“New York Yankees: The Aftermath” is a three-part series with my suggestions on how the Yankees should proceed with their leadership (part one), players (part two), and roster construction (part three).
OWNERSHIP
The long shadow of George Steinbrenner continues to loom over the franchise. Folks of a certain age remember the swashbuckling days in the 1970s when he was wining and dining Reggie Jackson and hiring and firing Billy Martin.
Younger fans remember him as an older, mellower Boss shedding tears with Joe Torre while holding World Championship trophies in the New York Yankees locker room. No one talks about the nine-year stretch from 1982 through 1990 when they missed playoffs every year. A streak that continued until 1995.
- 1982 (Bob Lemon, Gene Michael, Clyde King)
- 1983 (Billy Martin)
- 1984 (Yogi Berra)
- 1985 (Yogi Berra, Billy Martin)
- 1986 (Lou Piniella)
- 1987 (Lou Piniella)
- 1988 (Billy Martin, Lou Piniella)
- 1989 (Dallas Green, Bucky Dent)
- 1990 (Bucky Dent, Stump Merrill).
Ah, the good old days. Now, in fairness, under today’s expanded playoff format, with six teams qualifying in each league, the Yankees would’ve had some success. But what is forgotten is the toxic way George ran the franchise in that era.
He ridiculed his beloved captain Don Mattingly on a few occasions. Once for having his hair a tad too long, and another for hitting home runs in eight consecutive games. He blamed that streak for a subsequent sprained wrist and said that Mattingly’s streak was a distraction.
Of course, he was also permanently barred from baseball in 1990 for conspiring against his Hall of Fame outfielder Dave Winfield. That suspension, lifted in 1993, enabled GM Gene Michael and manager Buck Showalter to build the core of the 1996-2000 dynasty.
In 2026, The Boss is a mythical figure. His legacy has been reimagined, and the result is that undue pressure is applied to his son Hal.
Aaron Judge said after the Yankees season ended, “We’re the Yankees, I feel like they should go all in and do what they need to do and find. If we’ve got holes, if it’s finding certain players or personnel, whatever we need, you’ve got to go out there and get it”.
With all due respect to the captain, what does he think the Yankees have been doing over the last few offseasons?
- Prior to 2023 season, retained Judge with a 9-year/$360m contract and signed Carlos Rodon to a 6-year/$162m deal.
- Prior to 2024, traded for Juan Soto.
- Prior to 2025, offered Soto $760m and then pivoted to sign Max Fried for 8-years/$218m, and acquired Cody Bellinger and Devin Williams via trades.
- Prior to 2026, retained Cody Bellinger with a 5-year/$162.5m contract and acquired Ryan Weathers.
The Yankees luxury tax payroll was ranked in the Top 3 all four seasons including in 2026 when they placed third behind the Los Angeles Dodgers and New York Mets. I’m going to go out on a limb. The fanbase may not be proud of Hal Steinbrenner, but I’m guessing George is.
BRIAN CASHMAN
Brian Cashman is not nearly as stubborn as his detractors say.
In 2022 we killed him because his 99-win team got swept in the ALCS by the 107-win Houston Astros. We told him his team was too right-handed and didn’t possess enough athleticism.
This year’s team featured eight left-handed hitters and two players who finished Top 5 in stolen bases in the American League — Jazz Chisholm (41) and Jose Caballero (34).
We’ve killed him for not staying on top of trends. But after witnessing starting pitching carrying the Los Angeles Dodgers to back-to-back World Championships, he built the most effective rotation in 2026 featuring Cam Schlittler, Max Fried, Gerit Cole, Carlos Rodon, Will Warren, and Ryan Weathers.
We’ve killed him for an underperforming development department. Meanwhile, the system has developed three-time MVP Aaron Judge, soon-to-be Cy Young Award winner Cam Schlittler, All-Star Ben Rice and eight other players who contributed in 2026 including Spencer Jones, George Lombard Jr, Anthony Volpe, Will Warren, and Austin Wells.
We’ve killed him for being a product of his payroll. Meanwhile, we’ve watched the New York Mets outspend him the last two years and not sniff the playoffs.
My Real Take is that Cashman deserves a plaque in Monument Park and a bust in Cooperstown upon his retirement. While that is not a popular opinion, it’s based on facts. In 29 years on the job he’s made the playoffs 24 times, reached the World Series 7 times, and has won 4 World Championships.
Most impressively, he’s never overseen a team with a losing record. That should slap some cold water on the “game has passed him by” narrative.
AARON BOONE
Aaron Boone has been the manager of the Bronx Bomber for 9 seasons, making the playoffs 8 times, and compiling a 790-565 regular season record. That equates to a .583 winning percentage which places him 10th all-time among those who have managed a minimum of 1000 MLB games.
The biggest criticism of Boone is that he sticks up for his players as if that’s a bad thing. The days of Billy Martin pulling Reggie Jackson out of right field in the middle of an inning are long gone. In today’s society, across most businesses, leadership must come from a position of respect.
Boone is also criticized for being positive with the media when things are going poorly for his team. This is not a bad thing. Boone is not only the field boss, but he’s also the spokesman for the Yankees every day during the season. In my opinion, being even-keeled and positive is a sign of a good leader.
Finally, Boone has been criticized for his inability to beat teams with better regular season records in the playoffs. Conceptually, I understand the frustration in the Yanks inability to pull off an upset, but he’s consistently beaten the teams he was supposed to beat. That’s a good thing.
Again, it’s a new era. Boone passionately defends his players, continuously praises the fans, and shows incredible patience with the media. In many ways, he is the epitome of the moder manager.
MYSTIQUE AND AURA
Outside of the Bronx, a 17-year title drought might not seem like such a big deal considering five MLB teams, 10 NBA teams, 10 NHL teams, and 12 NFL teams have yet to hold the Commissioner’s Trophy, the Larry O’Brien Championship Trophy, the Stanley Cup, or the Vince Lombardi Trophy.
That doesn’t mean I feel bad for Hal Steinbrenner, Brian Cashman, or Aaron Boone. The Boss started the “title or bust” mentality, so they are simply dealing with The Aftermath of the rhetoric that the organization created.
“Mystique” and “Aura” may not show up at the current stadium as much as they did at the old one across the street. But the Yankees still enter each season among the favorites to return to the World Series — and they still are playing ball most Octobers.
The leadership team has work to do, and they need to be open to continued philosophy changes, but they’ve earned the right to continue the quest for #28.
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