3 Red Sox contracts we were happy to see end, and 2 we’re still eager to see expire

Spending money isn’t always the cure for a championship drought. The Boston Red Sox weren’t shy about paying free agents throughout the lengthy absence of a World Series title. After they finally secured it in 2004, the club found itself handing out a lot of bad deals.

No MLB team is free of its share of bad free agent contracts and extensions. Whether through poor scouting, unforeseen injuries, or just plain old bad investments, these Red Sox contracts were killers on the books.

When these three Red Sox contracts expired, Boston cheered. The same will happen when these other two we’re eager to see expire finally come to an end.

1) Red Sox contract we were happy to see end: Pablo Sandoval

It was on November 25, 2014, when the Red Sox invited Pablo Sandoval to Boston days before the Thanksgiving holiday. A somewhat unorthodox star with the San Francisco Giants with three rings and a 2012 World Series MVP on his resume, it appeared to be a wise enough buy.

The problem is the Red Sox overextended themselves. Sandoval had two consecutive mammoth World Series performances. Having that much success in such a short period of time would have been an addition to the Red Sox roster the team couldn’t pass on.

Sandoval signed on the dotted line for five years and $95 million. As good as he was at times for the Giants, there was an obvious limit to Sandoval’s game. He could hit well but he was far from an elite player.

Sandoval put together a mediocre 2015 campaign that included a .245/.292/.366 slash line. He appeared in 126 games for the Red Sox in what would turn out to be his most successful season in Boston.

The next season included only 3 games for Sandoval after already losing the starting third base job to Travis Shaw. He was hampered by injuries throughout the season. The writing was on the wall.

The Panda would play in only 32 games for Boston in 2017. The performance was worse than his first season. The Red Sox made the decision to release him in July. He’d return to the Giants and bounce around for the remainder of his career all the while getting paid for five seasons while appearing in only 161 games for the Red Sox. 

2) Red Sox contract we were happy to see end: Hanley Ramirez

November 25, 2014, had more than the Sandoval contract. The Red Sox also inked free agent infielder Hanley Ramirez. Once a prized prospect of theirs, he first left the organization in 2005 when he was sent to the Florida Marlins in the Josh Beckett trade. It would take a few years before things came full circle. The reunion was one the Red Sox still probably wish they skipped.

Ramirez’s deal was worth $88 million over four years with a vesting option for a fifth season. It’s laughable in retrospect.

The Red Sox were buying one of the games’ more exciting but aging players. Ramirez wasn’t the .300+ hitter with 30 stolen bases per year he was early on. The 2015 campaign would be his age 31 season. It showed in the performance.

Ramirez hit .249/.291/.426 in his first season while appearing in 105 games. It was on-par with what Sanodval did, only a little more acceptable because he did rip 19 home runs and drive in 53. The 2016 season looked much better with Ramirez powering 30 home runs and driving in 111 while putting up a .286/.361/.505 slash line. This would, unfortunately, be the last of his best days in Boston. His bat continued to decline.

Perhaps one of the most questionable aspects of the Ramirez deal was how the Red Sox used him defensively. Year one had him playing in left field. His final seasons were at first base. What made him such a talent was that he was able to hit at a high level as a shortstop. He never did play good defense there or anywhere else the Red Sox tried to place him.

It all came to an end when the team released him in May of 2018. He wouldn’t get through his fourth year with the team. The vesting option was all fluff.

3) Red Sox contract we were happy to see end: Carl Crawford

Before there was Sandoval and Ramirez eating up payroll, the Red Sox had Carl Crawford. A longtime rival as a member of the Tampa Bay Rays, Crawford looked like an entirely different player when he got to Boston. His last season with the Rays included a .307/.356/.495 slash line with 47 stolen bases, 90 RBI, and more mouth-watering numbers. How could they resist signing him away from the Rays?

Crawford received a ridiculous seven-year deal from the Red Sox for $142 million. Spoiler alert: he would not play for seven more seasons on any roster.

In his two years with the Red Sox, Crawford would appear in only 161 games. Ironically matching the number of games Sandoval played for Boston, it was a precursor for future bad Red Sox contracts.

Crawford hit .260/.292/.419 in what equated to a full season. He played in only 31 during the 2012 season before a blockbuster of a deal helped Boston fans escape this deal. On August 25, 2012, the Red Sox sent him, Josh Beckett, Adrian Gonzalez, and Nick Punto with some cash to the Los Angeles Dodgers in a massive salary dump deal. It turned out to be the smartest thing the Red Sox could do. They won the World Series the very next year.

1) Red Sox contract we cannot wait to see end: Chris Sale

In the present day, it’s the Chris Sale contract that hurts the most. The good news is he has already helped the team capture the 2017 World Series. The horrific news is he has barely seen the field after 2019.

Sale was acquired in a trade with the Chicago White Sox back in 2016 in a deal that hasn’t hurt the Red Sox all that much. Despite costing Yoan Moncada and Michael Kopech, it’s hard to declare Chicago anything but the loser in the deal.

Sale was not a free agent signing. On March 23, 2019, the Red Sox signed him to an extension. For five years and $145 million, the big lefty ace would stay in town.

It did not take long for the Red Sox to have some regrets. Sale’s 2019 season was pretty bad. At 6-1 with a 4.40 ERA, he was nowhere near the Cy Young contender he had been in every year since 2012.

Unfortunately, things went from bad to worse. Sale underwent Tommy John Surgery which cost him the entire shortened 2020 campaign. He made 9 starts in 2021 and another 2 in 2022. When on the mound, Sale has been effective. It’s also only a small sample size of 11 starts these past three years. 

The contract we’re eagerly awaiting the end of concludes after the 2024 season. Will Sale find redemption before then? At least we’ll always have 2017.