Yankees Potential Free Agent Target: Jon Lester

The Yankees need to add to the rotation, there’s no doubt about that. While the team is likely to try and stay below the $210 million CBT threshold, and almost certain to stay below the second tier of tax thresholds, this means one of the routes for improving the staff is taking a flier on a veteran arm. One of those options is Corey Kluber, and the other one is former Cub and Red Sox pitcher Jon Lester.

Lester will be 37 on Opening Day, and became a free agent after the Cubs declined his $25 million option for the 2021 season. He’ll have to take a major pay cut to find a spot on a major league roster, but more pressing than that are his declining skills. After an average or so 2019, Lester saw an across the board decline in virtually every stat that mattered- his K-BB% dropped 38%, his hard contact allowed rose, and his FIP and xERA were all around his 5.16 ERA, meaning that run suppression number isn’t an accident.

If you’re looking for positives, Lester’s always been a great control pitcher, and gotten even better as his career has gone on. In 2020, Lester posted his best walk rate in five years, and stayed healthy, a hallmark of his career. Since coming to Chicago in 2015, he’s been on the IL just once, averaging 189 innings per season excluding 2020, and this year he started a dozen games and worked 61 innings, more than any Yankee starter except Gerrit Cole.

When I initially looked at Lester, based on his control, health and repertoire, I thought of the final few good seasons CC Sabathia had. Like CC, Lester is a cutter-first guy, burying pitches in on right-handers to compensate for a loss in velocity, and then pairing the cutter with a legitimately good breaking ball. Sabathia’s slider stayed effective until his final season, and Lester’s curveball is just as good, a slow, looping breaker that drops as much as any in the game, and generated a 35% whiff rate over the past two years.

The problem with that comp is, CC’s ageless wonder years came between his age-35 and 37 seasons, all three of which he posted an ERA below 4. Lester just finished his age-36 season, and his age-35 campaign had a league-average ERA. It’s not impossible to say that Lester could be another CC, it’s just unlikely — he’s older, and has thrown almost 2500 innings, so the mileage is definitely there.

Jon Lester might end up in the Hall of Fame in a few years. He’ll try to find a landing spot somewhere in MLB for 2021, I just think he’s too far gone for the Yankees to be that interested. If the team is going to take a flier on an older, declining former ace, I’d rather they try Kluber, who if nothing else is at least two full years younger.