World Series or Bust Once Again for These Yankees

Yankees can't waste another season in their championship window of opportunity

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 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 and the Yankees needed a new boat. 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 expectation was that the Yankees would go out and acquire more patches for their old, under-performing, beat-up roster.

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 what the Yankees were calling a “transition”.

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. There ended up not being any transition or 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. Once again, they came up short in the postseason.

The 2017 postseason loss wasn’t crushing. 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 falling into and 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 home games, 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.

The 2019 season could have and probably should have been a disaster. When you set the single-season record for most players placed on the injured list, you’re not supposed to win your division or 103 games. You’re not supposed to sustain success with backups becoming everyday players and backups to the backups carrying the team for weeks at a time. The Yankees got 49 plate appearances from Miguel Andujar, 18 games from Giancarlo Stanton and 59 from Aaron Hicks; Gary Sanchez missed six weeks and Didi Gregorius and Aaron Judge each missed two months; Luis Severino pitched 12 innings and Dellin Betances faced two batters; James Paxton and Brett Gardner made trips to the injured list and CC Sabathia made several. Despite these injuries and more, the Yankees won the AL East and the ALDS.

The ALCS was a different story, a disappointing story. The Yankees won Game 1 won in a blowout in Houston, but lost the next three and four of the last five games of the series to lose to the Astros for the second time in three years. It was the Yankees’ fourth ALCS loss in 10 seasons and it came on a walk-off home run after the Yankees had tied Game 6 in the ninth inning in the most improbable way.

This season represented the Yankees’ best roster and best chance at winning a championship with this group. Their lineup was as deep as usual and their pitching staff so bolstered Masahiro Tanaka would be their No. 4 starter. Then the shutdown happened, the season was condensed to 60 games and the injury bug ravaged the Yankees before and during the season for a second straight year. They managed to do enough to get into baseball’s ridiculous eight-team playoff field and then beat the league’s top pitcher this season and overcame their own manager’s ineptitude to reach the ALDS and the San Diego bubble.

It’s nearly impossible to predict who will and won’t perform in the postseason, with the goal being to get there and then hoping things go your way. The Yankees achieved that goal, managing to do enough to get into baseball’s ridiculous eight-team playoff field and then beat the league’s top pitcher this season and overcame their own manager’s ineptitude to reach the ALDS and the San Diego bubble.

The championship grace period for the organization is over. It’s been over. It’s been more than a decade of Octobers since the Yankees last reached the World Series and last won it.

The grace period for these Yankees is over as well. Depending on your viewpoint, this is either this Yankees core’s first, second, third or fourth season in their window of opportunity to win a championship. There’s no more consolation prize for coming within a game of the World Series and losing or having another 100-win regular season and getting eliminated in the ALDS or reaching the ALCS and failing to get to the World Series. Every season with this group which doesn’t end with a championship will be a missed opportunity.


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