Speaking to reporters this weekend, Brian Cashman reiterated once again that the Yankees plan to be buyers at the deadline, although he did note that negotiations to this point have not materialized, a phenomenon that he attributed to the postponed MLB Amateur Draft. Following these comments, the Yankees immediately proceeded to get swept by the Boston Red Sox, dropping their record to 17-24 within the division and putting them in fourth place in the American League East, 6.5 games out of the first-place Red Sox.
Technically-speaking, it’s too early to call the 2021 season doomed — after all, there are still 85 games left. Both the division and the wild card, however, remain tall tasks. If both the Red Sox and Rays play at their current pace, the Yankees would need to go 57-28 (a 108-win pace) to win the East. To take the second Wild Card spot? The number of wins drops down by only two to 55, which requires a 104-win pace. On top of that, the Yankees have arguably overperformed so far this season, with a -4 run differential after Sunday night’s game that suggests the team should be under .500, not three games above it.
The last time the Yankees were in a similar boat was 2016. On July 31, that team sat 52-52 at the trade deadline, with a run differential of -33, and in the midst of a non-competitive sweep at the hands of the last-place Tampa Bay Rays. Just days prior, Cashman had sent Aroldis Chapman to the Chicago Cubs for a package centered around Gleyber Torres, although Chapman’s status as an impending free agent and Adam Warren returning to the Bronx as part of the deal suggested that the Yankees had not yet committed to the rebuild. The sweep, though, convinced Hal Steinbrenner to allow Cashman to sell off the team’s remaining assets, most notably Andrew Miller, but also Carlos Beltrán and Iván Nova.
These current Yankees are in a far different position to the 2016 squad. For starters, the 2016 squad was an old team, with seven starters — Beltrán, Brian McCann, Mark Teixeira, Chase Headley, Brett Gardner, Jacoby Ellsbury, and Alex Rodriguez — over the age of 32; the 2021 lineup, for comparison, has exactly two, Gardner and DJ LeMahieu. Secondly, the Yankees were simply mediocre in the three seasons prior to 2016; over the last three seasons, on the other hand, the Yankees have played to a 236-148 (a 99.5-win pace). For both these reasons, despite the lackluster performance, the 2021 Yankees still have the pieces to keep their window open beyond this season.
So where does that leave the team right now? Chances are, Steinbrenner won’t let Cashman become sellers, and that’s assuming that Cashman even would want to. They will be looking to add to the roster, probably in search of a starting pitcher, a center fielder, or both. But with the talent in the AL East — there’s an argument to be made that the Yankees are the fourth-best team in arguably the deepest division in baseball — this deadline should not be about the 2021 season, but about 2022 and beyond.
With that in mind, if the opportunity presents itself, the Yankees should look to leverage a major strength on their team — namely, their bullpen — to acquire additional assets to help the team long-term. At the moment, the Yankees have five relievers on the roster set to become free agents after either this season or next season: Aroldis Chapman, Zack Britton, Chad Green, Darren O’Day, and Justin Wilson. Teams often overpay for relievers at the trade deadline relative to the rest of the year, which is how Cashman was able to acquire major assets in 2016 that turned the Yankees farm system from middle-of-the-pack to best in baseball. The Yankees could unload multiple relievers and still have significant bullpen depth, thanks to the emergence of Jonathan Loaisiga and Luis Cessa.
Although it would be unreasonable for a repeat of 2016 — the fact that both Chicago and Cleveland needed relievers desperately and had not won a World Series in decades contributed to a once-in-a-lifetime perfect storm of a buyers’ market — Cashman could sacrifice some depth to help keep this core’s window open longer, much like the Cubs have tried to do this past winter. There’s many ways that this could go. Perhaps these deals are simple salary dumps, trading away high-priced relievers to give the team more room to operate under the luxury tax while offering extensions to members of the core like Aaron Judge. Perhaps this comes in the form of flipping, say, Britton and Green for the prospect ammunition necessary to pry Ketel Marte or Cedric Mullins away from the Diamondbacks or Orioles, as their status as young players with multiple years of team control means that their teams will require substantial trade packages to let them go.
For better or worse, the Yankees will be looking to add, not subtract, at this deadline. If the Yankees are smart, however, those additions should look not towards 2021 but towards keeping the window open beyond this season. To do that, the team might just need to start with a little subtraction.