Peter J. Kaplan
8 min readSep 8, 2020

BRIAN CASHMAN

Brian Cashman has been the General Manager and Senior Vice-President of the New York Yankees since 1998 or, at the close of the 2017 campaign, for twenty seasons.

He began as an intern with the club in 1986, working in the minor league scouting department by day and in security at night.

After graduating with a major in history in 1989 from The Catholic University of America, a private university located in Washington, D.C., and where he was a four-year starter at second base for the Catholic Cardinals, the Yankees offered him a full-time position as a baseball operations assistant.

He gladly accepted.

Reporting to Phineas T. Bluster, aka “The Boss,” George Steinbrenner on any kind of regular basis would have to wait, which at first was to Cashman’s liking.

[“On July 30, 1990 Steinbrenner was banned permanently from day-to-day management (but not ownership) of the Yankees by MLB Commissioner Fay Vincent for paying a gambler named Howie Spira $40,000 to dig up “dirt” on [Dave] Winfield.”

(Steinbrenner had opted for the agreement that was tantamount to a lifetime ban — rather than the two-year suspension Vincent favored — because he believed that the suspension would cost him his position as a member of the U.S. Olympic Committee. As it was, he was reinstated on March 1, 1993, the owner’s second such reinstatement.

On November 27, 1974 then-Commissioner Bowie Kuhn suspended Steinbrenner following a felony conviction for making illegal campaign contributions to Richard Nixon. He was reinstated on May 1, 1976)].

But the 5’7” balding dweeb-like Cashman knew what he was getting himself into.

How could he not have known when in 1987 he witnessed GM Woody Woodward “buckling — Yessir, yessir, yessir — while the irate owner ordered that Woodward apologize for a trade that Steinbrenner had demanded?…

Cashman told himself, I would never want that job.”

No fewer than half-a-dozen bright, pedigreed and proud baseball minds — lifers — pushed through Steinbrenner’s perpetually revolving door during Cashman’s early-to-mid tenure and somehow he was — and is — the last man standing.

How?

He was smart, tough and willing to learn for starters.

And he had a sense of humor which has never left him.

Then, he called himself George Costanza, because his ascension to the assistant GM position in the early nineties conjured images of the bumbling, short and bald Yankees executive on Seinfeld.

Now, because after snapping at a reporter during a 2013 exchange that “Alex [A-Rod] should just shut the fuck up,” he showcases prominently on his desk a very well made Looney Tunes-like bomb figurine paperweight — wick unlit — with a lowercase f adorning the front.

He was not proud of his outburst, however.

“I blew my top. I got calls from managers, general managers, agents, players. They were all, ‘I’ve been wanting to say that, good for you.’ But I was embarrassed. I conduct myself, for the most part, at a much higher standard than that.”

Cashman’s rise began on a whim, somehow blossomed and has long since reached a full bloom.

He learned intensity in his household, growing up.

His father John ran away from home on Long Island as a youth to work horses, standardbreds.

Horse sales and auctions led to a twenty-year stint as general manager of the 2000-plus lush acreage of Castleton Farm in Lexington, Kentucky as well as Pompano Park in Florida, frequented by Steinbrenner and Whitey Ford among others.

Says Cashman’s mother Nancy, “Nothing was a holiday. When John and I traveled, we went to racetracks. Brian is like his father: It was business, period. Always on the phone.

Other people wouldn’t tolerate it, but that was right, you know? Doing business while you’re having dinner.”

Brian was the middle of John and Nancy’s five kids and everyone worked.

No fan of the horses to begin with, he became even less so when a blacksmith once handed him a hot horseshoe.

That pretty much sealed it; he was destined for the horseshit jobs around the stables — literally.

Apart from shoveling manure and placenta from the steaming stalls — he deigned to hold the tail while a vet went shoulder-deep into a pregnant mare’s womb — he collected barn garbage (on “maggot detail”) and the like, all-the-while struggling to avoid thrashing hooves and foot-long chomping teeth.

The safe haven for the twelve-year-old, the escape, was baseball.

Thank God for baseball.

When he somehow found himself locked into and not out of an emptied Riverfront Stadium in Cincinnati as a boy he told his anxious parents through a gate to “pick me up tomorrow!”

He became one of Catholic’s best players, hitting leadoff and manning second and in 1988 Cashman set the school single-season record for hits with 52 in 38 games, a mark that stood until 1999.

His lack of size was no deterrent to him, in fact it was a non-issue altogether.

He was the first one to defend honor in a barroom disagreement and also quick to bark across the diamond and into an opposing dugout something to the tune of “One of yours is going down for that!” in protest of a questionable slide.

Observed Matt Seiler, Cashman’s double-play partner, “any challenging situation, Brian was right there in the middle, and he would step in front. He was very serious, very intense. A very good judge of people. We’d meet someone the first time and say, ‘This guy seems nice,’ and he’d say. ‘No, he’ll let you down. This guy doesn’t have what it takes.’”

His makeup seemed ideally and uncannily synced to what would become his career path.

Cashman had connections through his father’s track associations to be sure, and once he was settled into his job as an assistant in baseball operations following graduation in ’89, he was like a sponge.

