How to survive 22 years as Yankees GM? Brian Cashman can thank his Hall of Fame father

Astros, Dodgers, Yankees facing no threats from below (1:41)

Ryan Howard and Tim Kurkjian discuss this week's MLB power rankings, with playoff matchups a central focus as the regular season winds down. (1:41)

NEW YORK -- Brian Cashman told a story about a horse named Nifty. Cashman hated his summer job on his father's farm in Kentucky, hated mucking out stalls and cleaning fecal stains from barn walls with his bucket of ammonia and oversized brush. Young Brian loved baseball, and he wanted no part of his old man's life as one of the best breeders, traders and horse whisperers around.

Then he met Nifty. Before he would leave Lexington to study and play ball at Georgetown Prep in Maryland, the 5-foot-7 Cashman was charged to break in this brown quarter horse that was a lot bigger than he was. He would introduce Nifty to a saddle, lay on her back, and the horse would try and try to throw him off. Cashman said the process took at least six grueling weeks in the oppressive heat, but sure enough they bonded and he could finally ride that horse out of the stall and into an open field.

Cashman later got word at school that Nifty missed him dearly. In fact, Nifty wouldn't let anyone else in the saddle but the kid who couldn't wait to get a million miles away from those barns.

"One of the greatest experiences of my life," Cashman said of breaking in that horse.

He was sitting in his Yankee Stadium office near the end of a season that has constantly kicked and thrashed at him like old Nifty, forcing the 52-year-old general manager to hold on for dear life. Cashman was talking at around the time he learned that reliever Dellin Betances' season would be a one-and-done proposition, thanks to a freak Achilles injury, and that Major League Baseball was placing his 18-4 pitcher, Domingo German, on administrative leave while it investigates a domestic violence allegation against him.

The Yankees have watched an MLB-record 30 players go on the injured list this year, costing them, according to Spotrac, more than 2,500 days of service while those players earned more than $80 million. They won the American League East anyway, despite (or because of) Cashman's offseason choice to stay clear of Manny Machado and Bryce Harper. They won 102 games (and counting) despite his midseason choice to stand pat as his biggest threat from here to a parade, the Houston Astros, added Zack Greinke and compelled The New York Post to portray Cashman as a zombie to illustrate its back-page headline, "The Walking Deadline."

The Yankees' starting rotation might yet compromise their bid to win it all. But the moves Cashman did make in the offseason and late last summer -- for the likes of DJ LeMahieu, Adam Ottavino and Gio Urshela -- fortified a roster deep enough and flexible enough to overcome the staggering list of injuries, and to inspire an interesting question.

After Cashman won a dozen division titles and four World Series rings in his previous 21 seasons as the Yankees' GM, was this his best work ... ever?

"You could flip it and say, 'Is this my best or my worst?'" he said through a laugh. "I got 30 guys hurt. I picked a lot of broken guys."

The GM was the Yankee who didn't break, even after some overheated Connecticut cops pulled guns on him in August while mistaking him for a thief who had stolen Cashman's Jeep Wrangler. The GM thanked police for their efforts and dismissed the whole incident, if only because he has proved one thing, above all, across all these years of running the most relevant team in the most volatile market:

You can kill Cashman. You just can't kill him off.

"I expected to be attacked," he said of the zombie depiction, not the cops, after his trade deadline inaction. "I expected to be publicly humiliated and ridiculed. I didn't react to it. I've grown thick skin. I understood the context, and I can appreciate the humor it provides. ... I made tough decisions not to do what I consider horrible deals on players that, if we imported, I didn't think would make any difference whatsoever but would cost us a lot in talent. Basically if I did it, it would be to cover my ass ... Everything I wanted didn't get moved. And the stuff that did get moved hasn't played out as well as I think people would have hoped in their world."

Cashman figured out long ago that the cover-my-ass approach wouldn't get him very far in New York, which is one reason Marcus Stroman ended up with the Mets. (Stroman took a Twitter jab at Cashman on Tuesday in response to the GM telling Yahoo the Yanks would have used the starter in the postseason bullpen.) Only Ed Barrow, Yankees GM from 1920-1945, has survived longer in the job, and Barrow didn't have to fight octagon matches with George Steinbrenner. In Cashman's Yankee Stadium office, isolated on a wall near the door hangs a simple framed profile shot of The Boss sent by a fan who found it while cleaning out his garage. The GM put up the picture because, he said, "I didn't have anything from The Boss, and he had a massive impact on my life."

