By: Scott RossPublished: July 12, 2022

Chris Sale: Red Sox Savior or Dumbest Contract in Team History?

Chris Sale makes his 2022 debut for the Boston Red Sox Tuesday night, taking the bump against the Tampa Bay Rays. Sale could provide a much needed boost to the Sox, whose pitching staff has been in such disarray that they recently started a rookie pitcher in four consecutive games, plus the timing couldn’t be much better as the Sox and Rays are 1-2 in the American League wild card race, with Boston nursing a half-game lead over Tampa.

In his final rehab start before joining the team, Sale went 3 and two-thirds, giving up just one run on one hit and striking out five, but he also allowed five walks and was so pleased with his performance that upon being pulled from the game, he promptly smashed a TV monitor to bits. How Sale fares tonight could also go a long way toward answering just where his 2019 contract will rank in Boston history.

As of right now, it has to be considered the dumbest.

A franchise with pockets as deep as the Boston Red Sox’ does not go 86 years between titles without making a number of boneheaded personnel moves along the way. There was the infamous trade of Babe Ruth to the Yankees, the passing over of both Jackie Robinson and Willie Mays, the 1980-81 off-season administrative debacle that cost them Carlton Fisk, the Jeff Bagwell for Larry Andersen trade... But in terms of contracts, there has never been one that has cost so much, borne so little fruit, and been so entirely unnecessary as the one given to Sale, the one-time staff ace, ahead of the 2019 season.

Following a 2016 season in which they got swept in the American League Championship Series, the Red Sox decided to reload for another title run, trading to the Chicago White Sox two of their very best prospects, fireballer Michael Kopech and stud infielder Yoan Moncada, in return for Sale, who was at the time the best pitcher in the American League, having led the league in Wins Above Replacement (WAR), ERA+ and strikeouts over the previous five seasons. Additionally, Sale was just 27, and had three years left on his contract at less than $14 million per. It was a roll of the dice, shipping out two blue-chip prospects for a win-now player, exactly the kind of trade for which General Manager Dave Dombowski is famous: mortgaging the future to win today.

Sale lived up to his billing in 2017, leading the team with 17 wins, and the league with 214.1 innings, 308 strikeouts, a 2.45 Fielding Independent Pitching (FIP), and 12.9 strikeouts per 9 innings, as the Sox defended their AL East title, before losing to the Houston Astros 3-1 in the ALCS, with Sale getting lit up for 9 runs over 9.2 innings on 13 hits, including 4 dingers, taking L’s in Games 1 and 4.

The 2018 Red Sox were one of those lightning-in-a-bottle powerhouses, a team for whom everyone played their best and every ball bounced their way as they steamrolled their way to an 108-win season. But in July, shortly after making his third straight start for the AL All-Star team, Sale went on the disabled list with shoulder inflammation. He would come back for a day to beat the Orioles, before going back on the shelf for another four weeks with the same malady. From his return on September 11 to the end of the regular season, he pitched 12 innings, striking out 18, but with an ERA of 3.75. It was an omen of things to come.

Sale was used sparingly throughout the 2018 playoffs, as he was clearly not healthy. He pitched 5 1/3 innings in an ALDS Game 1 victory over the Yankees, then came back four days later to pitch the eighth to help secure the win. He went just 4 innings in a Game 3 loss to the Astros, his only action during that 5-game series. In Game 1 of the World Series against the Dodgers, he managed to last just 4 innings, giving up three runs, but the Red Sox offense exploded for 8 runs to save the day. Five days later, Sale dragged his raggedy arm out to the hill for the ninth inning of the Game 5, striking out Justin Turner, Kiki Hernandez and Manny Machado in order to secure the game and the team’s fourth title in 15 seasons. He was a Red Sox legend, but he was also damaged goods with another year on his contract at just $15 million.

What happened next will give Red Sox fans night-sweats for decades to come. On March 23, 2019, while he was still under contract, just eight months after he originally went on the DL with shoulder inflammation and one week short of his 30th birthday, Sale watched the Sox back the money truck up to his door with a five-year extension worth $145 million. Six days later, on Opening Day, Sale took the bump in Seattle and lasted 3 innings, giving up 7 earned runs on six hits – 3 of them homers – and 2 walks to send the Sox on their way to a 12-4 loss. He would eventually somewhat steady the ship, with a 3.58 ERA over his next 20 starts, while going 5-8 and whiffing 178 over 120.2 innings -- fine numbers for a #2 or #3 starter, but not for a $29 million ace. The wheels finally came off in back-to-back home-and-away starts against New York, as the Bombers lit Sale up for 14 runs on 14 hits (4 homers) over 9 innings in the span of six days. On August 17, Sale went back on the DL with elbow inflammation for the rest of the season, though it was decided that he would not need Tommy John surgery (wait for it…). He finished 2019 with a record of 6-11, a 4.40 ERA and 218 strikeouts over 147.1 innings, having given up a career-high 1.5 home runs per 9.

