Here We Are, Again.

Charles Lippolis
4 min readOct 14, 2020
Photo by Christian Petersen/Getty Images

For the 11th straight season, the New York Yankees did not appear in, or win, MLB’s World Series. This feeling has become all too familiar to Yankees fans, but 2020’s dismissal conjured a new level of hollowness, disappointment, and frustration. This was supposed to be the year — but yet — here we are again.

Of course, 2020 presented unique challenges of it’s own, but the Yankees were a team constructed to handle any bump in the road. They exhibited extreme focus all season; serving as an example of discipline and togetherness while many franchises across sports were overwhelmed by the immense pressure superimposed on our world by the COVID-19 pandemic.

However, external stressors didn’t play a role in the downfall of the 2020 New York Yankees. Injuries again factored into their struggles; with Judge and Stanton missing significant time during the regular season, Paxton and Kahnle having their seasons ended prematurely, and Luis Severino missing the 2020 campaign all together. Even so, the Yankees got to show off the depth of their organization in 2019, surely they could build upon their success in 2020, right? Wrong. The “Next Man Up” club was left on the field in Houston last season, as Mike Tauchman, Mike Ford, Tyler Wade, and Thairo Estrada all failed to build upon the success they had during last years magical run.

This left the club thinner than anticipated, and more reliant on the stars that were healthy. Some of them rose to the occasion; Luke Voit lead baseball in home runs, while DJ LeMahieu became the first player to win the batting title in both the American and National Leagues. Gerrit Cole anchored the rotation, while Zach Britton compiled his best season as a Yankee and served as the teams’ Player Association representative during the league’s most turbulent season in 20 years. What crippled the Yankees regular season was the key players who failed to answer the bell. Gary Sanchez put together his worst year as a pro, culminating in being benched for almost all of the ALDS. On the mound, Adam Ottavino plummeted to the bottom of Aaron Boone’s trust tree, making the loss of Tommy Kahnle even more significant to the Yankees’ bullpen plan.

As a result, it was Tampa that took the division title many thought was a foregone conclusion in July. The Yankees still made the postseason, but found themselves traveling to Cleveland to face the MVP and Cy Young frontrunners in a three game “Wild Card” series. They swept, putting the league on notice, and setting the table for a series with division rival Tampa.

At this point, everyone knows how the series went, but what I want to touch on that I think has gotten lost in the shuffle is this: winning a world series is hard.

It was said several times by Aaron Boone in the postseason, but if you told any fan in March that the Yankees would be in the postseason with a mostly healthy roster, the consensus answer would have been “I like our chances”. That was the reality, and yet, the Yankees were bounced from the ALDS in five.

This is where that frustration stems from. How did this point and lose again!? Well, like most failures in sports, the onus doesn’t fall on just one person. Between the white lines, the Yankees’ best offensive players vanished in the Postseason. That includes Aaron Judge, DJ LeMahieu, and Luke Voit. On the mound, confidence was fleeting whenever someone pitched not named Cole or Britton, making life difficult for manager Aaron Boone, who took heat for green-lighting an opener play with Deivi Garcia and J.A. Happ in Game 2. That decision clearly came from Brian Cashman and the advanced analytics team, and while we’re on the subject, Cashman’s failure to improve this team at the deadline also proved to haunt the Yankees in October.

The final factor in their losing equation was the Rays, who dominated them all season, and played ideal winning postseason baseball. They hit homers, played great defense, and featured 10+ pitchers who quieted Yankee bats. The Yankees needed a great effort to eliminate the Rays, and failed in putting forth the best version of themselves.

What does all of this mean going forward? The Championship window is still very open, but in this Baby Bomber era, the Yankees have yet to prove they can play their best baseball in October. The club has some needs going into the 2020 offseason — mid-rotation pitching, bullpen depth, middle-infield depth, and of course, resigning DJ — but what they Yankees really need to do is learn how to win in the Playoffs.

This doesn’t mean they need to change their approach as a team, rather, they need to execute when the lights are brightest. Many think their philosophy is flawed, to them I ask: what has sent the Yankees home each of the past two seasons? The Yankees have the talent, and the blueprint, but it simply hasn’t carried into October. They will be back in the postseason in 2021, but will the team that’s won 100 games in two of the past three seasons show-up? That remains to be seen.

— CL

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