Ranking the five worst value MLB contracts of all-time

Jacoby Ellsbury
It's not a surprise to see Jacoby Ellsbury among the worst MLB contracts. Photo from NYT.

With each passing year, the contracts given to MLB free agents seem to get higher and higher. Of course, not all of those contracts work out with the recipients quickly turning into the most overpaid MLB players.

Worst MLB contracts of all-time

Over the years, there have been some truly terrible contracts given out that didn’t work out for the teams at all. Let’s take a look at some of the worst baseball contracts of all time.

Jacoby Ellsbury –  7 Years, $153 million

The Yankees thought they were pulling a fast one by stealing one of Boston’s biggest stars from their biggest rivals.

But Jacoby Ellsbury was a disaster from the start.

For four years, he was solid but unspectacular, never producing an OPS better than .750 and not coming close to earning his salary. Then came the injuries that kept Ellsbury from playing in 2018 or 2019 before the Yankees finally just released him, paying nearly half of the $153 million for years in which Ellsbury never stepped foot on the field.

Pablo Sandoval –  5 Years, $95 million

Pablo Sandoval was already showing some signs of decline when the Red Sox handed him a big contract. He was a considerable disappointment in 2015 and only played three games in 2016 due to injury.

Midway through the 2017 season, the Red Sox were fed up and just released him midway through the five-year deal. Sandoval returned to the Giants where he started his career and eventually turned things around, becoming a solid part-time player.


Prince Fielder –  9 Years, $214 million

Prince Fielder made a name for himself with the Brewers and then signed his huge deal with the Tigers, the team where his father was a star for many years.

He had two good years in Detroit before being traded to the Rangers.

That’s when everything started to fall apart. While he helped Texas reach the postseason in 2015, the injuries began in 2016 and eventually forced Fielder to end his career early. He ended up playing just five years of the nine-year contract, leaving the Rangers on the hook for a lot of money.

Carl Crawford –  7 Years, $142 million

Carl Crawford excelled with the Rays for many years but was an immediate disappointment after the Red Sox gave him a $142 million contract.

His numbers were down in 2011 and a wrist injury limited his impact in 2012. After it was clear that Boston and Crawford were a bad fit, the Red Sox traded him to the Dodgers. He ended up having a couple of decent seasons in Los Angeles but was never the star his contract said he was. Eventually, the Dodgers released him with a year and a half left on the seven-year deal.

Rusney Castillo – 7 years, $72.5 million

This often gets overlooked as one of the worst MLB contracts ever.

Even before he made his debut in the majors, the Red Sox promised Rusney Castillo, who defected from Cuba, a seven-year, $72.5 million deal.

But he never came close to living up to the contract.

Castillo ended up only playing 99 games in the majors, hitting a modest .262 with seven home runs. He was eventually designated for assignment but cleared waivers and spent three full seasons playing in triple-A but being paid a big league salary.

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About Bryan Zarpentine 220 Articles
Bryan Zarpentine is a freelance writer and editor with most of his work focusing on the world of sports. He is a 2008 graduate of Syracuse University and still resides in upstate New York.

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