This photo of the late owner, with one forbidding eye still locked on his underling, advances the narrative of Cashman as a scarred product of Daddy Steinbrenner, whose volcanic eruptions hardened the GM for the battles to come with Alex Rodriguez, Derek Jeter, Joe Torre and the New York tabs. But Cashman's toughness shouldn't be traced to Steinbrenner. It should be traced back to that horse farm in Lexington, Kentucky; Castleton; and to a man who had tangled with the Yankees' owner before assigning Brian to go one-on-one with Nifty.

The man who ran a storied franchise in the bluegrass with the same firm hand his son uses to run a storied franchise in the Bronx.

AT 16, AFTER squabbling with his father over his career ambitions, John A. Cashman Jr. ran away from his Long Island home. He was not interested in college, or in following his dad as a stockbroker on Wall Street. John wanted a piece of his dad's second career -- John Sr., a father of nine, was also a presiding judge at Roosevelt Raceway. John Jr.'s dream was to become a horseman.

He reportedly spent his runaway time at New Hampshire's Rockingham Park, and did some grooming, training and driving for the harness Hall of Famer, Delvin Miller, in Pennsylvania and Orlando. In 1959, after winning three races as Vida Hanover's driver, the 19-year-old Cashman was named assistant racing secretary at Vernon Downs in Central New York. Two years later, Cashman became the country's youngest racing director, at Roosevelt, at a salary of $12,500. He helped pack a defining New York venue at a much younger age than his son would; Brian, at 30, would become baseball's second-youngest GM ever in the winter of 1998.

John Jr. was in the Army Reserve when he was set up with a Long Island girl, Nancy Pratt, who used to show her horse in local events. Their blind date took place at the racetrack, of course. They married in 1963 and effectively lived at Roosevelt. "It was big-time back then," Nancy said. "We would get 30,000 or more fans at night. ... John was so driven, just like Brian would be in baseball. He worked day and night. He'd wake up and it was all about the horses."

"If we were struggling or if George [Steinbrenner] was on my ass with the latest complaint or problem, just crushing me, my dad would just say, 'Hey man, you can handle it.' He'd prop me up. He'd tell me, 'Keep fighting. Just stick with what you believe. Tell him what you think.'" Brian Cashman on his late father, John

The third of what would be five Cashman children, Brian was seven months old when his father left Roosevelt after six years to make more money breeding and selling. John was part owner of the stallion Speedy Streak, the Hambletonian champ. The Cashmans lived in Goshen and Washingtonville, New York, for 10 years, and life was good, except when it wasn't. John had to defeat his most daunting opponent -- alcoholism. "The children were young," said Nancy, now 77, "and he just had to shape up, and he knew it. He did it by himself. I was very proud of him."

Nancy said her husband was sober for the last 40 years of his life.

Brian didn't know his old man was an alcoholic until he opened a drawer in his office one day and found literature on a path to sobriety. He never asked his dad about it. "We were the old Irish family," Brian said. "Whatever your problems are, you don't talk about it."

John Cashman got his big career break in 1980, when he was asked to become general manager of Castleton Farm. "A beautiful show place," said longtime horseman Bob Boni, a close friend of John Jr.'s. "The Yankee Stadium of harness racing."

Cashman was widely regarded as fair, personable, relatable. He was genuinely liked by those beneath him on the organizational flowchart. And yet he was never afraid to speak his version of the truth. Brian Cashman witnessed his father making tough calls while in charge of the country's premier standardbred farm. John once fired an employee out of necessity, Brian said, and that employee "went on a bender and then called the house and said, 'I'm going to kill you and your family.'" Brian recalled seeing a police car parked outside the family's home.

"Most people are wired in a way to avoid conflict," Brian said, "and my father, like everybody, was willing to do that. But when circumstances dictated it, he would not allow bulls--- to fly. He was allergic to bulls---."

