What should the Yankees’ mindset be as they approach the winter?

Generally speaking, looking to the past for inspiration on how to operate a sports team is typically a recipe for disaster. Phil Jackson’s Knicks stumbled a decade ago trying to run the triangle offense that worked in the 1990s and early 2000s. A few years back, Dave Gettleman built the New York Giants roster as if it were still the late 1980s, turning a bad team into a downright disaster. And over the last two years, the Chicago White Sox ruined a promising young club when they hired Tony La Russa as manager after he had been out of the game for 10 years; whether or not concerns that he would alienate the young clubhouse materialized, in the end, it was clear that the game had passed by the old-school skipper.

And yet, looking to the past is exactly what I think the Yankees must do this winter. I’m not discussing a distant era, but the recent past: the winter of 2017-18, to be exact. Although it may not seem that way, the Yankees currently are in a place similar to where they were after losing Game 7 of the 2017 ALCS. Yes, the vibes are certainly nothing alike — then, the team was filled with hope as the Baby Bomber Era dawned, but now, despair and darkness looms as Aaron Judge hits free agency and the Baby Bomber Era ends without a ring. But purely in terms of roster construction, there are many similarities. Take, for example, the lineups and rotation that the team took into the offseason in 2017-18 and will take this year:

Note: Reminder that Aaron Judge, Matt Carpenter, Jameson Taillon, and Andrew Benintendi are free agents; for the sake of this exercise, I assumed that Anthony Rizzo will opt out, while the Yankees will exercise Luis Severino’s team option.

That 2017 squad was a good one for sure — they won 92 games and had a Pythagorean record of 100-62, after all — but the Yankees did head into that offseason with multiple holes. The entire rotation was filled with question marks, as Sevy and Jordan Montgomery were each entering just their second full season, Masahiro Tanaka and Sonny Gray had been inconsistent the year prior (despite differing playoff success), and CC Sabathia was quite clearly in the twilight of his career. The lineup, meanwhile, had a few young stars and a couple of average bats under contract, but there was a major hole at the designated hitter spot.

Although there aren’t any one-to-one matchups, the vibe feels very similar heading into this winter. Despite being inverses of each other, Jose Trevino takes on the role of the young All-Star catcher that Gary Sánchez once filled. The long-term roles that Josh Donaldson, Isiah Kiner-Falefa, and to a lesser extent even Gleyber Torres fill on this team remain hazy at best, much like Chase Headley and Starlin Castro weren’t quite part of the plan years ago. The rotation is better than its earlier counterpart, although as always, question marks remain.

So how did the Yankees approach that offseason years ago? They went on the attack, first by trying to land incoming two-way superstar Shohei Ohtani to bolster the rotation and fill the DH spot in one swoop; when that failed, they pivoted to the trade market and landed reigning NL MVP Giancarlo Stanton. Although they did not address the pitching staff until the trade deadline, they not only took concrete steps to make the team better, they went out there and got the biggest star on the market at the time.

That’s not all they did, however. First as part of the Stanton deal, they sent Starlin Castro to the Miami Marlins; three days later, they sent Chase Headley to the San Diego Padres, packaging him with Bryan Mitchell to essentially get him off the roster. Why were the Yankees willing to dump a proven, albeit unspectacular, veteran? For one reason:

In hindsight, this list looks like a cautionary tale; Estevan Florial, Justus Sheffield, and Albert Abreu have not come anywhere close to their potentials as prospects, Miguel Andújar’s promising future crumpled after his 2019 season-ending injury, and Torres has taken a definite step back since his rookie campaign. But what matters to me here is the fact that the Yankees very deliberately operated with intent here. Second and third base were being manned by decent, but far from irreplaceable, players. Sitting in the upper levels of the minors were a pair of prospects who could play those positions. At the same time the team added a superstar bat, they cleared the path* for their prospects to seize roles on the big league club early in the season.

*Technically, the Yankees began 2018 with the recently-acquired Brandon Drury at third, but since they had Andújar in-house, they were well-prepared in case of injury.

In my mind, this is the approach the Yankees need to take this winter. Dive into the deep end in free agency by bringing back Judge (and maybe Rizzo, too). Try to cut bait with Donaldson and Aaron Hicks if possible to clear roster space and remove what is, in essence, dead weight. Recognize that, although 2022 saw the end of the Baby Bomber Era, it can also be the beginning of a new one — one brought about by some combination of Oswaldo Cabrera, Oswald Peraza, and Anthony Volpe, all of whom should be playing the Major Leagues at some point next season. There may be some creative trades to work out.

The Yankees have a lot of work to do. The solution isn’t “Go big or go home.” It’s “Go big AND go home.” Just like it was back in 2017.