Will the Yankees make another memorable free agent spree out of the 2022 offseason?

Aaron Judge might be back in the fold, but that doesn’t mean the Yankees’ most complex — and potentially consequential — offseason in several years is close to over. The Judge negotiations would have been stressful enough without the palpable disappointment behind 2022’s second-half collapse and fourth straight playoff loss to Houston. It’s given this offseason a sense of urgency that’s not new but not common, either. It strikes some similarities to other critical roster shakeups during Brian Cashman’s recent tenure.

Let’s rewind to the beginning of the 2008-09 free agent period. That sense of urgency seems to have been profound after the Yankees missed the playoffs for the first time in a decade and a half, which itself followed three consecutive ALDS exits. If there was a possibility that the 2022 offseason would mark a changing of the guard, so to speak, there wasn’t any doubt it was in progress at the conclusion of Joe Girardi’s rocky first season at the helm, Joe Torre having absconded to Los Angeles.

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Not unlike when the Yankees seemingly had tunnel vision on Gerrit Cole for years before his free agency, CC Sabathia’s arrival in the Bronx early that winter was almost fait accompli. After getting burned on splashy acquisitions like Randy Johnson and Carl Pavano — and with rotation stalwart Mike Mussina riding off into the sunset on the heels of his first 20-win season — Brian Cashman wasn’t messing around with the best pitcher on the market. He also didn’t seem interested in a repeat of the depth issues that manifested in nearly 40 starts of Darrell Rasner and Sidney Ponson when Phil Hughes and Ian Kennedy were unable to contribute. He then came out swinging at another high-profile addition to the rotation, considering Derek Lowe and Ben Sheets as complements to Sabathia before settling on A.J. Burnett. Andy Pettitte was also retained on a one-year contract, rounding out the first part of a now-legendary spending spree.

Again, this was coming off the first playoff miss since the first Clinton administration, and the last time they slipped below 90 wins (2000), they at least won the World Series to compensate. Remaking the rotation in free agency without filling holes in the lineup would have been unacceptable. Of course, it so happened that just as the Yankees were set for an exodus of dangerous left-handed bats — Jason Giambi and Bobby Abreu’s contracts expired after 2008, and Johnny Damon and Hideki Matsui would do so the year after — the premier hitter of the free agent class happened to be a slugging switch-hitting first baseman. Not wanting to risk a second-tier fallback option like Adam Dunn, Raul Ibañez, or Milton Bradley, Hal signed off on a record deal for Mark Teixeira, giving the Yankees three of MLB Trade Rumors’ top five free agents of the offseason.

We all know what that got them. They found themselves at their next free agent crossroads five years later, only this time, they were the team at risk of losing the biggest prize of the offseason. They didn’t have quite as many expensive and expiring contracts as in 2008, and Hal has only grown more fearful of the Competitive Balance Tax as his tenure has gone on. This time, it seemed that signing the best hitter on the market would be mutually exclusive with filling the other numerous holes on the roster. And there were many holes — a look at the lineup cards from that 2013 team makes it easy to see why change was needed:

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Jeter and Teixeira would return to their spots in 2014, but the Biogenesis scandal had already taken A-Rod out for the 2014 season. Curtis Granderson was a free agent, CC Sabathia was no longer a front-of-the-rotation pitcher, and Andy Pettitte was retiring. As disappointing as it was that there wasn’t a world in which Hal was willing to pay market value for Robinson Canó while also solving issues like “600 plate appearances of Jayson Nix and Travis Hafner,” money was spent. Several years of declining play from the catcher and DH slots were shored up with substantial contracts awarded to Brian McCann and Carlos Beltrán, while Masahiro Tanaka was brought in to lead the rotation after posting a 24-0 record in his then-final Japanese season. And of course, while Canó was the crown jewel of the offseason, the Yankees wound up with what at the time seemed like a fine consolation prize in Jacoby Ellsbury, fresh off a run of 15 fWAR over the preceding three seasons.

That didn’t work out quite as well as the last try, for a laundry list of reasons. Still, one could argue that the process wasn’t necessarily bad, given the existence of arbitrary budget limits. Tanaka and Beltrán certainly did their jobs, and though McCann and Ellsbury were largely disappointing, a strategy of “sign the best starter, outfielder, and catcher on the market” is something I’ll try every time in response to losing a player of Canó’s caliber.

The Yankees of the 2022-23 offseason might be somewhere in between the two. In roster structure, the current team more closely resembles 2008 than 2013 as a ready-made contender looking to upgrade in the right spots and shore up depth after a succession of increasingly disappointing finishes. Like 2013, however, they must also deal with the complication of needing to decide whether to set the free agent market by retaining a seemingly indispensable star — and an owner that’s no longer willing to blindly spend more than the rest.

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Of course, they’ve already made part of their decision: where Canó walked, Aaron Judge locked himself in as (probably) a Yankee for life. The primary argument many made against giving Judge the contract he deserved was that doing so would prevent them from filling roster holes elsewhere, as was much of the case against matching the deal Canó got from Seattle. Now, we’ll get to see how much merit there is to that argument. Next season’s roster is already more set than either of the two I’ve talked about here. The potential difficulty of moving money around makes it possible that Hal’s hesitance to spend will leave Judge as the only big move of the winter.

Alternatively, there’s been enough smoke around Carlos Rodón to cloud a few rooms, and nagging whispers persist about the team’s long-speculated connection with Carlos Correa. Meeting either of their demands would make this perhaps their most consequential offseason since that 2008 splurge, particularly as the flexibility afforded by their added star power may make it even easier to find another upgrade in the outfield or rotation by way of trading Gleyber Torres or Oswald Peraza. The Yankees are already a solid contender by virtue of retaining Judge — choosing to upgrade at the top of the market at another position is what they may need to do to play with their big-spending peers.

So, a redux of the highs of 2008-09? Or another hard lesson like 2013 and beyond? The choice is theirs.