In September 2019, following a 5-0 loss to the Yankees that dropped their record to 76-68, 18 and half games out of first, the Red Sox fired Dombrowski. He was subsequently replaced with Chaim Bloom, the wunderkind who for years had kept the Tampa Bay Rays competitive on a shoestring budget. The following February, the Boston Red Sox dropped a bomb: they were trading Mookie Betts, at the time the second-best player in baseball, along with starting pitcher David Price to the Dodgers, for Alex Verdugo and two prospects. The company line is that management was convinced that Betts had already decided to leave town, but this was a straight-up salary dump, as Boston avoided paying Betts $365 million over 12 years, and got out from under the last 4 years and $128 million left on Price’s contract. The same team that had needlessly promised Chris Sale $145 million couldn’t afford Mookie Betts.

Weeks later, it was announced that Sale would not be ready for Opening Day, in part because pneumonia was hampering his rehab. On March 19, the team announced—here it comes—that Sale was undergoing Tommy John surgery; he wouldn’t pitch again until August 14, 2021. He pitched reasonably well in 2021, if not “$29 million” well, going 5-1 with a 3.16 ERA in 42.2 innings over 9 starts, though his strikeout and home run rates were each moving in the wrong direction. Oh, and he missed a start in September when he tested positive for Covid. Still, there was reason to think that maybe, just maybe, Boston could get the old Chris Sale back. Until a couple of weeks ago, that is, when the team announced that Sale has a stress fracture in his rib cage and will once again not be ready for Opening Day. Right now the best-case scenario is he misses a month of the season.

To review: the Red Sox had a 30-year-old injured pitcher under contract for 2019 and signed him to a 5-year, $145 million extension. Since then, he’s gone 11-12 with a 4.12 ERA over 190 innings, while making roughly $90 million.

Google “Worst contracts in Red Sox history” and you’ll see some real head-spinners: Daisuke Matsuzaka, Edgar Renteria, Rusney Castillo, Pablo Sandoval, Carl Crawford, Matt Clement, John Lackey, Julio Lugo, and Adrian Gonzalez are the most notorious, but none of them touch the Sale contract in terms of wanton stupidity. Dice-K, Lugo, and Lackey each contributed to a title after they signed on; Renteria and Gonzalez each more or less lived up to their contracts, if not in Boston; Clement played well until he got hurt; Sandoval and Crawford each were in their prime and inexplicably fell off a cliff -- there is no way to foresee such disasters. As for Castillo, he was a roll of the dice by a team that was starting Johnny Gomes and Daniel Nava in the outfield. None of these contracts went according to plan, but they all attempted to fill a need and were for players who were healthy.

With the Sale contract (this does not include 2019, which was under the old contract) the Sox have thus far gotten 1 WAR and 9 crappy playoff innings for ~$55 million (thank god for the 2020 Covid discount), and still owe about $75 million more over the next two and a half seasons. The one saving grace is that the Sox almost certainly needn’t worry about him vesting a sixth year at $20 million, which would require him finishing in the top 10 in the Cy Young race.

And soon the Sox will be facing the potential knock-on effects of the Sale contract, as All-Star shortstop Xander Bogaerts is expected to opt out of his contract after this season, and All-Star third baseman Rafael Devers is patiently waiting for the Sox to extend his contract. The team signed Colorado Rockies’ All-Star shortstop Trevor Story (also coming off an injury) to take over second base and serve as a hedge against Bogaerts’ possible departure. Judging by Story’s contract, the going rate for an All- Star infielder is about 6 years for $140 million. As it stands now, the Sox could afford either Bogaerts or Devers; in a world without Sale’s contract on the books, they could afford both.

Did we mention that Sale is now 33? What a great age to be coming back from an inflamed shoulder. And Tommy John surgery. And a cracked rib. It was all completely avoidable—if they’d let him play out his contract, they could’ve signed him for way, way less, and let him prove he was healthy.

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