5 worst contracts in Boston Red Sox history

There are a lot of parallels between the Yankees and the Boston Red Sox. Fierce rivals in the AL East, they are also rivals when it comes to free agency. Their willingness to spend and desire to add championships matches that of their counterparts.

Naturally, both teams are forces to be reckoned with when it comes to free agency. They have the financial resources to plug any holes on their roster, capable of taking on salary whenever needed. This has allowed the Red Sox to be a contender more often than not in recent years.

The five worst contracts in Boston Red Sox history

This has also led to some utter disasters in free agency. That push to win has led to some horrendous contracts, either due to injury or because those players were a terrible fit. While every team has those contracts they wish they could take back, those deals get far more notoriety in places such as New York or Boston.

The Boston Red Sox have plenty of contracts they wish they could take back in franchise history. Let’s take a look at the five worst deals.

5. Daisuke Matsuzaka

The Boston Red Sox and New York Yankees both coveted Daisuke Matsuzaka when he entered the posting system.

It was easy to see why. He was the top pitcher in Japan, someone who was considered to be a guaranteed ace when he came stateside. The Red Sox won his services with a six year, $52 million deal, with a $51.1 million posting fee. While Matsuzaka drove the fanbase mad with his penchant for nibbling at the corners, he was solid in the first two years of the deal.

Then it all fell apart. He was beset by a seemingly never ending list of injuries over the final four years of that deal, including Tommy John surgery. He made just 56 appearances over those four years, posting a 5.53 ERA and a 1.537 WHiP in his 296 innings. The promise from the beginning of his time in the majors was over.

Matsuzaka did manage to stick around the majors for two more years after his time with the Red Sox was over. He made seven starts for the Mets in 2013 before converting to the bullpen in his final season in New York. Once that contract was over, he headed back to Japan where his injury woes continued to hound him. Matsuzaka finally retired this past year, making one final appearance in 2021 before hanging up his cleats.

Although Daisuke Matsuzaka did not work out for the Boston Red Sox, it was not a total loss. After all, his heading to Boston led the Yankees to sign Kei Igawa.