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From Crawford to Panda to Sale: The worst contracts in Red Sox history

BOSTON -- Chris Sale is hurt. Again. He'll miss the rest of the 2022 after breaking his wrist from a fall off his bicycle.

That is Chris Sale in a nutshell since he signed a big five year, $145 million contract with the Red Sox in 2019. He's spent more time on the IL than on the mound for Boston, making his current contract one of the worst in Red Sox history.

Is it the worst? That is up for debate, since the Red Sox have handed out a handful of other horrendous contracts over the last 20 years. (They have four World Series in that span, so at least they have that going for them.)

Maybe guys like J.D. Drew, John Lackey and David Price should be on this list. They all got boatloads of money from Boston and, at times, didn't really live up to those paychecks with the Red Sox. However, they all played crucial roles in bringing World Series trophies to Boston, and winning is all that really matters. (Hey, it isn't our money, right?)

Sale also helped the team win a title in 2018, but that was before he was given his massive extension by Dave Dombrowski. When you see what he has done -- or rather, hasn't done -- since the deal kicked in, it's impossible to make this list without his inclusion.

But is Sale the worst? Maybe not. Not yet at least. And again, as your blood boils during this trip down memory lane, just remember this isn't our money being flushed down the drain. But here are the five worst contracts given out by the Red Sox -- in no particular order.

Carl Crawford

The contract: Seven years, $142 million

This is the worst of the worst right here. The Sox gave Crawford a lot of money to come to Boston from Tampa Bay in 2011, but he was never able to handle the spotlight of a big market. His production went down across the board, as he hit a then career-low .255 in his first season with the Sox.

That season came to an end on the final day of the regular season, as Boston capped off an epic September collapse with a late-inning collapse to the Orioles. The Red Sox held a 3-2 lead heading into the bottom of the ninth, which was gone when Nolan Reimold clubbed a ground-rule RBI double off Jonathan Papelbon. Robert Andino followed with a soft liner to left, which Crawford made a less-than-enthusiastic effort to catch. Reimold scored the winning run, and with the Rays beating the Yankees, Boston was eliminated from the postseason in the most embarrassing way possible. They were atop the AL East to start September, and held a nine-game lead over the Rays in the Wild Card race when they lost that footing, but went 7-20 to finish the season.

Terry Francona was fired and Bobby Valentine was brought in, leading to an even bigger disaster in 2012. Crawford began that season on the 60-Day DL after undergoing offseason wrist surgery and didn't debut until July. He underwent Tommy John surgery on Aug. 23, and two days later, he was dealt to the Dodgers along with Adrian Gonzalez, Josh Beckett and Nick Punto as the Red Sox reset the franchise.

Pablo Sandoval

The contract: Five years, $95 million

This one was a dooooooozy. Following a last-place finish in the division in 2014, Ben Cherington went out and tried to make some sexy signings in the offseason. He brought in Sandoval, who was a two-time All-Star and had a knack for big swings in the postseason, winning three World Series as a member of the Giants.

The man known as Kung Fu Panda put up disappointing numbers his first season with the team, hitting a career-low .245 with only 47 RBIs. The Sox once again finished in last place in the AL East.

Sandoval played only three games in 2016 before undergoing season-ending shoulder surgery. The only memorable moment of that season -- and his Red Sox career, really -- was when he murdered his belt with a massive swing-and-a-miss against the Blue Jays.

BOS@TOR: Panda's belt breaks during his at-bat by MLB on YouTube

He hit .212 over 32 games in 2017 before the Red Sox designated Sandoval for assignment. He was released by Boston with almost $48 million remaining on the books. 

Hanley Ramirez

The contract: Four years, $88 million

Ramirez was signed the same offseason as Sandoval, and at least he nearly made it to the end of the deal. It was supposed to be a feel-good story, with Ramirez returning to the team that initially signed him as an amateur free agent in 2000, but his stint in Boston was anything but.

Since he and Sandoval were both third basemen, Ramirez was moved to left field. It was not pretty. Ramirez hit just .249 with just 53 RBIs over 105 games, and when mixed with his poor defense -- which was rated the worst in the AL -- he had a -0.7 WAR for the season.

