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Questioning the Yankees’ vision for 2023 and beyond

Have the Yankees backed themselves into a corner with their decisions over the last handful of seasons?

Aaron Judge Press Conference Photo by New York Yankees/Getty Images

It’s safe to say that the 2022 Yankees season ended in humiliation for all parties involved, from the players to the executives to the fans. Thirteen years without a World Series appearance is bad enough for this particular organization — throw in their historic start to the regular season and subsequent collapse, culminating in getting swept by the Astros, and the whole ordeal would’ve been nigh-unbearable save for Aaron Judge’s record-breaking home run chase.

We’ve conducted countless postmortems on the season attempting to decipher where it all went wrong. Was it injuries? Poor management decisions? Underperformance? Last week, my colleague Jeff penned a thoughtful piece praising the investment Yankees ownership has committed to the roster this winter, concluding with a challenge to the players to perform to their potential when the games matter most.

We certainly cannot fault the Yankees for their financial outlay this winter, guaranteeing over half a billion dollars in a matter of weeks. However, I would call into question Jeff’s contention that “Whether or not the team is better on paper than its biggest competitors is a moot point — they’re close enough in talent, but that talent needs to pull through in the end.”

The bats disappeared against the Astros, but while Jeff argues that’s not the fault of the front office, I wonder if the players they have are the “right” players. Did talent fail to show up, or were they doomed to failure entering a playoff series with a cooked Josh Donaldson, hobbled Giancarlo Stanton, DJ LeMahieu, Andrew Benintendi, and Matt Carpenter, inexperienced Oswald Peraza and Oswaldo Cabrera, and punchless Isiah Kiner-Falefa, Jose Trevino, and Aaron Hicks? And by extension, I would question the at-times blind faith that fans are willing to put into Peraza, Cabrera, Anthony Volpe, Jasson Dominguez, Spencer Jones, and others when you look at the organizational failure to develop position players and maintain their skill sets at the major league level.

For the amount of hype that their top position player prospects have generated and are generating, all the Yankees have to show for the last 20 years is Judge, Robinson Canó, and Brett Gardner. Too many of the team’s blue-chip prospects either fell well-short of expectations after a couple good years in the majors, or simply never panned out at all.

The most disheartening part is that the Yankees appear poised to follow the same path that brought them to this treacherous position all over again. Rewind to the winter following the 2017 season. New York pulls off a blockbuster trade for Giancarlo Stanton, seen as the missing piece to the puzzle as the Yankees wound up one slugger shy of advancing past the Astros to the World Series. Don’t get me wrong, this is a trade you make every day and twice on Sundays — when you have the opportunity to acquire the reining MVP on the heels of a 59-homer season and the dealing team is willing to eat $30 million, you pull the trigger. But the ripple effects of that deal are still being felt five years later.

The following winter is seen as the free agent opportunity of a lifetime: two generational stars — Manny Machado and Bryce Harper — hitting the market at age 26. But with a $300 million contract already on the books (and little executive interest in adding another so soon), a new crop of prospects hitting their stride in the majors, and the opportunity to reset their luxury tax offender status, the Yankees mortgaged the future for immediate savings. Why shell out another mega-contract when Gleyber Torres had just mashed 38 home runs, Gary Sánchez looked like the second coming of Mike Piazza, Jackson Frazier (née Clint) was knocking on the door, and Miguel Andújar had just finished second in Rookie of the Year voting after breaking Joe DiMaggio’s rookie doubles record?

Toronto Blue Jays v New York Yankees Photo by Mike Stobe/Getty Images

Well, where are Torres, Sánchez, Frazier, and Andújar now? Gleyber at least looks like an everyday regular, but remains miles off the player who looked like he would be a perennial All-Star through his first two major league seasons. Sánchez and Frazier are currently out of jobs with a month to go until spring training, while was claimed by the Pirates off waivers after appearing in just 114 games over the last four seasons. All four saw their hit tool degrade significantly within a few years of reaching the majors.

Which is why I question the belief in this newest crop of hitting prospects. Not in the prospects themselves, but in the Yankees’ ability to guarantee skills maintenance, much less development upon establishment in the majors. They’ve placed an enormous onus on the shoulders of their top prospects for an organization that has not exactly seen their youngsters flourish in this championship window.

Fast-forward to today and wouldn’t you know it, the three positions with the most uncertainty — shortstop, third base, and left field — are the three positions they neglected to upgrade via free agency and trade because of their desire to offset the large contracts on the books with surplus value reaped from their graduated prospects playing for the league minimum.

Yes, the bats were overmatched against the Astros. But are we really prepared to rely on Volpe, Peraza, and Cabrera to get them over that hump? Why not sign a Carlos Correa? Why not trade for a Bryan Reynolds? Proven production goes a lot further in guaranteeing future success than a handful of lottery tickets.

Not too long ago, majority owner Hal Steinbrenner relayed his belief that “you shouldn’t have to have a $300-million payroll to win a championship.” How ironic, then, that the Yankees currently field a $291 million payroll and at best made a lateral move from the group of players that got swept out of the ALCS by the Astros, with regression almost certain to offset the added value Carlos Rodón brings. At what point does the blame shift away from the players and onto the front office choosing said players?