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The Yankees Were Ahead of Schedule. Now They’re Full of “What Ifs?” and Staring at an AL Death Pit.

After a walkoff loss to the Astros, the Yankees have gone an entire decade without a single World Series appearance for the first time since the 1910s. Now what?

League Championship Series - New York Yankees v Houston Astros - Game Six Photo by Elsa/Getty Images

In the end, of course, one of the superpowers had to lose. Such is the nature of zero-sum playoff baseball, and 103 regular-season wins, a summer full of player development triumphs, and an ALDS sweep weren’t enough to save New York from playoff elimination. In Game 6 Saturday, the Astros beat the Yankees 6-4, and for the second time in three years, New York’s season ended in Houston as the home team celebrated a World Series trip.

A series this close—the final runs totals were Houston 22, New York 21—is bound to generate a winter’s worth of rued moments and if onlys, and this six-game loss is no different. If only Adam Ottavino hadn’t hung a breaking ball with his first pitch in Game 2, the Yankees might have taken a commanding 2-0 lead going back to New York. If only Didi Gregorius’s warning-track fly ball with two men on base had traveled an extra few feet—say, an extra 4.5 feet, per the playoffs’ dejuiced ball—the Yankees might have beaten Gerrit Cole to win Game 3. If only they had hit even a smidge better than 6 for 45 with runners in scoring position in the series, they might have scored some extra crucial runs, and if only Aroldis Chapman hadn’t lost the strike zone and then threaded a slider to José Altuve in the ninth inning of Game 6, they might have completed a raucous comeback in the game and series.

Overall, the Yankees had a better batting average than Houston in this series. They had a better on-base percentage. They had a better slugging percentage. Yet Houston won both of the week’s close games at home via walkoff, and now the Astros return to the World Series. New York is left to lament a rollicking-fun season gone awry too soon—for the first time since the 1910s, the Yankees went an entire decade without a single World Series appearance.

New York’s loss in Game 7 in Houston in the 2017 ALCS was a disappointment, of course, but it represented an optimistic turn for a franchise that, just a year prior, had sold at the trade deadline in decidedly un-Yankee-like fashion. The Yankees were back, and they presumed to contend for a while. And contend they have, winning at least 100 games in consecutive seasons, only to lose to another AL superteam in the playoffs every time. In 2019, even after a triumphant regular season, the disappointment at another postseason defeat overwhelms.

For the first six months, this Yankees season was an unimpeachable success. Despite a record-setting rash of injuries, they won the division for the first time since 2012. They led the majors in runs and hit 306 homers, and finished one shy of the Twins for the new MLB record. And they proved incredibly adept at turning Quad-A players into major-league staples. When Miguel Andújar got hurt, Gio Urshela grew into a two-way stud. When Aaron Judge, Aaron Hicks, and Giancarlo Stanton went down at various points, Mike Tauchman did the same. Gleyber Torres and DJ LeMahieu gave the Yankees two legitimate stars in the infield; Gary Sánchez bounced back after a woeful 2018.

Yet against Houston, the lineup faltered, particularly after the top four. The unbeatable bullpen shuddered and shook. And a summer of inactivity was exposed: After letting the trade deadline pass without a single rotation addition, the Yankees were left to resort to a bullpen plan in an elimination game—relying not just on the core relievers, but on the lesser arms and longmen of the pen.

The Astros are every bit as super as the Yankees, just as the Red Sox were every bit as super last year, and just as the Rays might be every bit as super next year, with their 2019 surge and best farm system in the majors. The question for New York this offseason, above and beyond the if onlys and backward-looking laments, is how to improve even more before next season for another try in the death pit that is the modern AL playoff bracket.

On offense, shortstop Didi Gregorius is a free agent, and given the Yankees’ veritable fleet of capable infielders—they could easily slide Torres to short and play LeMahieu at second every day—it seems likely that the fan favorite has played his final game in pinstripes. The club will have to make a decision on free-agent outfielder Brett Gardner, a lifelong Yankee who enjoyed a career-best year at the plate at 35. A pair of veterans who joined the team midseason could leave as well: Cameron Maybin, who enjoyed a resurgent season in the outfield, is a free agent, while designated hitter Edwin Encarnación has a $20 million team option for next season, or a $5 million buyout if the Yankees decide to move on.

None of those players is a centrally vital figure for the lineup, though, and the Yankees should boast a formidable offense again next season. They generally have enviable questions to answer, like who plays third base on Opening Day: Andújar, who finished second in Rookie of the Year voting in 2018, or Urshela, who broke out as a Yankee after changing his swing mechanics.

More uncertainty arises in the bullpen. Chapman can opt out from the remaining two years and $30 million on his contract, and Dellin Betances—who, to be fair, faced just two batters this season—won’t return to the mound, because of both free agency and the torn Achilles tendon that ended his season in September. For nearly half a decade now, Yankees GM Brian Cashman has eagerly built a super-pen, but he’ll have to spend to ensure such a strength next season.

The other departing player of note is CC Sabathia, whose retirement after more than a decade in pinstripes opens a rotation spot. The dual returns from injury for Luis Severino and Jordan Montgomery, who combined to throw just 16 late-season innings, could backfill the role easily enough. But after struggling to find a fifth starter for large chunks of the regular season, and then failing to find even a fourth reliable starter for the playoffs, New York would do best to aim bigger this winter.

Their top target should, and likely will, be Houston’s Gerrit Cole, whom the Yankees have coveted for more than a decade. They drafted him 30th overall in 2008, only for the high schooler to attend UCLA instead of signing, and then tried to trade for him before the 2018 season, only for the Pirates to accept Houston’s milquetoast offer instead.

Cole won’t come cheap, nor should he, after setting a single-season record for strikeout percentage before producing a magical—to this point, anyway—postseason run. The Yankees of old wouldn’t bat an eye at Cole’s potential contract; the new, cost-conscious Yankees might. They reportedly didn’t trade for Justin Verlander in 2017 because of his contract, then didn’t match Washington’s offer for Patrick Corbin this winter.

Without Cole, the Yankees could certainly win another 100 games and the division. The roster is that strong at the top, that deep in talent, and they’ll still feast on a schedule filled with Baltimore and Toronto and Detroit, after all. But the Yankees are the Yankees, 27-time World Series champs, and an ALCS visit isn’t enough to sate fans or fulfill the legacy of pinstripes. Just two years ago, suffering elimination at the same stage on the same field, the Yankees were full of promise; now, they’re burdened by an antsy anxiety of when, exactly, the club might return to the World Series, let alone raise another trophy. They can’t truly answer that question until next October, but they can at least start on the work this winter.