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The Yankees should have bid on Jon Lester or Max Scherzer

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During the 2014-2015 offseason, two aces were available in free agency. The Yankees signed neither.

World Series - Cleveland Indians v Chicago Cubs - Game Five Photo by Elsa/Getty Images

With the World Series over, the offseason is officially underway. Attention will now be directed to hot stove news and rumors. Much commotion has already been made of the upcoming free agent class. It’s a historically weak one, especially in the starting pitching department. Rich Hill makes for a good comeback story, but it raises red flags when he’s the best free agent starter available.

This hasn’t always been the case. It just takes a cursory glance of previous offseasons to see numerous marquee pitchers available for just cash. Most notably was the 2014-2015 offseason when Jon Lester and Max Scherzer were free agents. Unfortunately the Yankees didn’t make an effort to sign either, and that decision seems to be haunting them.

Lester agreed to a six-year, $155 million deal with the Chicago Cubs on December 9th. The southpaw was coming off a 2014 campaign that saw him post a 2.46 ERA (2.80 FIP) in 219.2 innings, split between the Boston Red Sox and the Oakland Athletics. While there was some noise connecting the Yankees to Lester, that later proved to be inaccurate.

In the two years since signing with the Cubs, Lester owns a 2.89 ERA (3.16 FIP) across 407.2 innings. He’s not only led Chicago to the postseason in both years, he’s been dominant in the playoffs. His only weakness is his inability to hold runners. He’s comically bad at that. Nonetheless, Lester has been worth every penny so far.

Scherzer has been just as good as his classmate, if not better. Having signed a seven-year deal worth $210 million deal with the Nationals in January 2015, Washington had lofty expectations for the right-hander. To date, Scherzer has met them. His 2.88 ERA (3.00 FIP) makes him one of baseball’s true aces. When Scherzer is on, he’s overpowering. He also has two no-hitters and a 20-strikeout game for Washington to back that up.

Scherzer is also similar to Lester in the sense that the Yankees never pursued him in free agency. The front office was hesitant to give long-term contracts to pitchers, particularly those on the wrong side of 30. After all, it was just the previous offseason that the organization outlaid $175 million for Masahiro Tanaka, who then missed most of the second half with a partially torn UCL. They instead opted to swing a trade for the younger but lower-tier pitcher Nathan Eovaldi.

The organization made a serious miscalculation by not attempting to sign Scherzer or Lester. They’re the types of pitchers that would upgrade any rotation, but would be especially helpful to the Yankees. The New York rotation craves impact pitching. Tanaka has been an ace, but what follows is a series of question marks, at best. After all, only two of the nine starters that the Yankees used in 2016 finished with a sub-4.00 ERA.

Adding a Lester or a Scherzer wouldn’t have just been an incremental upgrade. It would have been a multiple win upgrade. Would one or the other have been been enough to fuel a postseason run? It’s tough to say without sounding like a revisionist historian. One thing is for sure, the rotation has been a weakness and adding either certainly would have helped.

Also, I would be remiss to not mention that the 2014-2015 offseason coincided with another installment of Hal Steinbrenner talking about payroll. "You all know my opinions about payroll," he said in January 2015. "Where you should be and where you really don't need to be to win championships." If Steinbrenner reached the decision to pass on Lester or Scherzer because he didn’t want to push payroll, rather than for baseball concerns, then the whiff looks even worse. The Yankees have an enormous market advantage with their cash on hand. Steinbrenner’s talks of reducing payroll doesn’t benefit the team; it further lines the family’s pockets.

The Yankees have now gone all-in on a youth movement, but the addition of Scherzer or Lester wouldn’t have been a problem. They’re the type of pitchers the Yankees should be all over, aces who are battle tested in the American League. They would have helped then and in the future. To an extent, it makes sense why the Yankees shied away, but now that looks like a mistake. They made a calculated decision, it just appears to be the wrong one.

Stats courtesy of Fangraphs.com.