When Chris Sale signed an extension with the Boston Red Sox in 2019—five more years under contract with an option for a sixth—he was one of the best pitchers in baseball.
Sale had been an All-Star for seven years running. He’d received Cy Young votes in each of those seasons and had led the league in strikeouts multiple times. His wiry frame had proven surprisingly durable; Sale had crossed the 200-inning threshold four times and had never made fewer than 27 starts in a season. All the usual pitching questions of staying power applied—Sale turned 30 a week after the deal was announced—but the extension nonetheless felt like an obvious win. It seemed clear the Red Sox had locked in an ace as the anchor of their rotation for years to come.
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