Brian Cashman: Revisiting The Legacy Of The Yankees Longest Lasting GM

Brian Cashman, GM, New York Yankees Photo Credit: NBC Sports

Brian Cashman has long been considered one of the elite GM’s in MLB. But on closer inspection of his record, all that glitters is not gold.

Brian Cashman has had a good ride as the General Manager of the New York Yankees since 1998. He is replacing Ed Barrow, who served for 23 years as the longest-tenured GM in the Yankee’s history.

Brian Cashman: Decisions in unknown territory
Brian Cashman: Decisions in unknown territory

Along the way, Brian Cashman has established a reputation as a savvy trade partner and a willing complement to the Yankees managing partner’s wishes, Hal Steinbrenner.

He was selected MLB Executive of the Year for 2009 by the Boston chapter of the Baseball Writers’ Association of America, which notably was the last year the Yankees claimed a World Series title.

But if truth be told, Brian Cashman’s reputation has been fortified more as the benefactor of good luck and circumstances than through his own efforts and contributions to the Yankees over the years.

Brian Cashman: A Muted But Accurate Revisionist History

History, generally, goes through several revisions as time passes. What we once believed or knew to be “true” is supplanted by new sets of facts and theories.

This is offered as a perspective on Brian Cashman’s tenure, and as you will see, all that glitters has not necessarily been gold.

Brian Cashman: A Rookie GM Is Welcomed With Gifts

The Yankees won the first of three consecutive World Championships in Brian Cashman’s rookie season in 1998. The run was highlighted by the Yankees winning every World Series game played except for one. (1998 Padres 4-0), 1999 Braves 4-0, and 2000 Mets 4-1)

Gene Michael, Architect of the Yankees 90s run (Photo: AP)
Gene Michael, Architect of the Yankees the 90s run (Photo: AP)

Brian Cashman had little if anything to do with the success of those teams.

Gene Michael put together the Core Five of Mariano Rivera, Derek Jeter, Andy Pettitte, Bernie Williams, and Jorge Posada.

Other integral contributors to those teams included Yankees stalwarts Tino Martinez, David Cone, Darryl Strawberry, and David Wells – none of whom were brought on board by Brian Cashman.

The players played, and the players won. Yankees manager Joe Torre did his best to stay out of the way. Brian Cashman collected his rings.

The Boss Takes Matters Into His Own Hands (2009)

Fast forward eight years to consecutive seasons in which the Yankees managed two failing appearances in the World Series and four losses in the ALDS.

In 2008, the din of failure reached a crescendo when Brian Cashman’s roster failed to make the playoffs, finishing third, a full eight games behind the AL East leader.

Hal and George Steinbrenner (Photo: New York Daily News)
Hal and George Steinbrenner (Photo: New York Daily News)

Yankee Stadium was being torn down to be replaced by the “New” Yankee Stadium, a special project of George Steinbrenner, who was suffering from increasingly failed health.

It was then that The Boss, not Brian Cashman, took things into his own hands, saying, “enough is enough.”

Almost overnight, George Steinbrenner issued orders to Brian Cashman to add CC Sabathia and Mark Teixeria, two of the elite free-agents available following the 2008 season, plus A.J. Burnett as an addition to the rotation.

Sabathia came through big time with 19 wins, Burnett added 13, and ole’ reliable Andy Pettitte added 14 wins. Mariano Rivera finished 44 saves, and Merk Teixeria slammed 39 home runs and drove home 122.

Steinbrenner got his World Championship in a brand new Cathedral Of Baseball. Less than a year later, he would be dead, passing the torch (or so he hoped) to son Hal.

On His Own – Brian Cashman’s 13-Year Drought

A brief reprise of hope was offered with the Yankees Baby Bombers’ birth can be credited to Brian Cashman, resulting from the annual July College Draft.

But once again, we see performance standing below the hype of a new day.

The Baby Bomber - A Yankees Dynasty?
The Baby Bomber – A Yankees Dynasty?

Go down the list; who is left standing?

Aaron Judge is hanging on by a twig to a career that is far too close to becoming that of a mediocre, injury-prone ballplayer, who may or may not be worthy of pursuing in the final arbitration years for a contract extension.

