The Contract Won’t End Well, But The Yankees Had To Sign Aaron Judge

Members of MLB front offices are tasked with developing short and long-term plans, with Plans B, C and D also at the ready should various contingencies arise. As the Aaron Judge sweepstakes finally came to a close today with the New York Yankees nosing out the San Francisco Giants and San Diego Padres at the wire, it’s worthwhile to take a look back at some of the scenarios that had to be going through Yankee GM Brian Cashman’s mind over the last couple of seasons.

The New York Yankees enter each and every season with the intent, maybe even the expectation that a World Series championship is within reach. Though they haven’t won the game’s ultimate prize since 2009, they’ve only missed the postseason three times since then, and haven’t finished below .500 since 1992. They might not be as free with their money as they were during the George Steinbrenner era, but they still annually rank among the game’s highest payrolls.

Coming out of the COVID-19 shortened 2020 campaign, Cashman likely looked at team thusly:

• Aaron Judge was the offensive centerpiece, and though his 2020 was also compromised by a calf strain, the club would need to be built around him, with his big payday two full seasons away
• Gerrit Cole was arguably the game’s best pitcher, and was under contract through 2028. The team possessed enviable pitching depth both in the rotation and pen, and projected as a potential run prevention machine.
• There were some really, really promising kids on the way on the position player side in the minor leagues. Oswald Peraza and Anthony Volpe projected as their middle infield of the future, Oswaldo Cabrera was a bat with multipositional potential, and outfielder Jasson Dominguez possessed an almost limitless power upside.

So, as early as the offseason of 2020-21, it all appeared fairly simple. Get Judge locked up, get Luis Severino healthy and keep the pitching machine humming, and keep the kids on the fast track to the bigs. They got a huge bonus as Nestor Cortes emerged as a legitimate ace in his own right and made the pitching even better than expected.

As will happen, there were other developments and decisions that had to me made along the way that didn’t break unanimously in the Yankees’ favor.

First, they had to man those infield positions with competent playoff-worthy personnel while the kids were still cutting their teeth in the minors. The Yanks opted to trade away incumbent 3B Gio Urshela to the Twins after the 2021 season, taking back Josh Donaldson and his considerable salary ($43.5M for 2022-23) in return. They also finally admitted that Gleyber Torres wasn’t going to cut it defensively at shortstop, and acquired Isiah Kiner-Falefa in a separate deal.

Now the Yanks were unbeatable in the first half of 2022 and despite a second half collapse still won 99 games, so a Donaldson/Kiner-Falefa left side of the infield wasn’t a total disaster in and of itself, but…….the money committed to those guys plus the impending presence of Peraza/Volpe left them mismatched with the best players in the 2022-23 free agent class.

Oh, and Judge, who turned down a seven-year, $200M+ deal last offseason, bet on himself and won big-time, emerging as clearly the best offensive player in baseball heading into free agency. I wrote here late last month about the predicament the Yankees faced if they let him go. They would be sitting with a pot of money and really no one truly worthwhile to spend it on if Judge had gone elsewhere. They had to sign Aaron Judge.

And as readers of Jon Heyman (a really good writer and breaker of news who lived a nightmare yesterday) will attest, they came really close to losing Judge to the Giants.

So Cashman’s preferred scenario for the 2023-24 seasons is largely in place, though they remain in the mix for other free agents. Judge is locked in, Donaldson/Kiner-Falefa might be needed for another half-season or so each, and their dollars free up at the end of 2023. The kids filter into the lineup throughout the season. The pitching staff is loaded from top to bottom. For the next handful of seasons, with Judge at or near his peak, this is a pretty fearsome group.

How do 6’7”, 280, power hitters fare as they enter their mid-to-late-30s? Well, that’s another story. Frank Howard is about the most comparable talent I can find, and he abruptly turned into a pumpkin around age 35. 2023 will be Judge’s age 31 season, so that problem is likely a few years down the road. The Yanks hope to bust their title-less streak before then.