No one expected the 2016 Yankees to be any good. And they weren’t. 

They got off to a 9-17 start, and it was obvious they had to tear apart the team and play prospects, and by this time every fan wanted them to do just that. Free agency had been the Yankees’ strategy since the early 2000s and a way for the team to plug holes on their sinking ship. It worked at times as they were able to tread water, have winning seasons and reach the playoffs, but over the previous 15 years, they had won one championship. Eventually you need to start over. Eventually you need a new boat. The game had changed too much and the Yankees needed a new boat and Yankees fans wanted a new boat.

At the end of play on July 6, 2016, the Yankees were 41-43 and it looked like they would certainly be sellers at the deadline in three weeks, but ownership wasn’t on board. The Yankees then went on an 11-5 run through July 26, and were now in striking distance of a wild-card spot — only four games back — and ownership hadn’t budged on selling and giving up on the season for future seasons.

The Yankees then lost their next four games, one in Houston and a three-game sweep in Tampa Bay. It was the best thing to happen to the organization since the Astros, Indians, Expos, Orioles and Reds passed on Derek Jeter in the 1992 draft, allowing the Yankees to select him with the sixth overall pick. The losing streak pushed the Yankees out of reasonable contention, ownership gave Brian Cashman the green light to trade his veteran assets and begin the transition into “rebuilding mode.”

Andrew Miller (Indians), Aroldis Chapman (Cubs), Carlos Beltran (Rangers) and Ivan Nova (Pirates) were all traded, and Alex Rodriguez and Mark Teixeira announced their retirements. Gary Sanchez and Aaron Judge were called up to become everyday players, and in the process, Brian McCann was relegated to backup duty, which would lead to his offseason trade to the Astros. The Yankees had finally decided to show off the depth in their farm system, and thanks to that four-game losing streak at the end of July, the depth only got deeper with the top prospects they received in return.

The 2017 Yankees weren’t supposed to be good either, picked by many to finish near or at the bottom of the AL East in what was certainly going to be a rebuilding season. But there ended up being no “rebuilding.” The Yankees seemingly hit on every prospect who reached the majors and the team went from preseason dud to postseason bound, winning 91 games and putting up a plus-198 run differential.

The 2017 Yankees overcame a 3-0 first-inning deficit in the wild-card game. They overcame an 0-2 series hole to the 102-win Indians to advance to the ALCS. They overcame another 0-2 series hole to the Astros to bring a 3-2 series lead to Houston for Games 6 and 7. Ultimately, they came one win shy of reaching the World Series for the first time in eight years.

For 2018, the Yankees essentially replaced Chase Headley, Starlin Castro and Jacoby Ellsbury with Giancarlo Stanton (the reigning NL MVP), Miguel Andujar, Gleyber Torres and the Aaron Hicks who was drafted in the first round. But once again, they came up short in the postseason.

The 2017 postseason loss wasn’t crushing. Rather it was an exhilarating ride, being back at a raucous Stadium seemingly every night in October and watching a young, homegrown core get within a game of the World Series. The 2018 postseason loss, on the other hand, was crushing. After once again winning the wild-card game, and taking a game in Boston, the Yankees became the favorite in what had become a best-of-3 with two games at the Stadium where they didn’t lose. Not only did they lose both, they were embarrassed in every facet of the game, especially managing, and their rival celebrated on their field en route to a championship season.

Because of the way the season ended and the team it ended against, 2018 is viewed as a disaster, and rightfully so. But if you go back to 2016, 2017 and 2018 were never supposed to be about the Yankees. They were supposed to be about the Indians and Astros and Red Sox and Cubs and Dodgers, and they were. The timeline Yankees fans were given and expected prior to Opening Day 2016 was always 2019, these Yankees just happened to arrive early. The 2017 and 2018 Yankees gave us two unexpected years of championship contention even if it didn’t end with a championship.

Going back five years, 2019 was always circled as the first season the Yankees would truly contend for a championship, and they did. But in what has become a decade-long trend, the team fell short with inconsistent starting pitching in October coupled with an inability to get a timely hit. Two years after losing to the Astros in the ALCS in seven games, the Yankees lost to them again, this time in six games, losing four of the final five games of the series for the franchise’s fourth ALCS in 10 years. Ultimately, the first season of the Yankees’ championship window came and went without a championship.

The 2020 season was to be the Yankees’ best chance at ending their championship drought, but things started to unravel in spring training with Luis Severino going down for the season, James Paxton needing a back procedure, and the entire starting outfield of Aaron Judge, Giancarlo Stanton and Aaron Hicks expected to miss as much as the first half of the season. The shutdown in mid-March allowed for Paxton, Judge, Stanton and Hicks to heal, but it turned a 162-game season in which the Yankees’ depth would separate them from the rest of the division and likely league into a 60-game season mess. A second straight injury-filled season led to a mediocre 60-game performance from the Yankees, and in the postseason, the bats once against disappeared and Aaron Boone did all he could to eliminate his team in five games against the Rays.

The night the Yankees lost Game 7 of the 2017 ALCS I wasn’t upset. The series loss and losing both chances to advance to the World Series was disappointing, but the future of the team was so bright and so promising that losing to the eventual champions in seven games in a season in which the Yankees weren’t supposed to even be part of the postseason race didn’t hurt the way many other postseason eliminations have. Then again, I didn’t think the Yankees would be here having played three seasons with nothing to show for it other than embarrassment (2018), frustration (2019) and humiliation (2020).

