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.
4. Edgar Renteria
You know that a contract was a disaster when a player comes to be called Rent A Wreck. Such was the case with Edgar Renteria during his time with the Boston Red Sox.
The Red Sox thought they had their long term answer at the position when Orlando Cabrera left in free agency. Renteria had been an All Star in 2003 and 2004, a two time Gold Glove winner with a solid all around game. As he was just 28 for the first year of that four year, $40 million deal, it seemed as though the Red Sox had even gotten a bargain.
It turned out that Rentaria just could not handle the pressure in Boston. He lasted only one season with the Red Sox before being shipped, along with a considerable amount of cash, to Atlanta for Andy Marte. Renteria produced a disappointing .276/.335/.385 batting line in his 692 plate appearances, hitting eight homers and 36 doubles. While that was not terrible, his 30 errors, costing the Red Sox 30 runs at short, were.
He just needed a change of scenery to return to form. Renteria was an All Star again in 2006, his production back to expectations. He had another strong season in 2007 before his bat began to fade, although he had enough left in the tank to win the World Series MVP in 2010.
The Boston Red Sox thought they had their long term answer at short in Edgar Renteria. That long term answer lasted for just one year.
3. Rusney Castillo
The Boston Red Sox hoped that Rusney Castillo would be another Yasiel Puig or Yoenis Cespedes. He was not even close.
He was reportedly rusty as he had not played baseball in nearly two years when he made his major league debut. Castillo showed some promise in that brief stint in the majors in 2014, notching 12 hits, including two homers, in his 40 plate appearances. He was listed as the 21st best prospect in the game by Baseball America heading into the 2015 season as the sky appeared to be the limit.
Instead, those ten games were the highlight of his Red Sox tenure. He was mediocre in 2015, posting a 72 OPS+ in 289 plate appearances, and then received just eight more plate appearances during his time in the organization. While he was solid in Triple-A, the Red Sox outrighted him from the 40 man roster and never brought him back, making his six year, $72.5 million contract even more of a disaster.
The Red Sox were finally able to move on from Castillo after the 2020 season. He signed in Japan for 2021, appearing in a grand total of 50 games with three extra base hits. His time in the Mexican Winter League was better, but none of his 17 hits went for extra bases.
The Boston Red Sox hoped that they would have a star for their outfield in Rusney Castillo. Instead, they essentially lit $72.5 million on fire.
2. Pablo Sandoval
It is sad that the most memorable moment of Pablo Sandoval‘s tenure with the Boston Red Sox is more memorable for a comedic moment than any production he would have had.
That moment came when Sandoval’s belt broke during a plate appearance. He had already received a great deal of derision for his lack of conditioning, although round is a shape. While he was able to appear in 126 largely forgettable games in 2015, that was the highlight of his time in Boston.
Injuries left Sandoval to appear in 35 more games with the Red Sox before he was released. Sandoval ended up returning to the Giants where he turned his career around and once again became a useful part of the lineup.
That was not the case at all with the Red Sox. His signing had seemed questionable at the time, a way to sell panda heads to casual fans, and his performance did nothing to dispel that thought. He produced a .237/.286/.360 batting line in 620 plate appearances, hitting 14 homers and 27 doubles. In exchange for a five year deal worth $95 million, the Red Sox received approximately a year’s worth of playing time.
Pablo Sandoval was a questionable fit with the Boston Red Sox from the beginning. Yet somehow, his was not the worst contract the team had handed out.
1. Carl Crawford
It seemed that whenever the Rays faced off against the Boston Red Sox, Carl Crawford was doing his best to make their lives miserable.
Naturally, when he became a free agent at the end of the 2010 season, the Red Sox opened the vaults to bring him in. He signed a seven year deal worth $142 million to head to Boston, theoretically adding a dynamic element to the lineup that the team had not had in years.
Instead, Crawford was not the same. He had a slow start to his time in Boston, and then battled injuries. While he attempted to come back in 2012, he clearly was not ready. In the end, the Red Sox unloaded him to the Dodgers as part of a salary dump, with Josh Beckett, Adrian Gonzalez, Nick Punto, and a good amount of cash. It did not matter what the Red Sox got back; they were just happy to see him elsewhere.
The Red Sox clearly did not get their money’s worth. Crawford produced a disappointing .260/.292/.419 batting line in 664 plate appearances, hitting 14 homers and 39 doubles while stealing 23 bases. While he was marginally better with the Dodgers, injuries continued to take their toll and prematurely ended his career.
Next. A reason for Ortiz not receiving Shaughnessy's vote. dark
The Boston Red Sox could not figure out how to get Carl Crawford out when he was on the Rays. Turns out that they just needed to sign him to keep him off the bases.