Chris Sale’s Career Resurgence is Complete
Reports of his demise were greatly exaggerated
Chris Sale was just given an extension for the 2027 season for $27M with a club option for $30M for 2028. Given his two excellent seasons in Atlanta, including a Cy Young in 2024, this seems completely appropriate and I am very happy for him. His years in Boston were complicated for Red Sox fans. There was great triumph mixed in with significant disappointment.
Chris Sale was drafted by Kenny Williams and the White Sox in the 2010 June draft. He immediately pitched for the big club, and was excellent as a reliever, with a 1.93 ERA in 23.1 innings pitched. In the years that followed, he was nothing short of the best pitcher in baseball. In 7 seasons with the White Sox, he was a top 6 Cy Young finisher 5 times. Unfortunately, the White Sox were very mediocre during that time, and he didn’t get to pitch in the playoffs.
Prior to the 2017 season, GM Rick Hahn was in rebuild mode and traded Sale to Boston for Yoan Moncada, Michael Kopech, and two prospects. This was a Dave Dombrowski special. He was known for trading prospects for proven talent, and he hit a home run in this trade. Red Sox fans everywhere were ecstatic. They now had a serious rotation, including David Price and Rick Porcello, two former Cy Young winners.
In 2017, Sale had an incredible first season with the Red Sox. He made 32 starts with a 17-8 record and led the AL in innings pitched, strikeouts, FIP, and K/9. He finished 2nd to Corey Kluber in the AL Cy Young race. He followed up with a 4th place Cy Young finish in 2018 making 27 starts, going 12-4. This is when the injury problems started. On July 31 of that year, he was placed on the IL with shoulder inflammation. Upon his return he made one start and then went back on the IL with the same issue. He came back in September and pitched only 12 innings in 4 games to close out the regular season.
In the 2018 playoffs, he pitched in 5 games, starting 3. In the first 4 games, he gave up 7 runs, but the Red Sox won 3 of those games. Then, in game 5 of the World Series against the Dodgers, it was legend time. David Price and Joe Kelly pitched 8 innings of one run ball and Alex Cora handed Sale the ball for the ninth inning, leading 5-1. He stuck out Justin Turner, Kike Hernandez, and Manny Machado to end the game, all swinging. The last pitch to Machado was his signature back foot slider that had Machado on his knees with a wild swing. You remember all the final outs of your team’s World Series wins. This may have been my favorite.
Over the next 5 seasons, Sale only started 56 games due to a variety of injuries, including Tommy John surgery in 2020. After the 2023 season, with one year left on Sale’s contract, Craig Breslow became the Red Sox CBO and decided to trade him to the Braves for Vaughn Grissom. I had mixed feelings, as I’m sure many Red Sox fans did. I loved the guy, but could he overcome his injury history and be an effective pitcher again? Boy did he show us. His 2024 was nothing short of spectacular, leading the NL in wins, ERA, strikeouts, and K/9, and earning his first Cy Young award. He followed up with a very good 2025 but started only 20 games.
So, what will Chris Sale’s legacy be? The answer is he’s already one of the best pitchers of all time. Here’s how he ranks versus active pitchers:
Some of his all-time ranks are not too shabby either:
Only Roger Clemens, Randy Johnson, Greg Maddux, Justin Verlander, Tom Seaver, and Jim Palmer have more top 5 Cy Young finishes.
Chris Sale will remain a Boston favorite son and, in my opinion, needs to be recognized along with the greatest Red Sox pitchers of all time. His dominance of hitters throughout his career has been undeniable. His grit and toughness has been undeniable. I look forward to watching him pitch for years to come and will be the first one to applaud his selection as a first ballot Hall of Famer.