Yankees’ Underwhelming Offseason Has to Lead to Overwhelming Season

Yankees fans have no choice than to believe in roster they've been given

This offseason sucked. There’s no other way to look at it. The Yankees had an opportunity to completely upgrade their roster, change the comfortable-with-losing culture their manager has instilled within the clubhouse and become the clear favorite to win the American League and get back to the World Series. They instead chose to make marginal-at-best roster upgrades, extend the manager for three more years (with an option for a fourth year) and you would have to be a Steinbrenner, a good friend of Brian Cashman or the biggest Yankees apologist of all time to consider them the favorite, as of now, to win the pennant.

Unfortunately, as a Yankees fan, the roster the Yankees have put the together is the one I have to root for. After months of writing and talking about the missed opportunity the franchise purposely created for itself, this week I need to put that aside and pray that what changes the Yankees did make will be good enough to win in 2022.

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. (A trade in which the Yankees would pay McCann to beat them in Game 7 of the ALCS). 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 (to use Aaron Boone’s favorite word), 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 six 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 (I’m trying to use this word as often as Boone does in one of his postgame press conferences), 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 Boone did all he could to eliminate his team in five games against the Rays.

The Yankees were the odds-on favorite to win the American League in 2021. They got off to a 5-10 start, were 12-14 at the end of April and 41-41 on the Fourth of July. A 13-game winning streak in July and August saved their season, only to be followed by losing 12 of 15 in August and September. The odds-on favorite to win the AL finished fifth in the AL, third in their own division and their postseason was over after nine innings.

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 four seasons with nothing to show for it other than embarrassment (2018), frustration (2019), humiliation (2020) and disaster (2021).

The grace period with these Yankees ended after 2018. (Unless you’re Cashman and believe the Yankees actually won the 2017 World Series, then the grace period is still going.) The 2022 season is now the current core’s fourth season in their “window of opportunity” to win a championship, and the window has closed much faster than expected, if it’s even still open. The season-crippling injuries to Severino, Judge, Stanton, Hicks and Luke Voit coupled with the underperformance of players like Sanchez, Torres, Sonny Gray and James Paxton over the last four years have caused the championship drought to continue. Only two players remain from the Game 7 lineup from the 2017 ALCS: Judge and Hicks.

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 or eeking your way into the playoffs on the final pitch of the regular season. There’s no more excuses and no more “next year”. These Yankees were expected to truly contend in 2019 and it’s now 2022.

The Yankees set themselves up for the most second-guessed roster construction of all time if their 2022 creation doesn’t work out. Before and after lockout, they passed on every star, passed on every starting pitcher and passed on the A’s firesale. At the team’s end-of-the-season press conference on Oct. 19, Cashman said he would be making “upgrades” and that he would use the “free-agent marketplace” and “trade market” to acquire the available “legitimate options” for said upgrades. The “legitimate options” will be playing for the Dodgers, Braves, Rangers, Mets, Red Sox, Twins and Padres in 2022. None of them will be playing for the Yankees.

This is the team Yankees fans were given to root for and to get behind. This is the roster we are being asked to support and follow and invest our time and money into for the next six (and hopefully seven) months.

A year ago on Opening Day, Gerrit Cole couldn’t get through the sixth inning against the Blue Jays (a trend that would continue all season for the Yankees’ ace against the Blue Jays, Rays and Red Sox). Boone went to Nick Nelson, of all relievers, for the 10th inning in a 2-2 game with the automatic runner on second, and he promptly allowed Randal Grichuk to break the tie with a double. Trailing 3-2 in the bottom of the 10th, Boone’s No. 3 hitter Hicks took three pitches, all strikes, for the first out and Stanton took two strikes then swung through the third pitch of his at-bat before Torres struck out on five pitches. I wish I had turned off YES after the last pitch of that game and not turned it back on again for the rest of the season. Hundreds of wasted hours, dangerously high blood pressure, heartache and mental and physical fatigue would have been avoided.

I don’t want to look back on the 2022 season like I do the 2021 season and regret having wasted so much time. With the roster Cashman has created, it’s a real possibility. It’s not just a possibility, it’s the most likely outcome. For now, I will do my best to believe this roster can win. As a Yankees fan, I don’t have a choice.

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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!