He was moved to first base in 2016 and actually played well at the new position and had a big season at the plate. Ramirez crushed 30 homers and drove in a career-best 111 runs over 147 games, helping Boston to an AL East crown. But he hit just .250 and drove in only two runs as the Red Sox were swept in the ALDS by Cleveland.

Ramirez moved to DH in 2017 following David Ortiz's retirement, but his bat went silent. He just .242 and drove in only 63 runs over 133 games. He hit a robust .571 in the postseason, but the Sox were once again swept in the ALDS, this time by the eventual World Series champion Astros.

After a hot April in 2018, Ramirez hit just .163 for the month of May. He was DFA'd on May 25 and released five days later.

Rusney Castillo

The contract: Seven years, $72.5 million

The Red Sox signed the Cuban phenom in August 2014 to a deal that ran through 2020. He debuted in Boston less than a month later. He played in 10 games for the Red Sox in 2014, hitting .333 with a pair of homers. He started 2015 in Triple A but was called up in late May and played in 80 Major League games.

That is the bulk of Castillo's Major League career. He played only 99 games for the Red Sox over three seasons, spending the rest of his career in Triple A for luxury tax purposes. No matter how well he was playing in Pawtucket -- he led the International League in batting in 2018 -- Castillo remained in Triple A because of his contract. 

Overall, Castillo spent five seasons with Pawtucket, appearing in 467 games. He may have been a PawSox legend, but that's a lot of dough for a minor leaguer.

Edgar Renteria

The contract: Four years, $40 million (plus a team option)

That's not a huge amount of money by today's standards, but it was a pretty big investment for the Red Sox. Renteria was brought in to replace Orlando Cabrera following the team's 2004 title, and was a complete disaster.

Renteria struggled out of the gate, hitting just .228 in April. He bounced back with a .354 month of May, but finished the year slashing .276/.335/.385. He hit just .231 in Boston's ALDS sweep by the Chicago White Sox.

Where he earned his "Rent-A-Wreck" nickname though was in the field. Disaster is an understatement, as Renteria committed 30 errors at short.

Theo Epstein moved on from this mistake quickly, dealing Renteria to the Atlanta Braves in December for prospect Andy Marte. In his introduction wit the Braves, Renteria blamed the field at Fenway Park for all those errors in 2005.

Chris Sale

The contract: Five years, $145 million

This all brings us back to Sale. Seemingly everyone but Dombrowski and Boston ownership knew it was a bad idea to give Sale a huge extension after he struggled to finish the 2018 season. He continued his career trend of falling off in the final months of the season, but the Sox gave him all that money anyways.

It hasn't paid off, obviously. Since Sale's extension began in 2020, he has made just 11 regular season starts and three postseason starts for Boston. His postseason ERA is at 8.00 over nine playoff innings since the extension kicked in.

It has been injury after injury after injury since the end of the 2019 season. He was on the IL with elbow inflammation in August, but it was determined that he didn't need Tommy John surgery. That changed a few months later, but not before the start of Sale's 2020 was delayed due to pneumonia. Shortly after the season was delayed because of the COVID-19 pandemic, it was announced that Sale had undergone Tommy John and would miss all of 2020. He also missed most of 2021 while he recovered.

The injury misfortune bit again in 2022. The start to his season was delayed after Sale fractured a rib while throwing before spring training. He suffered a pair of setbacks during his rehab to push his return back even further. (He also demolished a TV in Worcester after a rehab start, but managed to escape any injury from that incident.)

When he did return to the bump for Boston, it didn't last long. In the first inning of his second start of the season, Sale broke his pinkie off a comebacker. Now, he's done for the year after falling off his bike.

The Red Sox got 5.2 innings from Sale in 2022. He's made more trips to the IL than the mound. The Red Sox are paying him $30 million for the season.

Sale has an opt-out after this season, but chances of a recovering pitcher turning down $27.5 million are as slim as Sale's build. He'll also make $27.5 million in 2024, before his salary dips to $20 million in 2025.

Those three years will at least give Sale a chance to redeem himself. But if he keeps suffering odd, non-baseball injuries and spends more extended time on the IL, he'll be contending with Crawford for the worst contract in Red Sox history.

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