Brian Cashman made the most of what he was allowed to pursue this winter

With the Justin Wilson and Brett Gardner signings having been made official by the Yankees, it is fair to assume that the team’s winter business is complete. There likely will be no further major league signings, although adding a handful of guys on minor league deals with invites to camp is not out of the question. That being the case, it’s worth taking a step back to evaluate the job Brian Cashman has done in assembling his roster for the upcoming season.

This winter, Yankees ownership decided that the primary objective this winter was not to maximize their championship odds but instead to field a payroll below the $210 million CBT threshold, presumably to reset their tax rate for future seasons. This is a questionable decision for a team whose greatest advantage is the pure economic might it has at its disposal. Be that as it may, we have to evaluate and grade every move they made through this budgetary lens.

Last month, I criticized the Yankees and Brian Cashman for not having a more structured plan entering this offseason beyond avoiding the luxury tax. Many of the moves following DJ LeMahieu’s re-signing felt more slapdash than planned. While I still contend that Cashman could have attacked the offseason with a better delineated game plan, he nonetheless deserves praise for the creativity he showed in molding the roster and structuring contracts.

Cashman entered this offseason with roughly $35 million in space before the $210 million threshold, a paltry sum to address the glaring holes in the batting order, rotation, bullpen, and bench. LeMahieu, Masahiro Tanaka, James Paxton, J.A. Happ, and Brett Gardner were all free agents, and it was immediately clear that there was not enough room in the self-imposed budget to bring all five players back.

The first piece of shrewd business by Cashman was bringing back the team-MVP of the previous two seasons. Adding a sixth year to LeMahieu’s $90 million deal took the luxury tax hit from $18 million to $15 million, saving the Yankees $3 million to spend on other acquisitions. That $15 million AAV is especially impressive given the speculation in the media that LeMahieu could have pulled down anywhere from $20-25 million per year.

The next piece of business is one that I still have trouble squaring with, but nonetheless can be considered a win for the Yankees. Cashman replaced the rotation innings pitched by Tanaka, Paxton, and Happ with Corey Kluber and Jameson Taillon. Relying on two guys who have combined to throw fewer than 75 innings over the last two seasons to fill out 40 percent of one’s starting staff is fraught at the best of times, but given the upside and affordability of the pair ($13.25 million in 2021), Cashman did about as well as he could do to rebuild the rotation.

Cashman’s determination and savvy were highlighted in his bullpen maneuvering. In a straight salary dump, he traded Adam Ottavino to the Red Sox in only the fourth trade between the rival franchises in the last 35 years. That Cashman managed to convince a team to eat around 90 percent of the remaining $9 million left on Ottavino’s contract when brand-name relievers have been signing for $6 million and below this winter is nothing short of miraculous. He took the space previously reserved for Ottavino and turned it into two quality relievers: Darren O’Day and Justin Wilson.

Cashman saved the craftiest maneuvering for last. Truly his pièce de résistance, the Yankees GM ingeniously structured Wilson and Brett Gardner’s contracts to expose a loophole in the CBA, allowing the Yankees to defray the CBT hit across two years.

Yankees Reddit has an excellent in-depth breakdown of the machinations to achieve this here, but in a nutshell, Cashman guaranteed just enough money in Gardner and Wilson’s buyouts such that the player options for 2022 are counted as guaranteed years. Therefore, the AAV of the guaranteed money on their respective deals is stretched across two years despite both being signed to one-year deals. Consequently, instead of counting as $4 million each towards the Yankees 2021 payroll, both Gardner and Wilson will only carry a $2.575 million hit toward the CBT calculation.

I have been critical of Brian Cashman in the past when perhaps my ire would have been more appropriately directed toward ownership. The quest to avoid the luxury tax this year or any year is unnecessary and actively hampers the team. Cashman walked the tightrope of fielding a competitive team with limited resources, and I applaud his flexibility and creativity to make it happen.