The longest current partnership between a GM/head of baseball operations and manager in baseball is the one between Andrew Friedman and Dave Roberts with the Dodgers. Since they got together in 2016, Los Angeles has won nine National League West titles in 10 years, won the World Series three times and lost two others in 2017-18.
The next longest is the partnership between Mike Hazen and Torey Lovullo in Arizona, together since ’17. They have been to the playoffs twice and the World Series once.
Then there is the partnership -- and it’s a strong partnership -- between Brian Cashman and Aaron Boone with the Yankees. Cashman decided to move on from Joe Girardi even after he had taken New York to Game 7 of the 2017 American League Championship Series against the Astros. In eight seasons under Boone, the Yankees have won the AL East title three times and made it to the ALCS three times, finally making the World Series in 2024 for the first time since ’09, the last time they won it all.
Now the Cashman/Boone Yankees will try to make sure they don’t go 17 straight seasons without winning the World Series, which would tie the franchise's longest championship drought since Babe Ruth came to the Bronx -- and the Yankees truly became the Yankees -- more than 100 years ago.
There is pressure on the Yankees to turn back into The Yankees every year, even with a string of consecutive winning seasons that goes back to the middle of the 1990s. And this season is no different.
Here is something Aaron Boone said about all of this the other day:
"[Not winning the World Series] bothers me a lot. It's definitely as big a motivator and what drives me to still do this as much as anything ... that chase to ultimately get No. 28 is as big a reason as any, and it does bother me."
It is clear with the moves the Yankees have made -- and the ones they haven’t made -- since losing to the Blue Jays in four games in the 2025 AL Division Series that they are essentially “running it back” with last year’s team, a phrase used so frequently these days in New York that you keep waiting for it to show up on T-shirts.
The Yankees improved their bullpen at the Trade Deadline last year, most notably with closer David Bednar. They are getting former ace Gerrit Cole back from Tommy John surgery eventually, along with Carlos Rodón, also at some point this season. New York re-signed Cody Bellinger, the second-most valuable member of the team last season after Aaron Judge, to a five-year deal.
Cashman, who has pushed back on the notion of the Yankees totally running it back, has said this:
“I've been openly willing to challenge anybody that [says] we don't have a championship-caliber roster and team.”
Now he will see and Boone will see, and Yankees fans will see about that. Of course, New York won 94 regular-season games last season, tied with Toronto for the most in the American League. Across Boone’s eight seasons, he has won more games than any current manager other than Roberts.
But despite all those wins last season, the Yankees did struggle against teams that ultimately made the playoffs. They were 28-34 against those teams in the regular season and had a 5-8 record against the Blue Jays, which cost New York the AL East title by virtue of losing the tiebreaker. When you add in their ALDS loss to Toronto, they were 6-11 against Toronto overall.
And there is one other troubling statistic for the Cashman/Boone Yankees in recent seasons, despite all the winning their teams have done. In their last three closeout postseason series -- against the Astros in the ’22 ALCS, the ’24 World Series against the Dodgers and against the Blue Jays last October -- their record is 2-11.
The Yankees have been really good since Cashman selected Boone to replace Girardi, they've been a model of consistency, and they have consistently given themselves a chance by making the playoffs. They have not played well enough when the season is on the line.
Cashman clearly believes this is the team with which he wants to make his run, and once again the manager with whom he wants to make that run. Both Cashman and Boone say that they have a “championship-caliber” roster.
Starting with their Opening Day game, in San Francisco on March 25, we’re all about to find out. The number they want is No. 28, for another World Series. They don’t want No. 17, another year without one.