Yankees: Is NYY championship window already closing?

SAN DIEGO, CALIFORNIA - OCTOBER 07: Aaron Judge #99 of the New York Yankees looks on against the Tampa Bay Rays during the sixth inning in Game Three of the American League Division Series at PETCO Park on October 07, 2020 in San Diego, California. (Photo by Christian Petersen/Getty Images)
SAN DIEGO, CALIFORNIA - OCTOBER 07: Aaron Judge #99 of the New York Yankees looks on against the Tampa Bay Rays during the sixth inning in Game Three of the American League Division Series at PETCO Park on October 07, 2020 in San Diego, California. (Photo by Christian Petersen/Getty Images)

Have the New York Yankees watched their championship window close before it ever really opened?

The Yankees and Cubs of the late-2010s may be forever connected the way many theorized mid-decade, but the manner of comparison might be entirely different and more depressing than any of us envisioned.

Instead of the two clubs, replete with young talent and stacked farm systems concurrently from 2016 on, battling it out in several storied World Series, the Cubs now seem destined to lose significant pieces of their core to free agency, regressing annually and only having won a singular, curse-breaking championship.

But at least they have a ring.

Though the Yankees are a bit behind Chicago on the talent departure trajectory, and operate under a different budget, it is entirely difficult to simply claim, without evidence, that they’ll be able to assemble a talent pool with similar potential immediately after building this one.

Gerrit Cole was supposed to be the final, missing piece on a championship-level rotation that would finally deliver the Yankees to the promised land…before Luis Severino and James Paxton disappeared from the equation, felled by injuries. Giancarlo Stanton, two years prior, was supposed to render the offense impenetrable, pairing Aaron Judge with a second Aaron Judge, against all odds. Instead, either Stanton or Judge has been absent from most of the past three years of gameplay, and when they do play together, their redundancies seem to be maximized, and neither can touch the other in the lineup without compromising it somehow.

Unfortunately, make that 11-6; following this observation, the team’s regular-season warts ensured we’d be speaking in negative terms following what should’ve been a narrative-swinging series victory over Tampa Bay.

Now, the Yankees have found themselves outflanked by the Astros, who took their dynastic mantle, as well as championship-level performances by the Red Sox and Rays over the past few years. 2017 was supposed to be their arrival; 2018-20 was supposed to be their territory.

Instead, we’ve seen Judge’s ceiling become lowered somewhat by his lack of availability (frankly, in much the same way Kris Bryant’s has been). 2021, which will presumably be a full age-29 season of prime Judge, must resemble the productivity of his 2017 self in some capacity, or else the Yankees will have a very difficult financial decision to make on his contract following the 2022 season.

Often ignored in this conversation, too, is that this Yankees “dynasty” was supposed to feature the greatest-hitting catcher in MLB in Gary Sanchez. Instead, we’re looking at three consecutive years of below-expectations play, as well as a repetitive postseason disappearing act. This team’s contention was predicated on a massive advantage behind the plate, which they do not have. Unfortunately, such a conversation also has to include Gleyber Torres. Once thought to be someone who’d receive an automatic extension, his defense at shortstop seems detrimental enough that a position shift might be necessary. Can he be counted on as a recipient of a guaranteed contract that’ll further restrict pitching spending?

Entering 2021 on a cost-cutting mission with over $100 million coming off the books for Masahiro Tanaka, James Paxton, DJ LeMahieu, JA Happ and others, the Yankees will retool and likely re-sign one or two of those names. They will return to contention with this core in ’21, needing a full slate out of Judge for many reasons, chief among them the ability to adequately determine how long they can afford him the same financial luxuries they did Derek Jeter. Is Judge a captain? Or is he the face of an era that cratered midway through, failing to approach expectations?

The Yankees’ window is not closed, but it will only remain open for as long as Judge’s production can reasonably be expected to exceed that of Randy Arozarena. Without an elite Sanchez and Judge, this isn’t the team most of us theorized would exist well into the 2020s. 2021 will be the season that decides whether there’s a secondary peak here, or if a 2022 sell-off looms.