The Yankees’ overconfidence has become their own undoing

October 19, 2019 was one of the toughest nights I’ve ever had as a Yankees fan. The team had battled from a 3-1 ALCS deficit to send the series back to Houston, and a ground-ball double play away from elimination, out-of-nowhere MVP contender DJ LeMahieu belted a game-tying homer to knot the score.

This was it. This was the moment the Yankees had been chasing for two years ever since their upstart 2017 ballclub got knocked out in seven games by these very same Astros. They were going to win this one, take Game 7 and go on to the World Series with an improbably successful mix of superstars and fill-ins for the many players who’d been injured along the way. The championship vibes were there.

But the Astros got out of that inning, Aroldis Chapman took the mound for the bottom of the ninth, and Jose Altuve made sure that LeMahieu’s heroics were rendered as ultimately irrelevant as Alfonso Soriano’s in Game 7 of the 2001 World Series. It was devastating to see such a remarkable season end that way.

It’s also the closest that these particular Yankees have come to delivering on the promise of 2017, and unfortunately, said 2019 success is part of the problem.

Troy Taormina-USA TODAY Sports

Even though it didn’t end in a championship, I don’t regret that season because it was the type of awesome story to behold that teams generally only get to write once in a generation. I appreciate 2009 the most, but I can respect seasons like 2019. It was wildly compelling, the cast of characters was terrific, and there was no reason to suspect that in 2023, the Yankees would still be looking for their first ALCS win since then. Unless something shocking happens, that regression will continue into 2024 and perhaps beyond.

The issue is that the Yankees took the wrong lessons from 2019 and have doubled down. Run through the roster from that season and count the number of stunning performances at the plate. The new Bronx hero LeMahieu had been a batting champion in Colorado, but in the two seasons prior, he had combined for an OPS+ of 91 (equal to what he’s posted in his deeply disappointing 2023). Gio Urshela had been a late minor-league purchase the year prior, got an opportunity when Miguel Andújar hit the shelf, and suddenly became a 3.8-rWAR player. Mike Tauchman was an even more anonymous Colorado castoff, but in just 87 games, he totaled 32 extra-base hits and 4.0 rWAR. Although Baseball Reference WAR isn’t everything, by their measures, those three players accounted for three of the 2019 Yankees’ five most valuable players.

The list goes on. Veteran Cameron Maybin went from April depth acquisition to beloved clubhouse leader with a career-best 127 OPS+ in 82 games. A sports hernia derailed Luke Voit’s 2019 second half, but until then, he’d continued his unlikely slugging heroics from late 2018 with 17 homers and a .901 OPS through the end of June. His replacement at first base, rookie Mike Ford (not a top prospect), smoothly picked up the slack with 12 homers and a .909 OPS in 50 games. A 35-year-old Brett Gardner hit 28 home runs! Brett Gardner! He was also in that rWAR top five.

Even Gleyber Torres’ performance that year was a bit of a shock. He built off his 24 homers in an All-Star rookie season in 2018 to launch 38 at age-22 in one of the greatest displays of power in baseball history by a middle infielder. Torres was a truly terrific prospect, but even then, scouts didn’t forecast this kind of power.

The miserable 2019 Orioles were not the only spark for New York’s fireworks (including Gleyber’s). For as good as they looked at the time, it wasn’t exactly some secret that the Yankees’ staff of hitting coaches had unlocked, either. The ball was juiced like it had never been before.

Plenty of fans had realized in the moment that something was up. Long balls were already up in recent campaigns, like when the Yankees slugged 267 in 2018 to break the single-season MLB record for homers that had stood for 21 years. The Twins smashed that one before the end of August 2019, en route to 307; New York was barely behind at 308 and both the Astros and Dodgers surpassed that “old” record of 267, too. The linked Ringer article in the previous paragraph has more:*

The numbers are simply astounding. MLB batters hit 6,776 home runs last season, 671 more than the previous record and more than 1,000 more than any season before 2017 ... The Orioles, Rockies, Angels, and Mariners each allowed more home runs than any previous team in history, while the Phillies tied the all-time mark.

*Others have gone on at length about the ethics behind the juiced ball and MLB’s lack of transparency. That’s not what this specific story is about though, so we’ll leave it there.

It was impressive that the Yankees had conjured a plethora of offensive contributions from surprising sources. Considering the environment though, it wasn’t as shocking as it would’ve been in other years. Once again, the problem is that the Yankees seemed to think that they’d found the secret sauce. They could get terrific results out of any hitter with interesting exit velocities, and it didn’t matter how much they struck out or that they were mostly righty hitters in their lefty haven of a ballpark. They were the ascendant 103-win New York Yankees on the cusp of winning No. 28, damn it, and they would figure it out.

