Is Pablo Sandoval's Red Sox contract the worst of all-time?

Big League Stew

The inevitable divorce between Pablo Sandoval and the Boston Red Sox is almost here.  Sandoval was designated for assignment Friday and all that’s left is for the third baseman to clear waivers or for the Red Sox trade him or release him. Then — and this is the part that hurts — the team will keep paying Sandoval the $49 million he’s still owed on his five-year, $95 million contract.

What a stinker that was, huh?

Sandoval, 30, hasn’t come close to delivering on the value of the deal he signed after one of the best spans of his career. The Red Sox signed him after the 2014 postseason, in which the San Francisco Giants won the World Series and Sandoval hit .429 in the seven games against the Kansas City Royals.

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The Sandoval the Red Sox received was inconsistent at best, horrible at worst. He missed all but three games of 2016 with injury. When he was playing, he hit .237/.286/.360 with 14 homers and 59 RBIs in 161 games spread over three seasons. Even this season, when he reported to spring training in much better shape, it didn’t really help.

There’s no other way to say it — Sandoval was a disaster.

Pablo Sandoval will be paid $95 million by the Red Sox. (AP)
Pablo Sandoval will be paid $95 million by the Red Sox. (AP)

The question is, how much of a disaster? Baseball’s guaranteed contract structure has made for some bad contracts over the years. But only as the contracts have gotten richer and richer in the past decade have we seen teams paying close to $100 million in some cases for players that aren’t even at replacement level.

Sandoval will end his Red Sox days as a -2.0 Wins Above Replacement player, according to Baseball Reference. In layman’s terms, that means the Red Sox could have used a replacement-level player (a minor-league free agent, for example) and won two more games than they did with Sandoval. They also could have saved $95 million.

So we set out to quantify some of these bad baseball contracts and see if Sandoval’s is actually the worst. We’ll start with this list, which features some famously bad contracts. We distilled them down to how much the team in question actually paid the player and what his WAR was for that team, then used those to figure how much the teams paid per WAR.

(Yahoo Sports)
(Yahoo Sports)

You can see the Giants paid Barry Zito $42 million per WAR, which is like paying penthouse prices to sleep on the floor in someone’s hotel room. Even Carl Crawford, Josh Hamilton and Matt Cain produced more than Zito.

You’ll notice that Sandoval isn’t on that list. That’s because he’s on a different list. The list of players whose contracts were so bad that math can’t even quantify them properly. They’re the system breakers. The Zito/Crawford/Hamilton list is bad, but this list is a horror movie of baseball contracts.

(Yahoo Sports)
(Yahoo Sports)

The main problem with the guys on this list: They have negative WAR or, like in the case of Olivera, never played in the big leagues for the Dodgers (yet they’re still paying him). This list highlights a few awful contracts, but really, when you look at it, two really jump out: Sandoval and Ryan Howard.

Those two are the worst contracts — the biggest wastes of money in baseball history at this point. We say “at this point” because we have zero confidence that teams will learn from these mistakes. They will almost certainly throw away millions of dollars in the future.

Ryan Howard got $125 million from the Phillies for less than nothing. (AP)
Ryan Howard got $125 million from the Phillies for less than nothing. (AP)

But in a Sandoval vs. Howard matchup for worst contract of all time, it still has to be Howard. He’s been considered the worst contract in history for a few years now and, while Sandoval is a challenger for the throne, he’s not quite there.

Howard is the pick for a few reasons:

• He was paid more by the Phillies.

• His negative WAR was even more negative.

• The Phillies gave the extension to Howard two years early without any competition from the 29 other teams. Though his existing contract went through the end of the 2011 season, the Phillies showed no patience in signing Howard to the deal in April of 2010.

• And finally — and this might be a point to applaud the Red Sox — the Phillies just let Howard play out his contract, even when he was hitting .196 last season. So not only was he breaking the bank, he was draining the on-field product too. At least the Red Sox had enough sense to cut its losses and say an early goodbye to Sandoval.

So, no, Boston, Pablo Sandoval’s isn’t the worst baseball contract of all time by our math.

But being No. 2 on the list isn’t much to brag about either.

** Yahoo Sports’ Zach Pereles contributed to this report

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Mike Oz is the editor of Big League Stew on Yahoo Sports. Have a tip? Email him at or follow him on Twitter!

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