John Cashman ran Castleton for more than two decades, and Brian likened his eye for talent to that of Gene Michael, the scout who helped shape the Yankees dynasty of the 1990s. Brian thought horse people had the same reverence for his father's scouting ability that baseball people had for Michael's. "He could spend a whole day watching a horse jog and break down his gait," Brian said, "and somehow get insight into his soul. He'd be able to tell you if that horse was someone he'd be willing to place bets on in terms of purchasing, or recommending someone to buy a piece of that horse or not."

Bob Boni never met anyone with a better read on horses and the people who managed them. In fact, after spending half a century in the industry, Boni, the owner of New Jersey's Northwood Bloodstock, called Cashman the greatest harness racing executive of all time, hands down. John was inducted into the harness racing Hall of Fame in 1992.

Cashman helped create the Breeders Crown series and ran the United States Trotters Association, and he won too many awards and served on too many important councils and boards to count. He oversaw various properties under the Castleton umbrella, including Pompano Park, just north of the Yankees' spring training base then in Fort Lauderdale, Florida. Cashman had established a number of friendships with railbird ballplayers, including Yankees great Whitey Ford and former Dodgers pitcher Ralph Branca, who had landed young Brian a bat boy job with his old team. The horse game also connected John to Steinbrenner, a notoriously bad loser on the ballfield and at the track.

"Normally John and George had a good relationship," Nancy said. "Except one year George didn't think John sold him the right horse. For three months the horse wasn't doing well, and George didn't pay the sales company. He wouldn't talk to John until he took back the horse. And then the horse started doing well, and he talked to John again."

Brian recalled his father standing up to Steinbrenner every time the owner wanted his money back on a losing horse. He said his old man also refused a Steinbrenner request to fix a celebrity drive in advance so the Boss would end up starting on the inside rail.

Brian's older brother, John III, trained horses for Steinbrenner for five years and called that period "a nightmare." John III said his father warned him that he shouldn't train for the owner, that The Boss had a long history of refusing to pay his bills. Steinbrenner screamed at John III once when their horse got beaten by a nose. "He finished second!" John III responded. "You know what second is?" The Boss shot back. "The first horse to lose."

"Most people are wired in a way to avoid conflict, and my father, like everybody, was willing to do that. But when circumstances dictated it, he would not allow bulls--- to fly. He was allergic to bulls---." Brian Cashman

Steinbrenner made up for his attacks on John III by hiring his younger brother in 1986. Brian was on a Florida trip, playing Division III ball for Catholic University, when he lost all his travel money in a high-low card game. His father told him to head over to Pompano, where track publicist Allen Finkelson would loan him some cash. Finkelson told Brian that he was Steinbrenner's best friend before asking the college freshman what he had planned for the summer. "I'm going to play in a summer baseball league," Cashman said.

"What if I get you an internship with the New York Yankees?" Finkelson asked.

Cashman was a Dodgers fan who despised the Yankees; he eagerly took the job anyway. He was a gofer by day, and a 160-pound security guard hauling drunks out of the stands by night. "My brother was very much like my dad," John III said. "They both climbed the ladder from the very bottom to the top."

The top, for Brian, was Steinbrenner's stunning offer for him to become Yankees GM after Bob Watson decided he'd had enough of The Boss' verbal abuse. On the day he was promoted, Feb. 3, 1998, Cashman had the nerve to admit at his news conference that he was an administrator who didn't consider his scouting ability a strength. He also had the nerve to announce that he didn't believe star center fielder Bernie Williams was worth the money he was seeking.

Steinbrenner had blown through more than a dozen GMs in 25 years of ownership, and it was hard to see Cashman lasting longer than Watson did. But on the phone from Castleton that day, John Cashman said he was putting his money on his son to beat the longest odds.

"Whitey Ford told me Brian has the perfect personality to deal with George," John said. "I happen to agree with him."

IN A QUIET moment at his desk last week, as he faced a wall covered with the names of every player in his system, Brian Cashman's voice wavered when he talked about his father's final days in 2012. John had been diagnosed with pancreatic cancer, and Cashman had enlisted the help of Yankees president Randy Levine and MLB commissioner Bud Selig in getting him the best available treatment. John agreed to be flown out to Arizona for an assessment. "He did everything we wanted him to do to try to beat this thing that was unbeatable at the time," Brian said.