As the best pure hitter on the Yankees, Greg Bird, who was once described by Brian Cashman, is now off the grid as Bird has all but disappeared from baseball.

Gleyber Torres has an “off-year” (or was it?) in 2020, both offensively and defensively. Stardom looms – but when and if will it come?

Gary Sanchez is a basket case by anyone’s neutral assessment. Nevertheless, Brian Cashman is poised to give the beleaguered catcher “one more try,” despite the lack of hope in anything seen by Sanchez’s performance in the Dominican League over the past two months.

Brian Cashman: A Sketchy History Of Trades

Consider first that Brian Cashman is responsible for trades that brought Lance Berkman, Tyle Clippard, Mike Lowell, Javier Vasquez, and Jeff Weaver to the Yankees.

Congratulated at the time, and while none of these players did anything to hurt the Yankees, nothing can be said for Cashman improving the team based on their contributions to the team.

Bill James once wrote that it takes five years to properly evaluate a trade. “There are trades where this is misleading, of course, “ he clarified, “but as a general rule, five years is quite enough for the direction of the result to be well established.”

Brian Cashman: A Revisionist’s History

So, as we look back on Brian Cashman’s giving up on top Yankees prospects in trades or designation for assignment roster moves, only to see them thrive in alternate environments, once again, re-thinking is warranted.

Trading both Michael Pineda and Justus Sheffield belongs on Brian Cashman’s resume as mistakes, with Pineda contributing to the Twins rotation and Sheffield coming along just fine with the Seattle Mariners.

The litany of questionable moves can go on, but the focus should be on asking a simple question of Brian Cashman – what have you done for us lately – on your own and without the prop of Gene Michael and George Steinbrenner?

Brian Cashman: Out Like A Lion Or A Lamb

Time is running out on Brian Cashman. More than likely, we will see him step down with an automatic “promotion” to an upper-level position in the Yankees front office.

Hal Steinbrenner & Brian Cashman - Blending Perfectly Photo Credit: The Captain's Blog
Hal Steinbrenner & Brian Cashman – Blending Perfectly Photo Credit: The Captain’s Blog

There should be no objection when that occurs.

His $25 million contract, approved in 2017, expires in 2022, and that will be an opportune time to make a much-need change in the GM position.

The unknown impact of Hal Steinbrenner’s insistence on the Yankees being in full-blown fiscal constraint.

If held, this translates to Cashman’s hands tied to a budget beneath this year’s salary cap (yes, that’s what it is) of $210 million before the luxury tax kicks in.

Given the Yankee’s exorbitant and previously committed salaries, with an over the top estimated payroll for 2021, Cashman still has a choice in the matter. Still, it will require an effort this writer (at least) feels is beyond the energy he has for the job at this moment in time.

Brian Cashman will go along to get along. He will follow lock, step, and barrel, letting the market play itself out with hope beyond hope that DJ LeMahieu will land in their lap.

That Luis Severino will return as a premier pitcher in the league sometime in June, and Domingo German not only has seen the light of his anti-social ways and hasn’t lost a step during an absence from baseball for more than a year.

That the Yankees will say rosaries hoping that Judge, Aaron Hicks, and Giancarlo Stanton will resist all odds, in the lineup more often than not.

Or, that Brian Cashman will go on record (privately) with Hal Steinbrenner with a message that says:

“We don’t have enough – even with LeMahieu -and you need to let me do my job – to spend more than you want – because otherwise, we are screwed for 2021.”

Brian Cashman: Riding Out The Storm

Beyond the believable? Probably.

But if I were Brian Cashman, I’d be thinking about my legacy as the Yankees GM, especially regarding a pending election to the Baseball Hall of Fame following retirement.

The current roster of the Yankees belongs exclusively to Brian Cashman. And in the days ahead, his legacy will be determined by our most recent memories of the Yankee’s success, or lack thereof.

As a fan of the Yankees, I go all-out for Cashman to succeed in bringing Number 28 to New York.

It’s just that when the emperor is stripped of his clothes, I’m not quite as convinced he’s still the man to get the job done.


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Author: stevecontursi

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