15 worst Los Angeles Dodgers free agent signings in franchise history

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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14. Luis Gonzalez: One Year, $7.5 Million, 2006

Placed firmly in the, "Wait, what the hell?" category 16 years later, the Dodgers signed former Diamondbacks World Series hero Luis Gonzalez to a relatively hefty one-year deal prior to the 2007 season. At the time, he was 39 years old and coming off a 99 OPS+ season in the desert.

The plan for Gonzalez was ... uh ... "sign former enemy, hope he continues to reverse the aging process, profit"? He wasn't particularly awful with the '07 Dodgers, but his contributions amounted to a 139-game shrug.

Gonzo posted a 104 OPS+, combined with rickety old man defense. He hit .278 with a .793 OPS in an inflated offensive environment. He was an utterly forgettable addition to an 88-win team on the precipice of turning over a number of key offensive positions to youngsters (Russell Martin, James Loney, Matt Kemp). Instead of progressing, the team won 82 games and Gonzalez finished his career with the Marlins the very next season. This was supposed to work because he was a former division rival who'd be born anew in Hollywood. He was mostly an average clog.

Anyway, thinking about the David Peralta contract for no reason at all.

13. Hector Olivera: Six Years, $62.5 million ($28 million signing bonus), 2015

The only reason the Olivera contract doesn't rank higher is because the Dodgers were able to get him excommunicated from their farm before things went truly sour.

Olivera was mostly an Atlanta Brave after signing a March 2015 deal to defect to MLB, but the Dodgers did have to pay his massive signing bonus ... and, in exchange, received six games in Double-A and seven in Triple-A before he was part of a three-team whirlwind that sent Mat Latos, Bronson Arroyo, Alex Wood, Michael Morse and others to help make over the '15 Dodgers.

Olivera, of course, racked up -0.3 WAR during his MLB career and was suspended 82 games the next season under the league's domestic violence policy. He retired at 32 after a brief stint with the independent Sugar Land Skeeters. Horrendous, by every measure.

12. Manny Ramirez: Two Years, $45 Million, 2009

At least Manny was fun in portions of the 2009 season! But MannyWood was knocked down and rezoned after 2008, when the Jason Bay-Craig Hansen-Andy LaRoche swap resulted in one of the most exciting Dodgers summers/postseasons in years.

Ramirez started his fresh, two-year contract with a bang the next season, hitting .348 through May 7 ... when it turned out the jig was up. One of the greatest hitters of his generation was hit with a 50-game PED suspension, and though he came back to do his typical damage in the postseason (.308 in the NLDS against the Cardinals, .263 with a homer against Philly), the magic was never recaptured.

Despite hitting .311 with eight bombs in 66 games the next season, Ramirez had clearly worn out his welcome once again in the city it seemed like he'd own forever two summers prior. The Dodgers traded him to the White Sox in 2010, and his MLB career ended the next season after an unsuccessful stint in Tampa.

11. Scott Kazmir: Three Years, $48 Million, 2015 (with deferred salary into 2021)

Kazmir was an odd signing all around for a Dodgers franchise that's usually fairly good at risk appraisal.

He'd already battled back from the brink once during his career; Kazmir turned his top prospect pedigree into two All-Star seasons with the Rays, but posted a 5.92 ERA in the first half of the 2009 season, a 1.73 ERA in six second-half starts after being dealt to the Angels ... and then a 5.94 mark in 28 starts with the 2010 Angels. It was over ... until Cleveland recaptured the flame in 2013, and the Oakland A's received a 15-9, 3.55 ERA All-Star campaign from Kazmir in 2014.

His first half in 2015 was also excellent, but he scuffled after being dealt to the Astros ... and it was at that point that the Dodgers decided to get on the roller coaster. Kazmir went 10-6 with a 4.56 ERA for the 2016 Dodgers, but came down with hip issues that decreased his velocity tremendously. He missed the 2017 season, was traded to the Braves prior to 2018, and never pitched for them.

The left-hander didn't resurface until 2021 with the Giants, when he was subsisting on deferred money from the Dodgers in order to pitch for their chief rival.

10. Brandon McCarthy: Four Years, $48 Million, 2014

McCarthy was another rare miss for Friedman's front office, occurring in his first offseason at the helm. Best to get 'em out of the way early.

The mercurial right-hander was coming off an extremely successful run with the New York Yankees following the 2014 trade deadline (7–5 with a 2.89 ERA in 14 starts), and Friedman got suckered into paying for past performance and ignored the injury concerns along the way.