A lifelong Yankees fan, John closely watched his son's club every day as he was dying. "He would lose himself in how the team was competing on a daily basis," the GM said. Brian played his father's favorite Frank Sinatra and Alabama songs in John's final hours in hospice. John didn't often express how he felt about his son and his four siblings -- "It's just not the Irish way," Brian reminded. But the GM appreciated it when a few mourners at the funeral pulled him aside and told him how proud his father was of everything he'd accomplished.

"I used to tell John, 'You used to be a big-shot harness racing executive, and now all you are is Brian Cashman's father,'" Boni said. "And every time I told John that, he loved it."

John Cashman used to start his day by checking in with his three sons and two daughters. With Brian, the conversation usually revolved around Steinbrenner. The Boss forever threatened Brian's job, berated him for allegedly getting outfoxed by counterparts and ordered him to perform humiliating tasks -- John III said Steinbrenner once demanded that his brother personally collect the players' spring training rental car keys before they headed north.

Brian wasn't hesitant to punch back, and to trade F-bombs with his employer. His father always knew the right thing to say to temper the storm. "If we were struggling or if George was on my ass with the latest complaint or problem, just crushing me," Brian said, "my dad would just say, 'Hey man, you can handle it.' He'd prop me up. He'd tell me, 'Keep fighting. Just stick with what you believe. Tell him what you think.'

"He had this little way of just telling you to keep getting after it, and doing what you think is right, and you will be fine. But there were many times I was ready to move on. George Steinbrenner was as great an owner as you can have, but as difficult a boss as you can have also. And because of that roller coaster ride of emotions, my dad was always there to counsel me or guide me. I know he never wanted me to leave the Yankees. He was really proud of that."

So Brian Cashman never did leave the Yankees. He has no timetable on how much longer he wants to do this ("Just living in the moment," he said); he's been their GM longer than Bill Belichick has been head coach of the New England Patriots. During Cashman's time running the Yanks, the Mets have had six GMs, the Jets have had six and the Knicks have had eight. Cashman has survived the transition from the old Yankee Stadium to the new Yankee Stadium, from George Steinbrenner to Hal Steinbrenner, from a philosophy of spending opponents into oblivion to making the money smarter through analytics. As much as anything, he has survived nine seasons without a World Series title, an eternity in the Bronx.

"I used to tell John, 'You used to be a big-shot harness racing executive, and now all you are is Brian Cashman's father. And every time I told John that he loved it." Bob Boni, longtime horseman and family friend

But Cashman has averaged 95 victories over his 22 seasons. He is chasing his sixth World Series ring, his fifth as GM, and his first without Jeter and Mariano Rivera, the iconic cornerstones acquired by other executives. If Cashman wins another championship with a third manager (Aaron Boone would join Torre and Joe Girardi), it might make him a mortal lock to match his father as a Hall of Famer. Cashman says he never thinks about the Hall and cannot fathom a place in a Cooperstown that doesn't include The Boss. In fact, he can't understand why recent Yankees inductees (including Torre and Rivera) haven't used their platform to campaign for the owner. "Why don't you openly talk to why is he not here during your induction speech?" Cashman asked.

Steinbrenner is always there, somewhere, in Brian's mind. So is his old man. He thinks about John Cashman every day. Brian is proud that the Meadowlands named a race after him, and that his daughter, Grace, sang the national anthem before it as a tribute to her grandfather. The GM still laughs over the notion that his dad "broke every child labor law" when Brian worked garbage detail at Castleton, or when Brian had to hold up a pregnant mare's tail while a veterinarian dug deep to inspect the health of the foal.

"He was a tremendous father," the GM said.

Brian replicated his work ethic. He said he either inherited or innately learned John's willingness to make tough choices and to say things important people didn't want to hear. When Brian ordered Jeter to fix his defense and his relationship with A-Rod, and challenged The Captain to test the market during turbulent contract negotiations, longtime horsemen knew that sounded just like John Cashman's son.

Given that the Cashmans have always lived by the scoreboard, a question needs to be asked: Who's the better sports executive, John the father or Brian the son? "A toss of the coin," said John III, the family member. "I'll make it a dead heat," said Boni, the family friend.

Maybe October will end up being the tiebreaker, maybe not. Either way, Brian Cashman will honor his father as tries to ride this pinstriped pony home.