In the world of professional sports, there’s a specific type of purgatory reserved for coaches who always win but never win it all. For the NFL, it’s Mike Tomlin. For the New York Yankees, it’s Aaron Boone. Now, he’s facing mounting criticism for the team’s inability to perform when it matters most.

Legendary sportswriter Neil Best explains the matter with Brian McKeon and Stacy Gotsulias of the Locked on Yankees podcast, as the hosts ask him about Boone’s decade-long managerial journey with the Yankees.

“I guess [Aaron Boone]’s a lot like Mike Tomlin because he always wins, but he doesn’t win the big one. The guy wins; he has more resources than most managers, but it really, really would help to win a championship. But I guess it is similar to Tomlin. Like they never have a losing record, just like Tomlin never had a losing record. And in that sense, Boone has been very successful, but you’re supposed to win a championship,” Best reflected on Boone’s managerial style.

The comparison to former NFL coach of the Pittsburgh Steelers, Tomlin, is apt; both coaches consistently avoid losing seasons.

Tomlin had a 193-114-2 regular season record and an 8-12 postseason record over 19 years of his NFL career. He won Super Bowl XLIII in 2008. But since then, he had failed to win the championship trophy. And Aaron Boone?

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He has a 697-497 record in the league so far and has led the Yankees to seven postseasons with one World Series appearance (2024).

Compared to the New York Mets, the Yankees have more financial resources. The team’s valuation stands at $8.2 billion along with a revenue of $728 million, according to Forbes. Despite that, Boone and the Yankees have failed to win a World Series, just like Tomlin failed to win the playoffs since 2016.

Last season, it all started with the team failing to properly address their third base needs.

They used players like a recovering DJ LeMahieu, Oswaldo Cabrera, and Oswald Peraza. Additionally, the team struggled with pitchers like Carlos Rodon and Clarke Schmidt suffering injuries. Plus, poor performances from players like Jasson Dominguez and Devin Williams ended the team’s postseason dreams at the hands of the Toronto Blue Jays in the ALDS.

But Neil Best didn’t just criticize Aaron Boone for his World Series failures, but also for his personality when addressing the media.

“As far as with the media, which again is what I care more about, a lot of the beat writers get a little tired of his answers sometimes, and he’s too positive.”

Aaron Boone’s overtly positive mindset for a struggling Yankees team has even frustrated fans.

After their Game 2 loss in the Subway Series, all Boone could say was, “It was a really great baseball game. It really was.”

And it looks like Boone has taken the optimism to believing in almost the same roster.

Their pitchers like Gerrit Cole, Carlos Rodon, and Clarke Schmidt are expected to rejoin the team. However, since all three are returning from injuries, they may not be at their 100%. Likewise, their new pitcher, Ryan Weathers, cannot be expected to carry the team due to his injury-prone nature.

Among the hitters, Jasson Dominguez struggled last season and cannot be guaranteed to rebound and improve his performance this season.

Now, considering all these factors, the Yankees might find their World Series dreams ending once again this season.

Even then, Boone had continued to disagree with the critics about his team members and their importance for the upcoming season, especially Anthony Volpe.

Aaron Boone displays reliance on Anthony Volpe for this season

The 24-year-old shortstop is returning after suffering from a partially torn labrum in his left shoulder. And Aaron Boone has shown his full confidence in Anthony Volpe.

“I still think Anthony’s gonna be a frontline shortstop in this league. Everyone’s path isn’t linear. We always want it to be, and that can be tough, especially in New York, where you’re kind of finding your way,” Boone stated.

Anthony Volpe struggled throughout last season, especially during a 10-game stretch from August 15, 2025, to August 26, 2025, recording 33 plate appearances with only 1 hit and no walks. He also had an on-base percentage of .031 during that phase, considered the worst in Yankee history.

Despite his struggles, flashes of Volpe’s potential were evident, like his Opening Day solo home run off a 95.4 mph fastball from Freddy Peralta, a blast of 103.8 mph exit velocity that showcased his raw power. In 153 games, he recorded 19 home runs and 72 RBIs.

Now, Anthony Volpe will resume his role as the Yankees’ shortstop with the infield mix of Amed Rosario, Oswaldo Cabrera, and Jose Caballero.

The upcoming season will be the ultimate test: can Boone’s faith in players like Volpe finally end the Yankees’ championship drought, or will it just extend to another year!