5 worst contracts in modern Los Angeles Dodgers history

When the Los Angeles Dodgers spend big bucks, they typically know what they’re doing.

That’s what makes their expensive failures so glaring — and so out of character they can almost be a little bit funny.

What are the top pitfalls of free agency, after all? Splurging on a contract you don’t need just to spite a rival. Paying for someone’s prime four years or more after the fact. Giving three years of security to someone who deserves just one. Paying Andrew Heaney.

Alright, fine, we’ll wait until after the season to drop him onto the list.

For now, it’s safe to say the Dodgers front office hasn’t failed nearly as often as their haters would like them to. The fallacy of a bloated budget is that you can’t “buy a championship,” and more often than not, big-budget mega-deals are massive overreaches from the front office, desperate swings to paper over an underdone roster.

Not in LA, though. Andrew Friedman doesn’t “spend huge” to build a mega-team. He uses his massive well of available finances to maintain core players and make prudent additions/absorb big contracts at the trade deadline. In reality, the worst deal the modern Dodgers have ever made wasn’t about contracts they signed, but about inexplicably absorbing some one else’s (Josh Beckett? Carl Crawford?).

On our list, these “worst contracts” will never include a massive expenditure that could go sour in later years, but delivered a title in the here and now. Could the Mookie Betts deal turn into an albatross by Year 7? Sure, but we’re not going to apologize or make excuses for it. Sorry the best player in baseball took a downturn by age-37 after already leading you to a title (with more possibly to come)!

No, our “worst contracts” are the straight-up head-scratchers of the bunch that never paid off, as well as a few character concerns who shouldn’t have been rewarded with the money they received by any team, let alone the Los Angeles Dodgers.

Apologies to Darren Dreifort; definitely a gaffe, but doesn’t feel like a part of the same era of Dodger baseball we’re discussing. He’s free to be a pre-modern mistake, and merits only an honorable mention here.

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The 5 worst contracts in Los Angeles Dodgers history

5. Scott Kazmir

We’re not sure what the Dodgers liked in Scott Kazmir’s profile during the 2015-16 offseason, but this is certainly the expenditure that can be most clearly criticized as “paying for payment’s sake.”

At the time, Kazmir was coming off a tale of two halves in 2015. An All-Star for the Oakland A’s in 2014, the left-hander posted a 5-5 record with a 2.38 ERA in 18 starts before being traded to the Astros for the first stretch run of the Altuve/Springer/Correa era for two ancillary pieces. There, he bottomed out, going 2-6 with a 4.17 ERA and striking out just 54 in 73.1 innings pitched.

That’s what led the Dodgers to extend the olive branch to him to the tune of three years and $48 million, which used to be the team’s free agent cap on pitcher contracts in the post-Dreifort/Kevin Brown Era. We’ll get to that later.

Kazmir only pitched one of those three seasons for the Dodgers, a 2016 campaign in which he went 10-6 with a 4.56 ERA. Due to various compounding injury concerns, he wouldn’t make another major-league appearance until four starts in 2021 with the Giants (!), which makes it fair to call this deal a bigger swing-and-a-miss than any Kazmir ever induced with his changeup in Dodger Blue.

Even without the final injury blow, this was a questionable commitment at best.

4. Jason Schmidt

And Luis Gonzalez, and Mike Lieberthal … the whole press conference, really.

Just look at Jason Schmidt up on that podium. After starring as a San Francisco Giant for five and a half seasons, the Dodgers were extremely ready to pay for his age-34 campaign and the two more that followed, offering the burly change-of-speeds right-hander a three-year, $47 million deal that he accepted with aplomb.

Only one problem: Schmidt forgot to tell the Dodgers he was cooked.

Coming off his final All-Star season in San Fran (11-9, 3.59 ERA in 213.1 innings), Schmidt was all smiles on the day of his introduction, but rarely brought that joy to the mound in the ensuing three years.

In fact, he rarely brought anything to the mound, making just 10 starts combined, all coming in 2007 and 2009, when he rounded out his career with a 5.60 ERA in 17.2 innings pitched. Here’s the kicker: we’d like to say you can’t fault the Dodgers for a deal that ended with a catastrophic injury, but … they knew Schmidt had a severe rotator cuff problem, and they didn’t care!

Now that’s how you end up on a “worst contracts” list, no matter the decade. Add in the Giants keeping the upper hand here, and it’s official.

3. Hector Olivera

As much as we might want to pin the Hector Olivera decision on the Atlanta Braves, where the memory of his disaster has lingered longer, it was the Dodgers who were the ones to win the bidding here, creating one of the largest overpays in the modern game for someone who absolutely did not deserve a fraction of the cash.

Sound familiar?

Los Angeles signed the Cuban defector prior to the 2015 season, adding him on a six-year, $62.5 million deal with a $28 million signing bonus. A precautionary MRI revealed he had a minor UCL tear, so the Dodgers insured against an eventual possible Tommy John surgery; other than that, though, the team believed they’d added a developing power threat in the wake of Yoenis Cespedes’ successful defection.

Just four months later, Olivera was gone, traded to Atlanta in a three-team deal that brought LA a massive bounty including Mat Latos, Michael Morse, Bronson Arroyo, Alex Wood, and several others.

The very next April, Olivera was arrested in Washington, DC over a domestic dispute; he was sentenced to a 90-day prison term and became one of baseball’s highest-profile domestic violence offenders, suspended for 82 games and ultimately jettisoned to San Diego in a salary dump for Matt Kemp, where he was later DFA’d. The Cuban import never played Major League Baseball ever again.

The Dodgers may not have paid off the bulk of this deal, but the responsibility still lies in their court.

2. Andruw Jones

Oh, you mean the contract keeping Andruw Jones out of the Hall of Fame? Of course! That one!

Just two years ago, we would’ve told you this Jones deal was the undefeated National Champion. How could anything top it? Well … sometimes, life gets in the way.

It’s worth dwelling on this contract, though, because it really doesn’t feel like an exaggeration to say the bloated end of Jones’ spectacular career is keeping him out of Cooperstown despite a truly special peak both in the field and at the plate, and the narrative started to shift when he joined the Dodgers — with little to no warning.

Jones’ two-year contract was worth $36.2 million, signed prior to the 2008 season when the center field superstar was just 31 years old. He was coming off his worst career campaign, sure (26 bombs, 94 RBI, .222 average, and just an 87 OPS+), but he was also just one season removed from 41 bombs, 129 RBI and elite defense.

Also, come on! He was 31! 31!! One of the best athletes and power bats in the modern game! Two years and $36.2 million wasn’t just a reasonable bounce back contract. It seemed like one of the clearest steals in the game.

Anyway, Jones showed up out of shape, hit .158 in 75 games with three homers and 14 RBI, and found himself on the Texas Rangers roster by the time the second year of his contract came around, released by the Dodgers at a massive loss in January 2009. It’d be hilarious if it weren’t so cruel.

Eventually, Jones found his power bat again and became a serviceable bench bat who could swing for the fences with the 2010 White Sox and 2011 Yankees (120 and 126 OPS+ marks, respectively) before ending his career on another sour note the with the ’12 Yanks.

That wasn’t Jones, though. Jones wasn’t supposed to be remembered as a paunchy bat who couldn’t run or throw. And the significant dings to his historic reputation began with the worst possible theoretical season in Los Angeles.