Don Mattingly, who spent a remarkable 13 full seasons in a Yankees uniform, holds the distinction of being the greatest Yankee never to set foot in a World Series. In contrast, Aaron Judge has reached the American League Championship Series on three occasions, a feat that eluded Mattingly throughout his illustrious career. Nevertheless, Aaron Judge’s seven seasons with the Yankees signify that he has already traversed more than half the distance to becoming a figure akin to Mattingly in terms of his tenure with the team.

Now, in missing the postseason, Aaron Judge finds himself in a situation akin to Mattingly’s for the entirety of his career until October of 1995. It was during that postseason when Mattingly, even in the twilight of his career, faced off against future Hall of Famers like Ken Griffey, Jr., Edgar Martinez, and Randy Johnson. In that series, Mattingly showcased what October had been missing all along by not including him in its storied history.

Aaron Judge’s career and the Yankees’ trajectory

Aaron Judge made his rookie debut in 2017, a year when the Yankees led the Astros in the ALCS three games to two before eventually succumbing. Their defeat was attributed, in part, to Aaron Judge’s slump at the plate, a struggle that was mirrored by his teammates in pinstripes. Ultimately, the Yankees lost the series in seven games. Two years later, they were defeated in six games by the Astros. Then, in the following season, they endured a harsh sweep.

Currently, Aaron Judge finds himself only one season into a staggering $360 million contract—the most significant financial commitment the Yankees have ever made to a single player. It’s evident that he is firmly anchored within the organization. However, questions linger about the Yankees’ trajectory. In contrast, teams like the Braves have achieved championship success, and even youthful Orioles have showcased their potential at the apex of the American League East. In light of this, either Hal Steinbrenner or Brian Cashman may need to reassure Aaron Judge that he will have the opportunity to partake in a World Series before his prime years wane away.

If Steinbrenner and Cashman attempt to convince themselves that the Yankees’ slump to fourth place in the East was merely the result of unfortunate circumstances, they are deluding themselves. They forget the lofty standards that were once the norm for their team—a stark contrast to the Yankees’ current reality, having gone 14 seasons without a World Series appearance, despite investing over $4 billion in baseball players.

Should Steinbrenner succumb to Cashman’s persuasion that the analytics department shoulders the blame for the team’s performance, with some members serving as scapegoats, similar to former hitting coach Dillon Lawson, the Yankees’ owner would appear more out of his depth than ever before?

Much is made of Cashman’s track record with the Yankees, and it is undeniably impressive, even though he initially inherited teams that he did not personally construct. However, despite their unbroken streak of winning seasons and three appearances in the Final Four within the last seven years, the Yankees have not held the distinction of being the best team since 2009. They continue to attribute their 2017 postseason disappointment to sign-stealing, yet no one has adequately explained how sign-stealing can account for the Yankees’ meager one-run output in Games 6 and 7 of that year.

A complete decade has passed since the days of Derek Jeter and Mariano Rivera, integral members of the legendary Core Four that underpinned the Yankees’ last dynasty. Their deeds and identities have grown as distant and as irrelevant as evoking the names of icons like Mickey, Whitey, and Yogi from the ’50s and ’60s. Looking ahead, their storied history offers no more assistance to the Yankees than Cashman’s own track record.

Aaron Judge has high hopes from the Yankees

Aaron Judge himself, serving as the team’s captain, articulated the following sentiment in a recent interview with NJ Advance Media:

“There are a couple of quick fixes and then there’s some other things that are going to take some tough conversations and some long talks with a lot of people in the room. I won’t get into that right now. I can sit here and talk about it all I want, but it’s about us sitting down and getting it figured out and getting it done. It’s going to take a lot of people. You have a season like this, it opens eyes of some people. You can mask some things by winning. This season puts us in a different light. It’s going to give us a chance to get some things right.”

It’s important to acknowledge that the responsibility for setting things right doesn’t fall on Aaron Judge’s shoulders, nor does it rest on Aaron Boone’s. The onus lies squarely on Cashman’s shoulders—he’s the one who greenlit the trade for Giancarlo Stanton, absorbing what remained of Stanton’s hefty $300 million-plus contract from the Marlins. He’s also the mastermind behind Aaron Hicks‘ seven-year deal and the acquisitions of Josh Donaldson and Joey Gallo, to name just a few decisions that have raised eyebrows in recent seasons.

The heart of the matter revolves around the Yankees’ inability to develop and maintain a frontline starting pitcher since the days of Andy Pettitte, another illustrious member of the Core Four. The team has aged and slowed down, while their division rivals have become younger and faster. If the Yankees believe that their late-season victories offer any glimpse into what could have been, they’re deceiving themselves. In reality, they stopped playing meaningful games as early as August, despite defeating some playoff contenders along the way. It was all essentially part of what the legendary Marv Albert used to refer to as “extended garbage time.”

So, the Yankees managed to avoid finishing in last place, unlike the Red Sox who repeated that fate. However, the Red Sox have claimed four World Series titles since 2004, whereas the Yankees have clinched just one in the same timeframe. Even as recently as two years ago, the Red Sox were on the cusp of another championship.

While Aaron Judge isn’t growing any younger and has had his share of injuries this season, he remains a cornerstone figure. Gerrit Cole, another marquee player on the team with a massive $300 million-plus contract, will celebrate his 34th birthday next season. It’s legitimate to question how much prime time he has left. To reiterate, Aaron Judge is here to stay. However, Cole holds the right to opt out after the upcoming season.

Ultimately, it’s Aaron Judge who holds the key. The Yankees’ present and future are built around him, and he has committed the remainder of his prime years to the team. He’s been a Yankee for seven years now, marking the midpoint on his journey to becoming another legendary figure like Don Mattingly.

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