Yankees finalize Aaron Boone contract extension and confirm World Series timeline

It has arrived, New York Yankees fans. Aaron Boone's contract extension — something that's been referred to as a fait accompli — is official. He will be guaranteed to remain in the Bronx beyond the 2025 season.

But if we're to read the tea leaves here, it's apparent the Yankees might have drawn a line in the sand with Boone's tenure. Years ago, Brian Cashman said he'd like if Boone managed the Yankees for 10 years, much like his predecessors Joe Girardi and Joe Torre.

Boone's extension is a two-year deal that takes him through the 2027 campaign. If he finishes it out, that will be ... 10 years at the helm. And it couldn't be more in line with this team's World Series window based on the contracts they have on the books.

Chances are, Boone will not head into the 2027 as a lame-duck candidate, much like how he didn't after the Yankees exercised his previous options and then avoided that drama this offseason with an extension.

It's either Boone guides this team to a championship by 2026 and either gets another short-term extension or retires, or there will be a mutual parting of the ways after the 2026 campaign. It kind of feels like there's no in between, but that's just us trying to read the situation a bit deeper.

Yankees News: Aaron Boone's contract extension finalized before 2025 season

Many have questioned Boone's abilities in big moments and October. Yes, he has some moments of success, but fans are more apt to remember the failures, especially if they outweigh the successes, which has been the case with Boone since he took over in 2018.

That year, he got romped by the hated Red Sox in the playoffs. The next year featured one of the most heartbreaking series in recent memory in the Yankees' ALCS rematch against the Astros. The 2020 season? Disaster + JA Happ in the ALDS. The 2021 campaign was another disaster that was ended by Boston. In 2022, they were once again out-classed by the Astros in an ALCS sweep. They missed the playoffs in 2023 in what was the worst season in 30 years. Then, some might argue Boone ruined the team's World Series chances after his pitching decisions in Game 1, followed by the team unraveling defensively to put the final nail in the coffin.

Boone's winning percentage (.584) ranks eighth in Yankees history, but it feels like that's mostly been achieved on autopilot. Whether it's Aaron Judge winning MVPs or the team getting fueled by unlikely sources such as DJ LeMahieu (2019-2020), Gio Urshela (2019-2020), Matt Carpenter (2022), and others, the Yankees have benefitted from excess talent during his tenure while failing to maximize other sources on the roster.

The unfortunate reality is that one unimpressive World Series appearance in seven years doesn't cut it in New York. Perhaps that changes the next couple years, but Boone's extension might actually put an expiration date on his time in the Bronx.