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.