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The Yankees find themselves in the same position as two years ago

After the 2019 season, the Yankees had a good roster but an obvious need, much as they do now. Will they repeat the past and reel in another big fish?

American League Division Series Game 2: New York Yankees v. Tampa Bay Rays Photo by Alex Trautwig/MLB Photos via Getty Images

There’s a buzz in Yankeeland right now. That gentle hum comes in the form of pretty consistent rumors about the team’s crucial upcoming winter. With the Yankees faced with numerous important decisions and expected to be active on the free agent and trade markets, those in the know are already linking the club to the likes of Corey Seager and Carlos Correa, to Matt Olson and Anthony Rizzo.

This stands in stark contrast to the buzz around the Yankees a year ago, when the scuttlebutt had them doing everything in their power to avoid splashing too much cash and dipping under the luxury tax threshold. It’s almost a breath of fresh air, to return to a time when the Yankees are expected to be spenders, rather than penny-pinchers.

But the Yankees have found themselves in this position before. In fact, the Yankees enter this winter in almost exactly the same spot as they did two years ago. That was the winter that saw them break records with the Gerrit Cole contract. Whether they act in the same manner this time around will determine the arc of the entire offseason.

See, after the 2019 season, the Yankees found themselves with a strong roster, one that had made the playoffs three years in a row and won 103 games the season prior, but one with an evident hole. The lineup was stacked, and the bullpen was fierce as ever, but with Luis Severino a massive injury question mark and Masahiro Tanaka aging, it was clear to anyone paying attention that the Yankees were in desperate need of a frontline starter.

As fate would have it, the free agent class that winter appeared specifically designed to treat what ailed the Yankees. It featured Cole at the top of the class, flanked by Stephen Strasburg fresh off a World Series MVP, as well as attractive secondary targets like Zack Wheeler and Hyun Jin Ryu.

The Yankees were presented with the easiest possible puzzle. In possession of a roster with one clear need and a free agent class designed to fill it, all they had to do was spend the money required to grab that last big piece and plunk it right in the middle of the otherwise-solved puzzle. On this occasion, Hal Steinbrenner obliged, and $324 million across nine years convinced Cole to put pen to paper.

Just two years later, the Yankees find themselves at the same point. They still possess a good roster, one that’s made the playoffs five years in a row and managed to win 92 games last season in spite of a calamity of injury, illness, and underperformance. But again, it’s a roster with one readily apparent need: the only true shortstop on hand is Tyler Wade.

And once more, a Yankee team with a shockingly clear weakness enters a winter coincidentally designed to address that particular weakness. Not one, not two, but five in-prime shortstops head this class. Carlos Correa and Corey Seager fill out the top-two on nearly every public free agent ranking, with Marcus Semien close behind, and Trevor Story and Javier Báez lurking somewhere in the top-12 or so.

Just as signing Cole to plug into a rotation dying for an ace was the painfully obvious move two years ago, plugging Correa or Seager into a lineup desperate for an actual shortstop is equally obvious. In 2019, Steinbrenner simply chose to press the button and made Cole a Yankee. Steinbrenner can all but ensure this offseason is a success by just running it back, and putting a superstar shortstop in pinstripes.

Of course, even if the main question the Yankees face now is strikingly similar to the one they faced in 2019, not everything about their position is the same; two years have passed. As our Josh Diemert is keen to point out, championship windows are wont to close at a moment’s notice. The Cubs went from world-beaters to also-rans in just a few years. The Nationals’ title team evaporated on contact. Two more seasons with this core has left everyone a little older, a little more expensive, and the team a little closer to seeing their window slam shut.

But some windows remain open. The Astros have continued to contend seven years out from their initial foray back into the postseason. The Dodgers are a perpetual motion machine nearing a decade of constant excellence.

Signing a Correa or Seager is a winning move that can help ensure the Yankees are more Dodgers than Cubs. There used to be a common sabermetric refrain, about Mike Trout and the Angels. Peak Trout was so good that, as the saying goes, the Angels needed only to gather an average team around him to make the playoffs. None of Correa/Seager, Cole, or Aaron Judge are as good as Trout, but assembling such a trio would put the Yankees in a similar spot as the Angels. Even surrounding a Seager/Cole/Judge core with a supporting cast of literally average players would likely make the Yankees a playoff team for years to come. The presence of Giancarlo Stanton, Joey Gallo, and a deep pitching staff should make for a supporting cast much, much better than just average.

The Yankees have a complicated offseason ahead of them, with tough questions to answer about their catcher, first baseman, center fielder, and on down. But in truth, this winter also couldn’t be more simple. They have one obvious need, and multiple excellent options to fill it, just as they did two years go when they tabbed Cole as their savior. All they have to do is follow the same script and get their man.