As Yankees’ General Manager, Brian Cashman of Darien has what many consider to be a dream job, but keeping everybody happy — especially the “Boss” — makes it demanding too.
Grace Cashman, age seven, has everything planned. When her daddy, Brian, leaves his current job, his cellphone will be laid out on the driveway of his family’s Darien home. Her mom, Mary, will climb into their SUV. Then Grace and her brother Teddy, age two, will watch as the auto transforms the phone into cellular pâté.
“She’s not joking,” Mary says. “She’s serious.”
Not that Grace doesn’t like it that her father is general manager of that most legendary of sports franchises, the New York Yankees. But that cell- phone can be distracting. When she’s got him locked in a snowball battle on some winter’s day, he’s simultaneously carrying on a conversation with some agent or a scout or a man he calls “the Boss.” You try making a snowman with somebody who’s trying to make Johnny Damon a Yankee at the same time. It’s hard.
“My winter is harder than my summer,” Brian notes. “It’s all a lot of work, but the winter is that much more, going head-to-head on free agency, arbitration and trades.”
But while his pinstripe dedication may annoy Grace, it pleases others, chief among them the Boss, a.k.a. George Steinbrenner. In his thirty-three years as the Yankees’ principal owner, Steinbrenner has gone through about as many general managers as Spinal Tap has drummers. Only Cashman, in his ninth year as GM and just signed to a new contract, has lasted this long.
It probably helps that the Yanks have finished atop the American League East every season he has been there, have won three World Championships in a row, and are widely considered the class of baseball in 2006.
“Brian, from what I’ve seen, is highly respected by the people in his profession not only for his business acumen but also for his ability to work for George Steinbrenner, who is extremely difficult to get along with and apparently remains as volatile as ever,” says ESPN commentator Jeremy Schaap. “How he’s managed that relationship has been very impressive over the years.”
Joe Torre, the Yankees manager since 1996, says Cashman has “his finger on the pulse” and a “non-stop work ethic.”
“It’s like a play on Broadway, and he’s the director,” Torre says of Cashman.
Just because it’s a dream job doesn’t mean it’s been easy. Even in Cashman’s first three seasons with the Yankees, 1998–2000, when the team won back-to-back-to-back World Series contests, Steinbrenner’s reported rages made tabloid headlines. Since 2000, the Yankees have reached the World Series twice, losing to the Arizona Diamondbacks in 2001 and the Florida Marlins in 2003. They have won their division every season since Cashman became the surprise choice to succeed Bob Watson just before the 1998 season. That’s an unprecedented run of success even for the Yankees, but it’s not enough for Steinbrenner or the team’s success-spoiled fan base. Nor is it for Cashman.
“Most of the pressure he puts on himself,” Mary says. “He wants to win. He wants to win for the team, and he wants to win for Steinbrenner.”
And “winning,” she adds, doesn’t mean a playoff berth or a division title. Off-seasons without a World Series triumph can make for sad days around the house, she claims, especially after the Boston Red Sox took the crown in 2004.
Walking into the team offices at Yankee Stadium is to understand how that mentality got inculcated into Brian, who turns thirty-nine July 3 and has worked for the Bronx Bombers since college. The hallway outside his office is lined with framed photographs of assorted Yankee legends and winning teams. Even looking at the floor offers no relief: Embossed in the blue carpeting at short intervals are each of the calendar years since 1923 that the Yankees captured the Major League crown. You almost run out of corridor before you run out of years.
Yet this eminent front stops the moment Brian invites you into his office. Dressed in jeans and a short-sleeved print shirt, Cashman radiates preternatural calm. He looks positively unassuming with his wiry build and thinning brown hair, and his voice, with its Kentucky twang, just carries across his small office. But his frank, keen gaze commands immediate respect, and his intense blue eyes bore in.
It used to be that baseball GMs were grizzled ex-ballplayers. Now they tend to be young Ivy League types, whose teen years were as likely to have been spent playing Dungeons & Dragons as baseball, and who forsake gut instinct for statistical data. While one of the youngest ever to be named a Major League general manager, Cashman’s more a throwback than you might guess. A baseball star at Catholic University of America in Washington, D.C., he held the school’s single-season record for base hits and nursed dreams of playing in the majors until he got a job as a Yankees intern.
“Working here allowed me to see the big picture — how many talented players are out there and how not very good you are,” he notes.
Cashman grew up in Lexington, Kentucky, the son of Nancy and John. His dad raised standard-bred horses for harness racing, and Brian and his four siblings were kept busy performing odd jobs.
“My father broke every child labor law,” Brian says with a shake of his head. Cleaning stables, he says, “gave me a work ethic and made me realize how tough it was to get by.” It also gave him a profound distaste for horses. He preferred basketball and baseball. His favorite baseball team was the Los Angeles Dodgers. Brian rejoiced when they beat the Yankees in the 1981 World Series.
“At that time I was one of the all-time Yankee haters,” Cashman admits.
Fate was about to play a funny trick on him. At a racetrack his father managed in Florida, the publicity director, a man by the name of Allan Finkelson, was a close friend of a horse-racing enthusiast named George Steinbrenner. While Brian was in college, Finkelson landed him a Yankees internship.
“Our conversations were ‘always keep your nose clean, work hard, and the sky’s the limit,’” John Cashman recalls. “Hours mean nothing to him — sometimes unfortunately.”
Cashman interned with the Yankees every summer during college, updating roster displays in the daytime and helping security escort unruly fans by night. He was offered a full-time job upon his graduation in 1989, which he accepted thinking that it would come in handy when he applied to law school a year or two down the road.
