3 Worst Contracts in Red Sox History

Adam Taylor McKillop
The three worst contracts in Boston Red Sox team history, including Chris Sale following his latest injury update.
The three worst contracts in Boston Red Sox team history, including Chris Sale following his latest injury update. / ASSOCIATED PRESS

Chris Sale may be the unluckiest baseball player on the planet. The baseball world was shocked when news reported the seven-time All-Star suffered a broken wrist in an apparent bike accident, ending his 2022 campaign.

It's a year (or few years) Sale will want to turn the page on as fast as humanly possible. A brief recap shows Sale missed the entire 2020 season with Tommy John surgery, returning for nine starts at the end of the 2021 campaign. This ignited the Red Sox faithful in excitement for a full year of their ace, something that hadn't seen since 2019.

Sale's disastrous 2022 then kicked off with a broken rib cage he suffered working out during the MLB lockout. He finally returned in mid-July before a freak line drive fractured the pinky on his throwing hand. That happened just 0.2 innings into his second start of the year.

Sale's year is officially done. It's another year washed away on his 2019 contract extension, bringing him officially into the conversation for the worst contracts in Red Sox team history. This should all be put into the context of his current contract, a deal he signed back in 2019 worth five years and $145 million.

Worst Contracts Red Sox History

3. Chris Sale

Sale signed his massive five-year, $145 million deal back in 2019 with the hopes of bringing the Red Sox years of success at the top of their rotation. Enter the injuries. The Tommy John surgery would have been one thing had Sale returned to his top form. It's been downhill from there. Seriously. Sale has pitched only 48.1 innings since this contract. That's $3.01 million per inning pitched. Sale has an opportunity to erase his name from this list if he comes back with vengeance in 2023, but that remains to be seen.

2. Carl Crawford

Carl Crawford may forever hold a spot on this list because of the immense expectations that came with his signing. After a glorious nine-year run, that included four All-Star appearances and a Gold Glove for the Tampa Bay Rays, Crawford inked a seven-year, $142 million deal with Boston in 2011. After two short years, the Red Sox dumped his contract. Crawford played just 161 games in Boston, including the 2011 year in which he slashed just .255/.289/.405. Keep in mind, he came over to the Red Sox with a career slash line of .296/.337/.444. Fortunately, the Los Angeles Dodgers agreed to pay most of Crawford's remaining salary. Had they not, he'd likely be No. 1 on this list.

1. Pablo Sandoval

At the end of the 2014 season, Pablo Sandoval was an important slugger in the San Francisco Giants' early 2010's dynasty. He helped them win three World Series in five years, earning a pair of All-Star appearances along the way. Boston signed the slugging corner infielder to a five-year, $95 million deal and he completely fell apart. Sandoval spent only 2.5 short years before the Red Sox outright released him in 2017, putting together a dismal .237/.286/.360 slash line and 14 home runs in 161 games. Boston then paid Sandoval $36 million the following two years while he re-joined the San Francisco Giants.

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Adam Taylor McKillop is not a FanDuel employee. In addition to providing DFS gameplay advice, Adam Taylor also participates in DFS contests on FanDuel using his personal account, username atmckillop. While the strategies and player selections recommended in his articles are his personal views, he may deploy different strategies and player selections when entering contests with his personal account. The views expressed in their articles are the author's alone and do not necessarily reflect the views of FanDuel.