Skipper Aaron Boone’s contract ends after the 2027 season, and the New York Yankees have not won a World Series since he took over. They have not won one since 2009, long before Boone joined. Captain Aaron Judge actively spoke about “unfinished business” but has himself landed on the IL. The playoffs are less than a week away, and according to an MLB insider, this is high time Boone steps up and gets the job done.

“Whether he [Aaron Boone] is or he isn’t [getting fired], he should manage like his job’s on the line and really go with his baseball gut,” said Joel Sherman of the New York Post.

“If he thinks that Anthony Volpe gives him the best chance to win, play him. If he thinks Jazz Chisholm gives him the best chance to win, play him. Play who you think gives you the best chance to win … this has to be utter ruthlessness.”

Last season, the Yankees were tied with the Blue Jays for the top spot in the AL East. The Blue Jays won the division title, and the Yankees beat the Boston Red Sox in the Wild Card Series to advance further.

But the Blue Jays cut their playoff run short by defeating them in the ALDS.

This season, the Yankees have secured a postseason berth, but they trail the Tampa Bay Rays by 6 games. With Aaron Judge on the IL due to a calf strain, the chances of winning the AL East title are slim. They needed to sweep the Rays, but instead lost Game 2 of the doubleheader 6-1 to Tampa.

As the Yankees prepare to play the Wild Card contest against their nemesis, the Boston Red Sox, New York does not want a repeat of last postseason.

Sherman’s strategic advice stemmed from the pattern as he pointed out:

“There is a team almost every year who just outplays them in the A.L. East and wins the division. They get in, but somebody outplays them almost always. And that team last year eliminated them in the division series. You gotta win in the playoffs this year.”

To achieve that, Aaron Boone must strictly take control of the team, per Sherman.

The skipper must select the players he believes will take the Yankees deeper into the postseason.

Before the day-night doubleheader against the Rays on Tuesday, the Yankees activated Jazz Chisholm Jr. from the injured list. He landed on the 10-day list with a sprained right thumb. He went 1-for-3 and drew a walk against the Rays.

Boone has now led the Yankees to eight playoff appearances in his first nine years of coaching. In recent memory, 2024 was the most successful season for the Yankees.

They won the AL Pennant and advanced to the World Series, even though they ultimately lost the Fall Classic to the Dodgers.

The Yankees need Boone to pursue the World Series ring more than ever, with Judge on the IL. He needs to hype his players up so that the captain’s absence does not affect the team’s spirit.

Following his return to the lineup after missing 84 games due to a stress fracture in his ribs, Judge is back on the 10-day IL. This time, due to a calf strain that he thinks dates back to Spring Training.

Speaking about Judge’s calf strain, Sherman reportedly said, “Calf strains are notorious for when they heal. Let them heal more because it is a re-injury area of the body.”

Judge will miss the rest of the regular season. But according to recent reports, the Yankees captain will not be playing in the Wild Card Games either.

He has reportedly taken a plasma injection in his legs on Monday.

If the Yankees advance past the Wild Card games, Judge will hopefully be ready to hit in the ALDS. But first, Boone has to keep his team going.