Brian Cashman: On The Mysterious Overhype Behind A 22-Year GM Run

Brian Cashman holding on for dear life as the Yankees 2023 season unfolded

Brian Cashman, if nothing else, has proven that survival is the better half of success. Overhyped, the reality is quickly catching up with facts.

Brian Cashman has been the Yankees’ General Manager since 1998 when he assumed the position from Bob Watson as an appointee of George Steinbrenner.

Going on 22 years, Brian Cashman will surpass Ed Barrow, the longest-tenured GM in Yankees history this season.

Brian Cashman, Yankees Stealth Bomber (Photo Credit: Greedy Pinstripes)
Brian Cashman, Yankees Stealth Bomber (Photo Credit: Greedy Pinstripes)

With four World Championships earned during his ride, Cashman, if he worked for any team, but the Yankees and their annual World Series title or bust mantra would be a unanimous lock for election to Baseball’s Hall Of Fame.

But these are the New York Yankees, who by their self-defined measure of a season’s success or failure are mired in a twelve-year drought, still in search of that elusive 28th World Series title since 2009.

In a sport where awards are typically given to winners, Brian Cashman was named as Baseball America’s 2017 Major League Executive of the Year – not for winning a title but for “finishing one victory shy of advancing to the World Series.” (

Brian Cashman: Cashing In On A Title That Wasn’t His

How lucky can a man get? Similarly, The Boston chapter of the Baseball Writers’ Association of America selected Cashman as their MLB Executive of the Year for 2009.

This, despite the fact it was George Steinbrenner who executed a writ demanding the Yankees sign the top three free-agents that season, CC Sabathia, A.J. Burnett, and Mark Teixeira.

With Steinbrenner’s checkbook to back him, Cashman dutifully signed all three, and the opening of the new Yankee Stadium was adorned with the Boss’s wishes – another flag hoisted above the facade.

However, operating on his own and with the death of George Steinbrenner in 2010, success has proven more elusive than most people realize in areas away from the spotlight of trades and free-agent signings.

Most significant of these is the measure of success Brian Cashman has had in the annual MLB June College Draft. Time out while we peruse the record of Cashman since 2009.

Justus Sheffield, New York Yankees Photo Credit: New York Sports Day
Justus Sheffield, New York Yankees Photo Credit: New York Sports Day

Familiar names will pop at you, but every one of them is no longer connected to the Yankees, having failed to progress in their farm system, or more likely, traded away as bait for a lightning in a bottle solution to a problem Brian Cashman was facing.

Adam Warren, Tyler Austin, Dante Bichette, Jr, Greg Bird, Jack Cave, Nestor Cortes, James Kaprielian, and Blake Rutherford were all drafted during the Cashman regime as highly touted “proof” the Yankees’ farm system was in good hands.

Like Michael Pineda, others fell into a “we give up” slot with the Yankees, only to be traded away to fulfill his potential with another team (13-5 with the Minnesota Twins 2019-20).

Count Justus Sheffield (4-3, 3.58) in the same mold, too, as a player Cashman obtained in a trade with the Cleveland Indians for Andrew Miller, only to pre-emptively dump him in a trade last season with the Seattle Mariners for oft-injured James Paxton.

Brian Cashman: What Have You Done For Us Lately

For anyone who has had the same job for more than two decades, as the case is with Brian Cashman and me, typically there is a parabolic curve that defines our performance and level of interest over time.

What Goes Up Must Come Down
What Goes Up Must Come Down

Guided by youthful enthusiasm and the drive for success, we do our best work in the middle years, and then there is a gradual decline until, eventually, we retire or seek new employment.

We can see the same thing in most ballplayers’ careers whose “prime” years are between the ages of 28-32, and it’s the same reason why teams are refraining from multi-year contracts except for the most elite player like Gerrit Cole.

From The Outside Looking In The Fishbowl

From the outside looking in the fishbowl, all I can do is ask the question – Has Brian Cashman peaked, and is his best work behind him?

Theo Epstein voluntarily resign as the Cubs GM
Theo Epstein voluntarily resigns as the Cubs GM.

And if that’s the case, is there any thought being given by Hal Steinbrenner to “retiring” Cashman with a move upstairs, perhaps with a new title as Vice-President Of Baseball Operations?

Recently, Theo Epstein, for instance, voluntarily resigned as the GM of the Chicago Cubs.

Having achieved enormous initial success in delivering the first World Title in a gazillion years to Cubs fans, the dynasty he and others had hoped for never materialized.

Ironically, Epstein had the same experience during his tenure with the Boston Red Sox – initial wild success followed by a rapid decline, propelling his move to Chicago.

Look, this is not to say that Brian Cashman is failing. But sometimes, there is a benefit of change for the sake of change, as we see with managers in baseball all the time.

Was Joe Girardi, for instance, run out of town by the Yankees due to “bad managing”? No, in fact, the Yankees have never given the concrete reason(s) why he was let go.

And that’s because there were no reasons, except to say the Yankees wanted to “move in a different direction” with Aaron Boone.

The Yankees Are Predictably Boring

The Yankees are a staid organization. There is little or no excitement in a fan base that can’t afford to take their family to a game at Yankee Stadium without banging a credit card to the tune of $300-500 for an evening of entertainment.

The team regularly makes the playoffs, but ho-hum, that is merely what is expected.

Buying a ticket today for a game on August 14 is like playing Russian Roulette if your main interest is for your son or daughter to see their favorite players, Aaron Judge and Giancarlo Stanton, in the lineup that night.

Brian Cashman: Past Your Prime So Pass The Baton

It was Satchel Paige who once said, “Don’t look behind you cause someone may be gaining on you.” Said in jest, of course, the Yankees are “this close” to becoming the other team in town as Steve Cohen sets out to light a fire under the Mets fan base.

Mets: Let the good times roll (Photo: AP/New York Post composite)
Mets: Let the good times roll (Photo: AP/New York Post composite)

Even more significant is the multitude of baseball fans who go with the day’s winner, especially towards the end of the regular season.

There will always be Diehard Yankees Fans who see the glass half-full, and perhaps Steinbrenner, Brian Cashman, and the shareholders are content to play to the chorus that triumphantly shouts, “Hey, we came within one out of the World Series against those cheatin’ Astros.”

But I submit the Yankees are stuck in a quagmire of indecision and revving engines going nowhere, and it is Brian Cashman who pulls the puppeteer strings that are all but worn out.

Brian Cashman, you did well, and thank you for your service. But the gig is up, and it’s time to pass the baton.


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Author: stevecontursi

I am an amateur writer with a passion for baseball and all things Yankees and Mets.