Former Reds and Nationals GM Jim Bowden, at the time two months into his job as a Yankees assistant senior VP, vividly recalls Steinbrenner walking Cashman into the baseball ops office and interrupting a group including Gene “Stick” Michael (who died on September 7th at 79 and was a wonderful mentor to Cashman), Lou Piniella, Bob Quinn, Dallas Green and Syd Thrift to make the introduction.

“I want to introduce you to Brian Cashman,” The Boss said. “His dad is a good friend…[and then in typical Steinbrenner-esque fashion] and someday you’ll all be fired and he’ll be the general manager of the Yankees.”

Everybody present laughed and three months later Bowden was casualty number one.

When Steinbrenner began his 1990 suspension and Michael assumed the daily operations of the club, Cashman sagely and quite naturally made himself indispensable, which was not lost on Michael.

“Brian knew everything going on,” Michael remarked. “Nothing slipped by.”

‘Nothing slipped by’ because Cashman was hungry; certainly not hungry to be known, but hungry to succeed.

He wanted to do well for himself, his family and for those who blessed him with this unique opportunity — George Michael Steinbrenner III, being at the top of the list.

Cashman served as Michael’s assistant GM in the early nineties and when he was named the Yankees GM in 1998 succeeding Bob Watson, he continued to rely on Michael’s perspective, counsel and boundless baseball knowledge.

Michael’s willingness and ability to absorb new information as well as his backbone when it came to telling The Boss not what he wanted to hear but rather the hard, unvarnished truth at any cost, also mightily impressed Cashman.

He reflected that “[Michael] was a scout with an eye for talent and George was emotionally reactive to items in the short term.

But George Steinbrenner saw something in Gene Michael.

He gave him opportunities as a coach, manager, scout and GM. He kept him around because he needed the direction and approach that Stick offered.

Even when he was fighting with Stick on plenty of things, George still recognized that Gene Michael had a gift that made George Steinbrenner and the Yankees better.”

Cashman continued, “Looming over every move with George was him saying, ‘You better be right.’

And Gene Michael was mostly right. That is the most significant thing of all. When the dust settled, Gene Michael was mostly right.”

Perhaps equally impactful was Michael’s advice to Cashman to ‘never lie.’

Sacrificing one’s integrity and exacerbating a problem by lying was simply not worth it because the truth always comes out.

A concise ‘no comment’ was the preferred retort to extricate oneself — and the organization of course — from a sticky or delicate situation.

As Cashman remembers, Michael’s mantra was, “You don’t have to confirm or deny…Let them try to confirm it elsewhere, but don’t lie.”

In dealings with Steinbrenner, Cashman eschewed the conventional in-house wisdom which strongly suggested that if you saw The Boss coming, you went the other way.

Instead he found ways to push back, sometimes gently but not always.

In spite of recognizing the very real possibility that he would never make Steinbrenner happy, Cashman persevered.

He had become one of The Boss’ favorite whipping boys early on, the subject of humiliating abuse and the recipient of never-ending phone calls.

“Who asked you? You’re just a fucking clerk,” Steinbrenner sneered at Cashman during one front-office meeting.

Cashman filed that away for future reference.

When details from an organizational meeting found their way into the pages of the Daily News and the New York Post about a month later, Steinbrenner went berserk.

“Who’s leaking this shit?” he demanded at the top of his lungs. “Was this you Cashman?”

“No,” Cashman screamed back, waving a fistful of paperwork. “This says it was a ‘high-level Yankee official.’ “I’m just a clerk, remember? I’m just a fucking clerk!”

Steinbrenner liked that.

The Yankees have won seven American League Pennants and five World Series since 1996, 6 and 4 respectively under Cashman, the GM.

A .594 Winning Percentage.

Winning an average of 96 games per season.

Missing the playoffs but 3 times.

Those who choose to knock him assert that the early teams were not assembled by Cashman; the talent did not boast his signature, but rather Michael’s or even the more dramatic imprint of others.

Watson for one found that laughable.

“He survived in the biggest sports city in the world, the biggest media center, working for the toughest owner in the world — and delivered how many world champions? The Yankees have been relevant since ’95. We’re talking about the kind of baseball man he is, and the type of man. He’s a survivor. A winner.”

No General Manager under The Boss had more clout either, ever.

Billy Beane said, “If anybody else had done what Brian’s been doing, you know what’d be in front of his name? Future Hall of Famer. There was a time I voted for him for Executive of the Year every year, regardless.”

Brian Cashman, he of the unbridled adrenaline, humanitarian bent and overall joie de vivre — rappelling down a Stamford, Conn. high-rise in an elf costume or sleeping on a sidewalk to raise money for homeless youth, skydiving or even unleashing the sounds of his hidden fart machine on unsuspecting NYC pedestrians — will either make it to Cooperstown or not.

Just 5 GMs have been inducted to the National Baseball Hall of Fame: Ed Barrow, Branch Rickey, George Weiss, Larry MacPhail and John Schuerholz in 2017.

Certainly Theo Epstein will be a first ballot lock.

It shall be what it shall be.

But when he looks in the mirror — his life’s imperfections aside, and may he join the club on that — he ought to be happy with what he sees and thank his parents.

And his lucky stars.

After he takes a very deep breath, I suppose he ought to look upward and thank Steinbrenner too.

[Editor’s Note: This piece was written by Mr. Kaplan in September 2017.]

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