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Diary of a Yankees Fan #5: Needed Leadership Changes

ESPN's Jessica Mendoza chats with Bryce Harper on Gatorade All-Star Workout Day. Diary, she would be a good managerial hire for the Yankees.
Credit: Arturo Pardavila III from Hoboken, NJ, USA

Dear Diary, one of the most vexing problems with the Yankees over the past 9 years has been their manager. He makes strange decisions, then defends them. Another problem with the team is the General Manager. Crian Cashman has ossified in that role, and this season’s trade deadline shows he has lost a step. Both of the people will likely be back in the positions for the 2027 season, but that does not mean we should not explore options.

The results on the field dictate whether Aaron Boone and Brian Cashman should be back with the Yankees. Unfortunately for them, the Yankees were embarrassed at home by the Tampa Bay Rays, who swept them in the Division Series, and then celebrated at Yankee Stadium. The 17 years the team has gone without winning a World Series is a franchise high, and this most recent trade deadline did not yield what the team needed. Diary, are both Boone and Cashman done?

Diary of a Yankees Fan

Boston Red Sox manager Alex Cora, would be an excellent General Manager for the Yankees. Diary, do you think? Mandatory Credit: Mitch Stringer-Imagin Images
Apr 24, 2026; Baltimore, Maryland, USA; Boston Red Sox manager Alex Cora (13) before the game against the Baltimore Orioles at Oriole Park at Camden Yards. Mandatory Credit: Mitch Stringer-Imagin Images

The Yankees cannot fire their players after having a disasterous end to their season. They need a leadership change. This will not happen; however, the results on the field dictate that both Aaron Boone and Brian Cashman must be replaced. Who are the leading candidates? Some will be listed in this diary.

Manager

Jessica Medoza is the first managerial candidate for the Yankees. Diary, we realize a woman has never managed a baseball team, but there is no reason one could not do it. In fact, a team might be better off with the even-handed approach of a woman. This may seem like an odd choice; however, there is precedent for someone with no managerial experience to come out of the television booth at ESPN.

Rocco Baldelli would be another candidate. The Minnesota Twins fired him, but he was fairly successful in his time in Minnesota. he did a pretty good job during his seven seasons with the franchise. He led the team to three division titles, including just the second 100-plus-win season (2019) in team history. That’s impressive for a franchise that is a borderline small-market club based on how they spend.

Albert Pujols could be another candidate to manage the Yankees, diary. He has long wanted a managerial job, and as one of the best right-handed hitters in Major League Baseball history, he deserves one. In March, he offered an example of his capability as a manager when he guided a star-studded Dominican Republic squad to the World Baseball Classic semifinals. This demonstrated that he can handle a talent-rich roster with big personalities and paychecks, just like the Yankees.

There are some other interesting candidates to manage the Yankees. They would not have to look far for current Bench Coach Brad Ausmus. The former manager of the Chicago Cubs, David Ross, could be another. How about George Lombard Sr.? He is qualified in his own right and would make a powerful father-son combination. If the Phillies move on from Don Mattingly, he could be a fan-friendly alternative. Hall of Famer Carlos Beltran could be another.

General Manager

Some qualified candidates could replace General Manager Brian Cashman, diary. The top candidate, and crowd favorite, Derek Jeter. The former Yankee captain has some leadership experience after his Hall of Fame career. Another candidate with experience would be Theo Epstein. What about Sean Casey or Kevin Reese? Reese is currently in charge of player development for the Yankees. Another idea would be Brian Saban, who was the General Manager of the San Francisco Giants from 2009 through 2015.

Conclusion

The Yankees need to make changes to their leadership. They have had failure after failure on the field. They will not make a change, as managing general partner Hal Steinbrenner has proven he is risk-averse, and definitely not his father. He is both reluctant to spend money and he is reluctant to make leadership changes. In fact, many think he protects both Boone and Cashman. Boone is under contract through the 2027 season; it will be interesting to see if the team goes in a different direction then, perhaps one suggested in this diary.

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