The home run environment dipped a bit in the COVID-shortened 2020 but it remained above 2017-18 levels, so the Yankees didn’t suffer too many consequences that year. Tauchman, Ford, and Gary Sánchez fell off cliffs and Torres dipped as he battled separate fielding woes as the team’s new starting shortstop, but LeMahieu, Voit, and Urshela continued to thrive. Tantalizing prospect Clint Frazier finally seemed to click, too, so that only served to make the Yankees more confident in their ability to internally produce big league contributors, too.

One of the Yankees’ first instances this decade of being too clever by half bubbled up in the playoffs that year and actually on the rubber rather than at the plate. I give the Yankees full credit for moving on from longtime pitching coach Larry Rothschild even after the team-wide success in 2019. There were internal problems and despite some hiccups here and there (like Severino’s 2023), replacement Matt Blake has fairly earned strong reviews as Rothschild’s replacement.

Nonetheless, the pitching plan concocted by Blake, manager Aaron Boone, and the Yankees’ front office for ALDS Game 2 against the Rays was not a good one. Young standout Deivi García was the opener and veteran J.A. Happ relieved him in the second. It was the kind of idea that might have worked in theory, but without player buy-in, it became highly questionable. Neither pitched well and the Yankees lost. They might very well have dropped that game anyway if it was a normal start by García or Happ, but in a Division Series that went the distance and was decided by one late run, the decision cast a shadow.

In 2021, the league offensive environment dipped again and a suddenly aging Yankees team took it on the chin. This was the real beginning of their scuffles at the plate after ranking among the league leaders in OPS from 2017-20. Aaron Judge and Giancarlo Stanton did their parts with 35-homer/135+ OPS+ seasons, but as a whole, the Yankees hit .237/.322/.407 with a 100 OPS+ that featured heavy lifting from those two big boys.

Convinced that LeMahieu would at least remain a good hitter in his mid-30s if not an MVP candidate, the Yankees re-signed him to a six-year deal. His power mostly went poof, his injuries went up, and since the start of 2021, he also has a 100 OPS+ and that’s carried by a good first half in 2022. Torres again went backward as his run at shortstop fizzled out, Urshela was only fine, Frazier battled concussion issues and regressed, Andújar continued to fail in his quest to recapture his 2018 form, and the Yankees’ attempts to catch lightning in a bottle with randos as they did in 2019 went bust (sorry, Rougie). Oh, and as a bonus, García fell to pieces, too. Only one Trade Deadline reinforcement worked out in Anthony Rizzo, and the Yankees were lucky to eke out a Wild Card spot over Toronto and Seattle. They went belly-up in Boston with Gerrit Cole pitching through an injury and that was that.

Photo by Winslow Townson/Getty Images

In the buildup and completion of the 2021 season, other flaws cropped up with the Yankees’ own self-evaluation. General manager Brian Cashman has received criticism in the championship drought since 2009 for being unwilling to part with certain prospects to improve the major league club. Just to name two examples, Eduardo Núñez was kept and held up a potential midseason Cliff Lee trade in 2010, and prospect-hugging with multiple names squelched the possibility of acquiring Cole prior to his Astros breakout in 2018.

Until recently though, Cashman had done a good job of not trading away anyone he’d come to regret. He’d learned his lesson early in his career from Mike Lowell, and generally, if the Yankees traded a prospect away, there was a reason for it. It didn’t necessarily mean that the names they kept would flourish; it just meant that New York wasn’t losing Fred McGriffs, Willie McGees, and Doug Drabeks like they were in George Steinbrenner’s worst years.

From December 2020 through July 2021 though, the Yankees lost Thairo Estrada, Ezequiel Duran, Garrett Whitlock, and Trevor Stephan. Estrada has 78 extra-base hits and 4.1 rWAR (also 6.4 fWAR) in 267 games since being DFA’d in April 2021 to make room for the withered husk of Rougned Odor. Dealt in the now-ugly Joey Gallo trade, Duran is one of several Rangers breakouts during their excellent 2023, and he’s posted a 115 OPS+ in a jack-of-all-trades role. Lost in the Rule 5 Draft, both Whitlock and Stephan have impressed enough on the mound in Boston and Cleveland to earn extensions.

To be clear, I don’t expect any of these guys to rise to the levels of McGriff, McGee, or Drabek, and the jury’s still out on the players traded in 2022, but that’s four legitimate big leaguers lost in eight months. Occasionally, a Ted Lilly or Mark Melancon would get away, but for years, the Yankees were considered among MLB’s best at determining who from their own system was expendable. I can no longer say that with any confidence.

