history (350 saves, 1,022 strikeouts). His contract was up after the 2021 season and he signed with the Braves, where he led MLB in saves with 41. He signed a two-year deal with the Red Sox ahead of the 2023 campaign and joins far too many former Dodgers we can't stomach to mention.

4. Trevor Bauer - three years, $103 million, 2021

The self-proclaimed inventor of short-term, high AAV deals, Trevor Bauer parlayed his fraudulent 2020 Cy Young campaign into a $100 million contract, and for some reason Friedman and the Dodgers took the bait. Bauer pitched in 17 games before sexual assault allegations derailed his MLB career. The Dodgers will pay him $22.5 million to not pitch for them in 2023.

3. Kevin Brown - seven years, $105 million, 1998

Major League Baseball's first $100 million contract. WOW! Brown came over from his lone year with the Padres (he finished third in the Cy Young voting) and landed a seven-year deal, but only lasted five in LA (he was lated traded to the Yankees). Brown, from his age-34-38 seasons with the Dodgers, went 58-32 with a 2.83 ERA, 3.16 FIP and 1.10 WHIP in 137 games (129 starts). He missed a good chunk of time in 2001-2002 with injuries, but racked up over 20 WAR in his five years. Worth it.

2. Zack Greinke - six years, $147 million, 2012

Greinke never finished this contract because he opted out, but how exciting was LA when he was atop the rotation with Kershaw? The Dodgers made the right call signing him away from the Angels (who tried to keep him after acquiring him at the 2012 trade deadline) and Greinke rewarded LA with a 51-15 record, 2.30 ERA, 2.97 FIP and 1.03 WHIP in 92 starts. He was also very good in the postseason, despite the team falling short from 2013-2015. The Dodgers do this again every time.

1. Freddie Freeman - six years, $162 million, 2022

The Dodgers are known for spending like maniacs, but Freddie Freeman's $162 million contract remains the largest free agent deal in franchise history. He was lured from the Atlanta Braves after the 2021 season and led the Dodgers to an historic 111-win campaign in 2022. Unfortunately, that team fell short in the NLDS against the Padres, but Freeman led the NL in hits (199), doubles (47) and OBP (.407) in his first season with the Dodgers. We've got five more years of arguably the best first baseman of his generation. He's not slowing down anytime soon, either. This could end up being the best FA contract, in addition to the largest.

But we can't leave these non-free-agent deals out ...

Mookie Betts - 12 years, $365 million - Largest contract in franchise history, but was signed right after the famous 2020 trade.

Clayton Kershaw - seven years, $215 million - At the time, this was the largest contract ever signed by a pitcher. Kershaw was set to hit free agency after the 2014 season, but the Dodgers got this done before the campaign even started.

Matt Kemp - eight years, $160 million - Another record-breaking extension (the largest in NL history), the Dodgers signed Kemp after the 2011 season (he finished second in the MVP voting and brought home Gold Glove and Silver Slugger awards). He lasted just three years before he was shipped off to the Padres.

Clayton Kershaw - three years, $93 million - On the brink of hitting free agency after the 2018 season, the Dodgers wasted no time giving Kershaw another lucrative extension. He's a Dodger for Life.

Andre Ethier - five years, $85 million - n the middle of the 2012 season, Ethier landed this contract, but it ended up being a bad one. His 2013 and 2015 campaigns were good, but 2014 was bad and he played in just 38 games combined in 2016 and 2017. Still a very good Dodger, though.

Chad Billingsley - three years, $35 million - In the spring of 2011, the Dodgers secured their "ace." The deal was deserved, but it didn't really pan out. Billingsley took the mound just 27 times total across his final two seasons in LA, didn't pitch in 2014, and then retired after seven starts with the Phillies in 2015.