Yankees: 3 missed opportunities that doomed NYY for 2021

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The Yankees passed on these moves years ago, which have doomed them now.

All the pressure in the world remains on the Yankees entering 2021, suddenly juggling a budget crisis while still trying to justify this entire era by capturing their first World Series since 2009.

But what if the roster didn’t have the glaring current holes it’s saddled with due to previous proactivity? And what if the Yankees had, say, won a ring or two in 2017 and 2019, rendering this current pressure-packed conversation largely irrelevant?

Say no more!

These three non-moves doomed the Yankees to ALCS-and-out over the past several years, and could’ve also helped out the 2021 crew significantly if they’d been completed as dialed.

Instead, the flip side of these maneuvers all helped the Yankees’ rivals towards their celebrations, or changed the World Series trophy’s hands several times in the interim.

Bottom line: Mistakes were made.

MINNEAPOLIS, MN – JULY 15: National League All-Star Anthony Rizzo #44 of the Chicago Cubs and American League All-Star Jon Lester #31 of the Boston Red Sox pose for pictures before the 85th MLB All-Star Game at Target Field on July 15, 2014 in Minneapolis, Minnesota. The American League defeated the National League 5-3. (Photo by Bruce Kluckhohn/Minnesota Twins/Getty Images) /

3. Signing Max Scherzer or Jon Lester After 2014

The Yankees were splurging at that point. So why not a long-term splurge?

After the 2013 season ended, likely the most boring year in modern Yankees history and one in which the not-highly-thought-of Red Sox ran roughshod through the AL East and captured a surprise title that — if given truth serum — they’d admit wasn’t in their plans, the Bronx Bombers had moves to make.

This resulted in an all-in offseason featuring the type of win-now reinforcements a good team usually makes in an attempt to become great.

Unfortunately, the Yankees were a brutally bad offense and an empty pitching staff looking to distract onlookers with big names.

Some moves worked — we’d wager that most fans would go after Japanese import Masahiro Tanaka again, the only forward-thinking move in the bunch. But instead of bringing Robinson Cano back or pocketing some coin for the years to come, the Yanks signed Brian McCann to a five-year, $85 million deal, Carlos Beltran to a three-year pact, and Jacoby Ellsbury to the Contract That Must Not Be Named.

All of these maneuvers were defensible if the Yankees planned to be a big money monolith for the next decade. Except the offseason after 2014, in which Tanaka went down with his mysterious elbow injury (seriously, how did that hold up for his entire contract?) and the other three men performed decently, but not admirably, the team decided to do next to nothing. So…2014 was it! Solid plan! Monster austerity spending one year, aimless blinking the next.

Of course, the 2015 team somehow limped into the Wild Card Game, but their fate might’ve been better if they’d simply ponied up the requisite dollars for one more deal. Both Jon Lester and Max Scherzer were available that offseason, and if the Yankees had simply signed one of them, their next six seasons would’ve been very different — heck, Scherzer would be riding off into the sunset, ready for his final year in pinstripes in 2021.

Instead, both men won rings with their national league teams, and the Yankees didn’t get any better until Aaron Judge arrived with a chemistry boost in 2017 — when they were still very much one pitcher short.