Predicting the next 20 Yankees playoff eliminations if Aaron Boone, Brian Cashman stay

The New York Yankees were defeated by the Tampa Bay Rays in a clean three-game sweep in the 2026 ALDS. The Rays were a better team in the regular season and a better team in the postseason. It's a paint-by-numbers elimination for a team that's got plenty of them over the last nine years. Yankees enter the playoffs as a strong regular season team. They lose to a talented team with more nuance. They welcome everybody back next year for another crack at it.

After the loss, Aaron Boone said that his potential return is a "conversation for another day," while both Aaron Judge and Cam Schlittler endorsed a Year 10 of this particular marriage. The man who gave him Trent Grisham, Jazz Chisholm Jr. and Ryan McMahon with which to cook also commented on Boone, endorsing the job he did while kicking any potential conversation about his own performance further down the line.

If both men return ahead of the impending lockout - I suspect they will - then here's how I think the Yankees will be eliminated from the playoffs over the course of the next 20 years.

Predicting 20 more years of playoff failures under Aaron Boone, Brian Cashman

2027: The Baltimore Orioles run roughshod over the AL East in the shortened, 108-game season. The Yankees escape the Wild Card Series after a best-of-three on the road in Cleveland, and ahead of a showdown with the O's, most pundits believe the Yankees' starting pitching advantage and breakout season from Spencer Jones alongside Ben Rice will carry them to victory. The Yankees lose in four after falling down 2-0, defeated 9-1 on their home field. They hit a collective .148 in the series.

2028: After agreeing to a new two-year deal with Boone to stave off a potential bidding war (no rumors of bids were made public), the Yankees lose the ALCS in six games to the new-look Houston Astros, closed out on the road by David Bednar, signed in free agency after the 2026 season so the Yankees could reapportion his money to Shawn Armstrong, Matt Strahm, and Evan Phillips, recreating him in the aggregate.

2029: The Yankees record one singular hit in a four-game Division Series loss to the Seattle Mariners, a walk-off George Lombard Jr. home run in Game 3. After the series, Aaron Boone says he liked the at-bats, noting that the Yankees were this close to really smoking a few.

2030: One year after trading their entire 26-man roster to the Las Vegas A's, the Rays return to the playoffs and defeat the Yankees in five games. Mets fans rejoice en masse on Twitter at the Yankees' elimination after finishing their season at 75-87 with the game's highest payroll by $70 million. After the season, the Yankees flirt with trading for exec David Stearns, but eventually hold firm with Cashman.

2031: The Yankees miss the playoffs, as George Lombard Jr. talks to the media about how much it stings to see grizzled veterans like Anthony Volpe, Ben Rice and Cam Schlittler unable to ever secure the big one (Volpe, by this point, is a three-time All-Star with the Twins, but ... they don't win anything there, either).

2032: Second Lockout after MLB owners throw a fit over the Rays' whole "trading their entire team" thing. No season.

2033: The Yankees emerge from the lockout reborn, defeating Cleveland and Detroit en route to the World Series. Boone pushes all the right buttons. Cashman's midseason masterstroke of dealing for a late-career Bobby Witt Jr. propels the Yankees to new heights. In Game 1 of the World Series in Milwaukee, Boone calls on 41-year-old Ryan Yarbrough to cap his retirement tour and record the final out with the bases loaded, up three runs. Jackson Chourio's walk-off grand slam swings the series, and the Brewers sweep.

2034: The Yankees hold a 16-game lead over the Boston Red Sox until Cam Schlittler sees a hologram of Section 10 host Jared Carrabis hovering outside his porch window. Schlittler posts a photo of the looming hologram on his IG story with the cryptic caption, "Rat boy gonna learn." The Red Sox erase the entire lead in 1.5 months, then somehow flame out worse than the Yankees. Yankees lose the ALCS to the Texas Rangers.

2035: After batting .042 with no home runs and 84 ground ball double plays, Vladimir Guerrero Jr. drills a 442-foot walk-off home run in Game 5 of the ALDS. Mets fans rejoice after finishing 66-96 with the highest payroll in baseball, including a 19-62 record at their home stadium Kalshi Field.

2036: The Yankees lose the ALCS to the Vegas A's on a Game 7 Anthony Volpe walk-off. An addled Cashman wonders why the Yankees can't seem to find players like that. Boone misses a crucial pregame meeting because he's hung up on his inability to come up with a catchy nickname for Yankees star Yostin Pena. Pena-y?

2037: A four-game ALDS loss in Cleveland leaves Yankees rookie Greg Torta lost for words. "You've got veteran guys like George Lombard Jr. and Spencer Jones who've been at this forever, and they don't have a ring to show for it," Torta tells the media. "It just really hurts. This is a broken clubhouse."

2038: A heartwarming moment at Yankees Old-Timers' Day, as Giancarlo Stanton addresses the current roster with a rousing message of, "We don't get swept at home!" hours before the San Francisco Giants finish off the sweep. The Yankees lose the ALCS in five to the Chicago White Sox.

2039: The Yankees miss the playoffs; the Boston Red Sox celebrate Cam Schlittler's farewell tour by presenting him with Jared Carrabis' Twitter password.

2040: The Yankees lose the ALCS in six games to the Mariners. Boone accidentally begins his post-loss press conference eating a big ham sandwich.

2041: Cashman's shrewd deadline trade of the Yankees' top four prospects for Frankie Montas Jr. pays off; the Yankees surge in the second half and only miss the playoffs by four games, nearly securing MLB's brand new fifth Wild Card.

2042: The Yankees, on the precipice of the FanDuel World Series, turn a tailor-made double play into a two-run fielder's choice on a Ryan McMahon Jr. overthrow; the Astros win the series in six. Mets fans have convulsions laughing while sharing the clip, then go back to mourning their franchise folding in 2040, sold to Dubai businessmen and folded in order to re-finance debt from a new kind of chocolate they invented (with nicotine).

2043: For the first time in 10 years, Aaron Judge returns to Yankee Stadium for Game 5 of the ALDS. Instead of sitting with Cashman in the suite, he chills next to Lorne Michaels and Jimmy Fallon. Junior Caminero, acquired from the Rays after the 2040 season (he's bad now), strikes out looking for the final out.

2044: Third Lockout after FanDuel's sponsorship of the World Series goes belly-up. No season. In a mid-October press conference, Boone assures fans this would've been the year, but, you know ... lockout and all that.

2045: The Yankees lose the ALCS in five games to the Minnesota Twins. The final out of Game 5 is, somehow, Giancarlo Stanton swinging over a late-breaking slider in the other batter's box.

2046: The Yankees win the World Series for the first time in 37 years on a dramatic Game 7 home by Greg Torta that sends the Bronx into an absolute frenzy. Two hours later, after the confetti has fallen and the champagne has dried, the home run is overturned by a late replay review; Torta's bat is shown to have an illegal amount of pinetar. The game is replayed the next day and the Yankees lose in 11. 73-year-old Boone and 79-year-old Cashman both receive three-year extensions for getting so close.

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