New York Yankees manager Aaron Boone speaks during a baseball news conference, Thursday, Oct. 16, 2025, in New York. (AP Photo/Ronald Blum)

Associated Press

From 1998 to 2000 it seemed as if all the Yankees needed to do was snap their fingers, get a big hit, a big out on the mound and win the World Series as evidenced by going 12-1 in World Series games and winning 10 of those games by three runs or less

Those days are long gone due to a combination of things, an expanded playoffs making the path to 11 or 13 victories more challenging or a lack of execution in the biggest spots of a season.

The theme from the Yankees during the 68 minutes Aaron Boone and Brian Cashman spoke on Thursday as the Blue Jays and Mariners prepared for Game 4 of the ALCS, highlighted the theme defining most of the past 16 seasons about being in the mix or one of the best teams in baseball.

Since winning their last World Series title in 2009, the Yankees are 42-47 in 89 postseason games. The only five occurring in the World Series occurred last season against the Los Angeles Dodgers when the Yankees lost Game 1 on a game-ending grand slam by Freddie Freeman and Game 5 at home by flushing a five-run lead.

In sixteen different seasons, the Yankees held some kind of postmortem press conference inside a quiet Yankee Stadium and each one touched upon laments about how a postseason or in the case of 2013, 2014, 2016 and 2023 a season went awry.

The latest reiterated faith in how the Yankees reach the postseason like the way they spoke last season after their season went to Oct. 30. Unlike last season when the ability to retain Juan Soto was a big topic, free agency was not a huge talking point other than the generalities spoken about Cody Bellinger, who will opt-out and was a move that worked out perhaps even better than envisioned due to his production and versatility in the outfield.

“The reality is we’ve had a really good club — in certain years, probably one of the best clubs in the league,” Boone said. “But all I know is that it’s time to dust ourselves off and try to build another club that puts us in position to take a run again.

“I can’t answer that because I haven’t got this team to the top of the mountain. Until I do, all I can tell you is I’m confident in my ability to lead this team. I’m confident in our organization to build a team that gives us a chance to win. But ultimately, I can’t tell you anything to make you feel good.”

This season, the Yankees shared the best record in the AL with the Toronto Blue Jays. The separator was some of their eight losses to them, which cost the Yankees the tiebreaker and homefield advantage.

“It is tough,” Cashman said. “It is really difficult to do and it’s easier to talk through or what have you, but actually for those guys in the competition, it’s obviously something that we aspire to do once again and in some cases aspire to do for the first time.

“So whether it’s controlling your emotions, whether it’s being at your best at the most important time on any given at-bat, any given pitch and stringing that all together, that is what we continue to fight for and try to find our way through it, and then trying to walk and talk through it after the fact is something we’d like to avoid.”

Last season, the Yankees finished the best record in the AL, beating Cleveland by 1 1/2 games but their flaws and imperfections appeared against the Dodgers, especially in the series clincher.

Three years ago, when Aaron Judge hit 62 homers and his free agency was on the mind of many, the Yankees finished with 99 games, good enough to win the division by seven games but also seven behind the Astros. The Yankees also ended with a banged up lineup, resulting in them hitting .182 in eking past Cleveland in the Division Series and .162 in a four-game sweep by the Astros in the ALCS.

This year the Yankees were mostly healthy on the surface. With Gerrit Cole recovering from Tommy John surgery on his right elbow, Max Fried and Carlos Rodon combined for 37 wins, nearly 400 innings and 386 strikeouts but both struggled in the Division Series against the Blue Jays.

While the Yankees won the game pitched by Rodon, there might be a cause for his diminished velocity and struggles in the postseason. Early in Thursday’s press conference, Boone revealed Rodon underwent a scope of his left elbow and the purpose was to remove some loose bodies and shave down a bone spur.

“I don’t know what that means to where we put our remaining resources and how we reinforce,” Cashman said. “Do we have enough from within? Do we have to go outside to augment? You can never have enough pitching. So, I don’t know. The good thing is he’s coming back. I have to make sure there’s room on the roster when he does.”

The other health concern to emerge on the 22nd anniversary of Boone’s homer to win the 2003 ALCS (though the homer occurred at 12:16 AM on Oct. 17) pertained to Anthony Volpe undergoing surgery for a partially torn labrum on his left shoulder.

While the Yankees hedged about him needing surgery when they announced the shortstop had the labrum tear on Sept. 11, it seemed to be something headed for a procedure.

There were mixed messages on Volpe’s status and whether the injury impacted him hitting .212 and 1-for-15 with 11 strikeouts in the ALDS.

Other than the one team who wins the World Series, 29 other teams will hold some variation for these. For 16 straight seasons, the Yankee version is providing updates on injuries and lamentations of how they fell short while hoping to avoid the raw emotional pain of losing in the playoffs.

“It’s hard to win the World Series,” Boone said. “Been chasing it all my life,”

In the meantime, the first part of the chase to avoid a 17th straight post-mortem press conference without a title starts with various meetings to plan for offseason moves.