Assessing the Yankees’ trade deadline priorities

Entering the 2021 trade deadline, the Yankees are at a crossroads. At three games over .500 with a negative run differential, especially coming off of a brutal sweep at the hands of the Red Sox, the team looks as far from a playoff team as it has all year. Certainly, they’ll want to keep their chances of contending in 2022 alive, considering it’ll be Aaron Judge’s final year of arbitration-eligible pay before reaching free agency. Also, they’ve already got a third of a billion dollars committed to the triumvirate of thirty-plus-year-olds in Gerrit Cole, Giancarlo Stanton, and DJ LeMahieu. Still, they’ve got a long way to go just to reach the playoffs, now six-and-a-half games out of the division lead and five back from the second Wild Card spot.

If the team takes an honest look in the mirror and decides they don’t have a chance to compete with the roster as currently constructed, they absolutely need to sell off what they can in order to optimize their chances of winning next season. However, so many of their once valuable trade chips have bottomed out, with Deivi García struggling to hang in Triple-A (8.80 ERA), and former standouts Gleyber Torres and Miguel Andújar bolstering their cases that their rookie campaigns were more exceptions than the rule. What once could have netted them an All-Star caliber contributor like Trevor Story or Luis Castillo might not be able to get them anything anymore.

Their next best bet to recoup value for expiring assets is probably to just shed as much money as possible in the hopes of splurging on a free agent next offseason, likely a shortstop like Story, Corey Seager, or even Marcus Semien. The most direct route to dumping cash can’t be Cole, Stanton, or DJ — not only are those contracts too big to move, especially in Stanton’s case, but the Yankees also can’t afford to double-cross their most recent pair of signees if they hope to maintain pole position as a free agent destination in the future.

More likely, is that they move away from at least one of their pair of deluxe relief arms while they still hold value. While Britton’s pitched poorly when healthy, and mostly, he hasn’t been, he still holds the pedigree of one of the best relievers in the recent history of the American League, having held a sub-2.00 ERA in each of the past two seasons. Due $13 million this year and $14 the next, some contending team is likely willing to pick up that tab for his services if only in exchange for the financial relief his departure would bring the Yankees.

Even more significantly, the Yankees could decide to sell Aroldis Chapman to a contender, again, albeit for a lesser return than they did the last time. In 2016, the Yankees traded Chapman to the Cubs in exchange for Gleyber Torres in what still appears to have been a rare win-win trade. Chapman helped the Cubs win their first World Series in 108 years, and the Yankees got a blue-chip prospect who eventually had two massive offensive seasons for them. While he’s had a rougher couple of weeks than his sterling start to the 2021 campaign, Aroldis Chapman is absolutely still one of the premier closers in baseball and could easily net some decent return with $35 million left on the books between this season and next. If they choose to do so, the Yankees could turn the money they’ve committed to Chapman and Britton into a marquee free agent, and maybe even a prospect or two.

If the Yankees decide to push their chips into the pot this season, there are avenues for them to improve immediately. Although pitching has been their greatest concern in the past, their staff has had a successful season on the whole despite some recent stumbles. Offensively and defensively, however, the team’s play has been poor all season long. They’ve gotten basically nothing from their rotating cast of left-fielders, and Torres’s play has been one of baseball’s biggest disappointments, especially after DJ has picked it up as of late. Ideally, they could put together a package enticing enough to net someone to plug any one of those gaps.

The franchise may have already reached a conclusion internally, but the Yankees do need to decide if they want to keep the window open this year, or close it to save some oxygen for next. If they keep their bullets chambered, they may have some to expend this offseason, but it’ll make the latter half of the 2021 campaign at least as gruesome as the first half has been.