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.

CLEVELAND, OHIO – JULY 09: Michael Brantley #23 of the Houston Astros and Francisco Lindor #12 of the Cleveland Indians during the 2019 MLB All-Star Game at Progressive Field on July 09, 2019 in Cleveland, Ohio. (Photo by Jason Miller/Getty Images) /

2. Signing Michael Brantley to 3-Year Deal After 2018

The Yankees not signing Michael Brantley will haunt us.

In 2021, the Yankees’ outfield picture is nearly settled, with Clint Frazier poised for regular at-bats when the season begins.

But in 2018 and 2019, the Yanks worked hard to deny Frazier such at-bats at every turn. And in ’19, Frazier was truly a last resort following his early season fielding blunders, as the entire outfield succumbed to mass casualties.

You know who might’ve helped provide both a lefty change-of-pace in the batting order, improved on the Brett Gardner spot, and allowed the Yankees to weather their outfield injury storm in ’19? Michael Brantley, who instead went to the team that whipped the Bombers out of the playoffs yet again that October.

This is crazy (it’s not that crazy) but even in 2021, Brantley would be helpful, especially as it looks more and more like the regressing Gardner could be a budget casualty. After all, it’s nice to have additional good players! If your roster depth is actually good, injuries would be less of a catastrophe — less of, say, an invitation for Shane Peterson to show up, which is something that actually happened in 2018 when the Yanks didn’t have someone like Brantley.

It’s clear by now, though, that adding Brantley in 2021 would only confuse things, and — like a Charlie Morton addition — would be too little, too late. Mark my words, though: The Yankees would have a 2019 World Series ring (or at least an American League title) if the Brantley had been on the other foot.

DENVER, CO – AUGUST 30: Justin Verlander #35 of the Detroit Tigers pitches against the Colorado Rockies in the first inning of a game at Coors Field on August 30, 2017 in Denver, Colorado. (Photo by Dustin Bradford/Getty Images) /

1. Beating Out the Astros for Justin Verlander

Why on God’s green earth did the Yankees pass on Justin Verlander in 2017?

The answer has to be they didn’t believe the Astros would end up being a real rival, after they folded their way spectacularly out of the 2015 playoffs and missed the postseason the next year.

Right? It can’t simply be that they were too cheap and scared to surrender minimal prospect capital for the privilege of housing the most ballyhooed pitcher of his generation? It was a gift! A gift that ultimately destroyed us a few months later.

Don’t look a Gift Workhorse in the mouth.

Justin Verlander was so discarded in 2017 that he was available at the August waiver trade deadline. Not even the one with a high competition rate in July. When all was said and done, he cost Astros No. 3 prospect Franklin Perez, No. 9 prospect Daz Cameron, and catching prospect Jake Rogers, three people who’ve barely made a ripple years later.

But hardware lasts forever. And the Yankees could’ve, absolutely should’ve, and didn’t block the surprise hard-charging AL playoff darlings from acquiring a game-changer like Verlander. They honestly tricked themselves into thinking adding a Hall of Famer would be a gaffe. The deal materialized after midnight, and probably shouldn’t have counted anyway (will fight this to my grave, which will be sooner rather than later if we can’t win a ring), but at the end of the day, the Yanks surrendered to a rival and doomed themselves.

Remember, at the time, we all thought we were fighting for second place behind the streaking Cleveland Indians. Not at all true! The Yankees upended them in a spectacular five-game ALDS without Verlander, then lost in Game 2 and Game 6 (up 3-2) to see their World Series hopes dashed against the man they passed on.

Never has the ripple effect of a non-move been so obvious and imminent.

Though they didn’t have the benefit of systemic cheating during that regular season and postseason, the Yankees probably have a 2017 banner today if they take on one more salary and surrender fringe prospects 3.5 years ago. And if Verlander followed the same extension pattern in the Bronx, they’d be getting him back midway through 2021, Luis Severino-style, and things wouldn’t look quite so dire. They’d be the late-career Tom Brady Patriots, just trying to get right before the playoffs.

Instead, they’re the 2020 Tom Brady-less Patriots, putting N’Keal Harry and Jakobi Meyers on the mound. Up and at ’em!

SAN DIEGO, : Scott Brosius of the New York Yankees jumps for joy after the Yankees defeated the San Diego Padres, 3-0, in game four of the World Series 21 October at Qualcomm Stadium in San Diego, CA. The Yankees swept the series 4-0 and Brosius was named the Most Valuable Player of the series. (ELECTRONIC IMAGE) AFP PHOTO Don EMMERT (Photo credit should read DON EMMERT/AFP via Getty Images)

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