McCarthy missed significant time with the Texas Rangers early in his career rehabbing both elbow and shoulder issues, which prevented him from becoming one of the game's top young pitchers. Ultimately, he made just four starts with the 2015 Dodgers and nine with the 2016 team, having Tommy John surgery in between on April 30, 2015.

He recovered to post a solid 92.2 innings for the 2017 Dodgers, but his only World Series appearance featured a George Springer dinger and the loss in Game 2.

9. Brett Tomko: Two Years, $8.7 Million, 2005

For some reason, the Dodgers saw Brett "Bombko" Tomko's 190.2 innings with a 4.48 ERA/only 114 Ks for the 2005 San Francisco Giants and decided, "Yeah, we need some of that."

The Dodgers poached a 33-year-old Tomko from their rivals, as they often did in those days (we'll get to it...), and received one brutal season and a midsummer DFA the next year for their troubles.

Tomko posted a 4.73 ERA in 44 outings (15 starts) in 2006, then further regressed the next year, posting a 2-11 record and 5.80 ERA in 33 games before getting the axe and winding up on the Padres for the remainder of the 2007 season.

The pinnacle of his career, from that point forward, was a 2.95 ERA in a six-start stretch for the 2009 Oakland A's. Probably not worth the trouble.

8. Don Stanhouse: Five Years, $2.1 Million, 1979

Remember those early free agent deals that scared the Dodgers off from the process altogether? If they could do it again, they probably wouldn't have hitched their wagon to aging Orioles relieverDon Stanhouse for the back end of his successful career.

There are ways to take advantage of the free agency cycle. That's not how it's done. But hey, during the '70s, people didn't know any better.

When the Dodgers signed Stanhouse, he was a 28-year-old All-Star reliever for the AL Champion O's, coming off a 2.85 ERA season in 72.2 innings (tellingly not missing any bats, though, en route to whiffing just 34).

When they actually got Stanhouse, he was a 5.04 ERA guy who pitched just 25.0 innings in LA before he was released early on during the 1981 season. Back then, when it went, it went swiftly for pitchers. Surgeries were rudimentary. Sometimes, 29-year-olds just ended up with chewed gum and tape in their AC joints, and that was the way it was.

Needless to say, Stanhouse pitched more like an outhouse.

7. Brandon League: Three Years, $22.5 Million, 2012

League ranks only seventh because an AAV of $7.5 million can be swallowed by any big-league organization, but ... the contributions over the course of this deal certainly don't justify the investment.

The hard-throwing right-hander with the wild black hair became the Dodgers' de facto closer at the end of the 2012 season after coming over from Seattle, earning himself a payday entering 2013 ... when he regressed to the norm, posting a 5.30 ERA in 58 games.

Even worse? Somehow, even with his electric fastball, League struck out just 28 men in 54.1 innings. How is that possible?

He actually bounced back to post a 2.57 ERA (3.40 FIP) in 63 innings of middle relief the next season, but came down with a shoulder issue and was eventually DFA'd without throwing a big-league pitch in 2015. One out of three ain't bad ... or, wait, sorry, actually it is bad. Pretty bad.

6. Darryl Strawberry: Five Years, $20.25 Million, 1990

Darryl Strawberry's defection from the Mets to the Dodgers after the 1990 season was a massive moment for the National League playoff picture, but it didn't turn out momentous for very long.

Coming on the heels of successfully resurrecting Kirk Gibson's career, the Dodgers became less gun shy in free agency, guaranteeing Straw five years after he hit 37 bombs with a 140 OPS+ and third-place MVP finish in '90. However, the warning signs were there. He'd hit just .225 as a 27-year-old for the '89 Mets (29 bombs, 125 OPS+), and the behavioral issues that marked his time in New York weren't going away.

Strawberry's 1991 season in Los Angeles was a success; he made another All-Star team, finished ninth in the MVP race, and replicated his 140 OPS+. Unfortunately, he played just 43 games in 1992 and 32 in 1993, hitting .237 and .140 in those seasons. His release came in 1994 after he failed to show up for a game, and he was suspended for cocaine usage in 1995.

Strawberry's road to recovery was a long one, and his addiction issues had roots in New York. However, his time with the Dodgers is often seen as the moment when his habits overcame him.

5. Darren Dreifort: Five Years, $55 Million, 2000

The gold standard for confounding pitching deals during the first free agency boom of the late '90s/early '00s, Darren Dreifort was everything Kevin Brown wasn't after the Dodgers panicked when he hit the market following the 2000 season. They could've simply let him walk. They chose ... unwisely.