The false spring of 2022 turned out to be a microcosm of 2019, squeezed into one half. The Yankees were the best team in baseball, rip-roaring to a 61-23 start. Judge was in God Mode en route to 62 dingers and the MVP, but he was joined at the All-Star Game by five teammates. Surprising seasons were back in vogue, just like 2019, as career backup Jose Trevino and the previously washed-up Matt Carpenter made jaws drop throughout the game. Sure, Gallo, Josh Donaldson, Isiah Kiner-Falefa, and Aaron Hicks weren’t working out like the team intended prior to Opening Day, but everything was coming up Yankees otherwise!

The Yankees showed their true colors in second half, unfortunately. They had been extremely healthy in the first half and the injury bug bit them hard this time around. LeMahieu, Stanton, and Carpenter each went down with ailments that never truly went away, even when they returned to the field. All of their Trade Deadline acquisitions got hurt (some less surprising than others), and the team endured an excruciating August that whittled its 15.5-game lead on July 8th down to 3.5 by September 9th. Judge did all that he could, and the Yankees prevailed with the AL East crown.

New York narrowly avoided disaster in a five-game ALDS against the even-more-punchless Guardians and earned the right to face those hated Astros in the playoffs for the first time since the sign-stealing scandal was made public. The Yankees had talked a big game about wanting another crack at Houston to earn their right to a championship. They got the opportunity and promptly got pantsed in a humiliating four-game sweep with more of the offensive woes that plagued them in the second half.

In other organizations, the disappointments of this half-decade to date might have led to consequences. Instead, the Yankees gave Boone a three-year contract after the ugly 2021 and Cashman a four-year extension after the catastrophic ending to 2022. We don’t need the return of ‘80s George Steinbrenner with his poorly-planned moves and manager/GM carousel, but Hal Steinbrenner leans too far in the other direction toward complacency. There’s a happy medium that’s being ignored because the Yankees are still an extremely profitable business venture. (Put that on a pennant.)

This past winter, the Yankees insisted that the first-half version of 2022 was what the team really was and didn’t make any notable upgrades to the team beyond swapping in Carlos Rodón for Jameson Taillon in the rotation. To their credit, they shelled out to keep Judge — long after they should have extended him in the first place, I might add — but they were steadfast in their own brilliance. Donaldson would hit this time and that questionable trade would pay off, just you wait! Hicks and Oswaldo Cabrera were good enough to patch over the left-field void! First-half LeMahieu, Stanton, and Trevino would return! And if anyone falters, we’ll use our #NextManUp brilliance for quick fixes!

Instead, here we are on August 10th with the Yankees in last place at 59-56. The AL East is a tough assignment, but they shouldn’t be in the cellar. So forget the division, as they’re 12 games back of Baltimore; they’re 5.5 out of merely occupying a playoff spot. Barring a comeback, they’ll miss the postseason for the first time since the start of this Baby Bomber Era in 2016, and their streak of 30 consecutive seasons over .500 is in jeopardy, too.

The Yankees undoubtedly ran into bad luck with Judge getting injured by the Dodgers’ bullpen fence. But so much else has gone wrong in the Bronx that it can’t be the only culprit for this 2023 team’s woes. This team has no depth; any and all minor league talent seems to stagnate at the MLB level. If Judge is slumping or isn’t in the lineup, then there are no real threats. Stanton, Torres, and admittedly-intriguing pickup Jake Bauers can occasionally hit the ball out, but this is not a tough lineup to pitch to by any stretch of the imagination. They’ll just roll over for anyone, even moreso than the worst teams in baseball.

There’s still an avenue for the Yankees to go on a run and sneak into the playoffs, but how plausible does that really feel? This team doesn’t hit, doesn’t run the bases well, doesn’t win series, doesn’t capitalize on bad opponents, and doesn’t provide any confidence in their leadership. It’s only getting worse on that front for other reasons, as well.

We have heard time and time and time again over the past few years from Boone, Cashman, and Steinbrenner during the Yankees’ woes that how they’re currently playing doesn’t define who they are. We know that we’re better than this just because we know; never mind the fact that we’ve essentially been a .500 team for the last 200 games. We’ll smack a table if that helps! The catchphrase “championship-caliber team” has become a running joke. To paraphrase Jesse Eisenberg in The Social Network, “If you guys were a championship-caliber team, you’d have won a championship.” (Or even a pennant!)

With most of the AL East on the rise and the Astros continuing to churn out legitimate championship-caliber clubs, the Yankees are really in trouble. So although they love Boone, he might go away after 2023 as the scapegoat with only one year left on his deal. Cashman is the architect of this mess, but he isn’t going anywhere one season into his extension. And until the time comes for Steinbrenner to really self-reflect on the state of this organization, the status quo isn’t going to change.