The grace period with these Yankees ended after 2018. The 2021 season is now the current core’s third season in their “window of opportunity” to win a championship, and the window has closed much faster than expected. The injuries (Judge, Severino, Stanton, Hicks) and underperformance (Sanchez, Torres) over the last two seasons have led to unfulfilling seasons and with the Blue Jays and Rays one tier below the Yankees in the AL East and the Red Sox and Orioles rebuilding, the division isn’t going to be so heavily tilted in the Yankees’ favor for much longer.

There’s no more consolation prize for coming within a game of the World Series or winning 100 games and then getting blown out by your storied rival or losing in five games in the first round. There’s no more excuses and no more “next year”. These Yankees were expected to truly contend in 2019 and it’s now 2021.

The championship grace period is over. It’s long over. This October will be 12 years since the Yankees last reached the World Series and last won it. Every season with this group which doesn’t end with a championship is a missed opportunity and they have already missed too many.

Subscribe to the Keefe To The City Podcast. New episodes every Monday and Thursday during the offseason.

My book The Next Yankees Era: My Transition from the Core Four to the Baby Bombers is now available as an ebook!

‘Twas the night before Yankees Opening Day, when all through the city
Yankees fans were praying the season wouldn’t end shitty;
The Dugout and Billy’s were stocked full of liquor and beer;
Knowing in a few hours fans would be pregaming there for the first time in more than a year;

Giancarlo Stanton nestled all snug in his bed,
Telling himself he wouldn’t let having fans back at the Stadium get in his head;
Corey Kluber and Jameson Taillon tried to get some sleep with all the hype,
As tomorrow will be the first time they officially wear the Yankees pinstripes.

When suddenly on Twitter there arose a bunch of chatter,
The entire Tri-state area sprang to the Internet to see what was the matter.
Away to the computer I flew like a flash,
Tripped over my kid’s toys and knocked over the trash.

My feed was full of tweets with the Yankees’ Opening Day lineup,
There was Aaron Hicks batting third and I thought it must be a typo or fuck-up.
It wasn’t and Aaron Boone would be using the switch-hitter to unnecessarily break up the righty bats,
Completely disregarding common sense, logic, rational thinking or stats.

That’s OK, I thought, as not even Boone’s nonsensical decision making could ruin this day,
Unless he were to bring in Luis Cessa in a high-leverage situation to every Yankees fan’s dismay.
It was only the first game of 162 and much too early to get on the manager at this point in the year,
I would wait until at least the second or third game to voice my fear.

After the disappointment of ’18, ’19 and ’20, the Yankees are expected to once again contend,
Even though they let Tanaka walk and are bringing back essentially the same team because Hal didn’t want to spend.
Worried Yankee Stadium won’t sell enough $15 beers, Hal cut payroll by 50 million bucks,
If the Yankees don’t win it all, he’ll have to sit through another winter of hearing how he sucks.

Sure, the lineup is full with LeMahieu, Stanton, Voit, Frazier, Torres and Judge,
But when it came to trading for Francisco Lindor or exceeding the luxury-tax threshold, Hal wouldn’t budge.
Ownership didn’t want to use their financial resources to field the best roster they possibly could,
Thinking their long-term deals would turn into Heyward, Pujols, Price or Millwood.

So the front office went cheap in replacing Tanaka, Paxton and Happ,
Scared away from the more expensive names by the game’s fake salary cap.
Then Britton and Wilson got hurt in Tampa and they decided to pay Ottavino to pitch against them,
Early on each night the starting pitching is going to be asked to throw a gem.

Sure, with the team roster they have built the Yankees can still win,
Unless in the playoffs, Boone gives the ball to this year’s 2020 Happ or 2018 Lance Lynn.
After three years at the helm, it’s nearly impossible to trust the manager with moves in the pen,
And if he didn’t learn his lesson from last October, there will be a first-round exit again.

With at least three relievers you would undoubtedly consider elite,
If the Yankees have the lead after six when the bullpen is healthy, they should be hard to beat.
That is if Boone has figured out who should get the ball and when,
Thankfully, his comfort blanket in Jonathan Holder is no longer an option to bring in.

Now, Judge! Now, Stanton! Now, Gleyber and Gary!
Add in Voit and Frazier and the offense is once again scary.
From the netting in Monument Park to the short porch in right and over the wall,
I’m not worried about the offense carrying the team through the summer and to the fall.

The rotation is full of injury questions and depth is a concern,
But what rotation goes through an entire season without several minor leaguers getting a turn?
A couple elbow tears, a shoulder injury and lack of innings are the issues,
If Michael King is given another chance to start, I’ll need several boxes of tissues.

This October will be 12 years since the Yankees last won it all,
Enough is enough, there needs to be a Canyon of Heroes parade this fall.
I expect the Yankees to win the last game of the baseball season,
And if they don’t, their decision to be cheap better not be the reason.

One last time tomorrow, I will wish this offseason Hal had been more like his dad, The Boss,
As Gerrit Cole stands on the mound and throws his final warmup toss.
“Stepping up to the microphone is the voice of the New York Yankees,” I can hear Suzyn say,
With John replying, “Why, Suzyn, I thank you,” as the 2021  season gets underway.

Subscribe to the Keefe To The City Podcast. New episodes every Monday and Thursday during the offseason.

My book The Next Yankees Era: My Transition from the Core Four to the Baby Bombers is now available as an ebook!