Dreifort, a Dodgers bonus baby in the early '90s, missed the entire 1995 season and battled persistent arm issues during his career in LA, during which he posted a 39-45 record prior to reaching free agency. Scott Boras somehow played the Dodgers like a fiddle, assuring them that their fringe-average pitcher would be choosing the "rival" Colorado Rockies in the coming weeks. OK? You'll take that?

Somehow, that spooked the Dodgers, who paid Dreifort handsomely to post a 5.13 ERA in 16 starts in 2001 before missing the entire 2002 season to have elbow reconstruction surgery. According to doctors, he suffered from a degenerative tissue condition and a deformed femur, which threw off his mechanics and shattered his durability.

By 2004, those same doctors were warning he no longer had the capacity to be a starter. Dunno. Probably would've made a great Rockie.

3. Jason Schmidt: Three Years, $47 Million, 2006

The Brett Tomko move didn't work? Well, why not double down, Vince Vaughn-style, by signing the early-aughts Giants ace? That should hit 'em where it hurts! Well...

When the Dodgers signed Jason Schmidt, he was coming off his age-33 season, a year where he hurled 213.1 regular-season innings, made the All-Star team once again, and posted a 3.59 ERA/3.95 FIP. He wasn't spectacular, but he was steady, a good bet to age well considering all the ground balls he induced with his hard sinker.

Sadly, the Dodgers lost this bet tremendously. In three years, Schmidt made just 10 starts, posting a 6.31 ERA in 2007 and a 5.60 mark in 2009. But hey, at least we got to see his trademark soul patch in Dodger Blue for a little! Certainly a good deal for a brief period of the '06-'07 offseason in terms of "owning the Giants," but Schmidt did precious little else during his Dodgers tenure -- and that team was good! Could've really used him!

2. Trevor Bauer: Three Years, $102 Million, 2021

Not placing Bauer's monstrosity of a contract in the No. 1 spot is difficult, but ... the production was there, ever so briefly, in Year 1 of the deal back in 2021.

Bauer, coming off an empty-stadium Cy Young year where he experimented with spin rate in Spincinnati, went 8-5 with a 2.59 ERA in 107.2 innings, striking out 137 and popularizing the sword celebration. The signing didn't come without controversy the previous spring, when LA outbid the Mets at the horn to bring Bauer to California. The righty had a history of online bullying and didn't address his transgressions very satisfyingly before taking the mound in LA, instead meeting with a bullied child at spring training, a clear good deed that still seemed like a, "Hey, look over there!" at the time.

The worst was, of course, yet to come. Bauer was suspended in the summer of 2021 for 324 games (later reduced to 194) for his accused role in a sexual assault case. Further allegations followed in the initial complaint's wake, and Bauer has now found himself to be persona non grata in MLB after being released by the Dodgers this offseason.

1. Andruw Jones: Two Years, $36.2 Million, 2007

From a pure production standpoint, it's hard to get around Jones' deal being the worst. It represents everything misguided about Ned Coletti's regime. It reflected poorly on Jones, and might be keeping him out of the Hall of Fame as an enduring image of his regression. It's an all-time stinker, even on a short-term deal.

Jones joined the Dodgers after his first below-average offensive year in Atlanta, an age-30 season where he hit 26 homers and knocked in 94 runs, but with a .222 average, .311 OBP and 87 OPS+. Even the solid power numbers look pedestrian in the context of his career; he was one year removed from drilling 41 bombs and knocking in 129 runs, and two years past launching 51 homers, piling up 128 RBI and finishing second in the MVP race.

With the Dodgers, Jones was a shell of himself, often out of shape and participating in just 72 games in a Dodgers uniform. The cliff he fell off was steep; in 2008, Jones hit .158 with a trio of homers in 72 games. His OPS was .505. His OPS+ was 35. This is a future Hall-of-Famer.

The next year, he found himself shipped to Texas ... where he rebounded somewhat to smack 17 homers in 85 games, posting a league-average 100 OPS+. The next two seasons, with the White Sox and Yankees, he was a serviceable bench slugger, posting 120 and 126 OPS+ marks, though he looked nothing like the man who once patrolled center with ease in Atlanta.

As strange as late-career Jones was, at least he produced ... everywhere but Los Angeles. Any time a Hall candidate -- and likely eventual inductee -- hits .158 with no pop for you and forgets his glove in Georgia, he has to earn the No. 1 spot.

READ MORE: 27 Biggest Free Agent Contracts in Dodgers History