For a period Cashman worked in player development in Tampa, Florida, Steinbrenner’s operational base and a vital cog in the Yankee apparatus. “Once he started working in Tampa baseball operations, a lot of doors opened,” says John Cashman.
Brian impressed many with his spongelike ability to absorb and retain information.
“If you had a conversation and Brian was there, you could talk to him about it later on and he would remember everything about it,” recalls Gene Michael, twice the Yankees’ manager and twice general manager in the Steinbrenner era. It was during his second stint as GM that Michael made Cashman his assistant. “It was like having a partner,” Michael says.
Cashman by this time understood the challenge of working for the Yankees and its owner. He saw other GMs chewed out over flop trades or a specific game Steinbrenner was unhappy about and remembers thinking that GM was one job he never wanted. But when he was asked to replace Michael’s successor, Bob Watson, just before the 1998 season, Cashman had only one question: What did Mary, then his wife of just over two years, think?
Mary, by her own admission no baseball fan, was firm. “I told him, you’ve got to do it. You gotta try.”
Mary knew Brian from their college days, when both traveled in the same large circle of friends. Yet they didn’t know each other well. Then Mary noticed Brian staring at her at a 1992 Homecoming. Brian wanted to introduce himself but couldn’t work up enough nerve. “I’m shy, whatever you want to call it,” he says. He vowed that he would say hello if he ever saw her again.
Opportunity knocked again a few days later at a Manhattan bar. “It was weird,” he recalls.
“I finally got the courage to go over and talk to her, and it looked as if she saw me coming and turned away. I said ‘Whoa,’ and gave up.”
He was heading outside when Mary, battling her own shyness while keeping an eye on Brian the entire night, sent a friend to intercept him. The two hit it off fast after that. “It was his sense of humor,” she says. “He seemed like a good guy.”
Two years later Brian took Mary to meet his parents at Castleton Farms. For about the only time in his life, he found horses came in handy, distracting Mary while he got down on his knee to surprise her with an engagement ring. They were married in 1995.
Being GM would bring him much glory and stress, not to mention long work hours driven by his own fear of failure as much as by Steinbrenner’s fabled wrath. “Right now, while I’m talking to you, one of my competitors could be on the verge of completing something that will make the difference,” Cashman says.
Every now and again, conversation is interrupted by a call, usually a reporter asking about the status of a couple of injured starting pitchers. While he may be in the media crosshairs for going on a decade now, there’s little evidence of caginess.
“There are people who take some shots I don’t like, but then I go to the archives and find the same people have written some very positive things too,” he says. “I’m not saying I’m perfect at this, but I’ve gotten better.”
It was an ex-Yankee named Leo Durocher who coined the normally unassailable phrase “Nice guys finish last.” Yet Cashman has gotten where he is without losing his reputation for being exactly that: nice.
Ross Natoli has been Catholic University’s baseball coach for twenty-one years; Cashman was his starting second baseman for four seasons. He recalls Brian as a “quiet and intense competitor” who earned the nickname “Crash.” Today the coach sees that same mentality in his former player’s approach to the Yankees GM job, leavened by respect for players, executives and fans alike.
“I’m prouder of the person he became than the accolades he’s deserved,” Natoli says.
When she worked as a player agent, Jean Afterman clashed with Cashman over the contracts of players like Hideki Irabu and Alfonso Soriano. Yet Cashman was impressed by her tenacity. “She was so sharp and tough in negotiations, I always had it in my mind that I wanted her on our side of the fence,” he says. He hired her as assistant general manager in 2001.
“Brian is uncomfortable with the nice things you say about him, but those same qualities come through whichever side of the fence you’re on,” she says. “He has a strong sense of integrity, what’s right and wrong. If there’s a misunderstanding, there’s no ego involved. That’s one of the most significant things about him. He’s confident, and he should be. He has nothing to prove. Brian is very comfortable in his own skin.”
Jean Afterman is one of only three women to have held the position of assistant general manager in the majors. Two of those women — Jean and her immediate predecessor Kim Ng (now with the Los Angeles Dodgers) — were hired by Cashman. Keith Hernandez may not like them in the dugout, but Cashman is fine with women in the front office.
“It’s Brian recognizing the value and merit of somebody and being gender-blind about it,” Jean says. “A lot of men are not comfortable working with women, especially in sports. That’s not an issue with Brian.”
Acquiring on-field talent is another chief concern. Trading David Wells for Roger Clemens in early 1999 brought the team one of baseball’s greatest pitchers at the peak of his game and sent a message that the 1998 World Champs would not rest on their laurels. A call to the Cleveland Indians assistant GM in the middle of the 2000 season about giving a former Yankee bullpen catcher a 1999 World Series ring yielded David Justice, who became the Yanks’ 2000 postseason hero.
Late one evening in February 2004, Mary woke up to the sound of Brian talking excitedly on the cell phone in their bedroom. He was finalizing a deal that would bring Texas Rangers shortstop Alex Rodriguez to the Yankees. Now in his third season as the team’s third baseman, having changed positions at Cashman’s request to accommodate shortstop Derek Jeter, Rodriguez was 2005 American League Most Valuable Player and is considered one of the two or three best players in the game today.
“Alex was huge,” Cashman says.
“I remember telling George Steinbrenner, ‘Boss, this is a can’t-miss move.’”
In the last off-season came one of Cashman’s biggest gets yet, luring Red Sox star Johnny Damon to New York in a move that immediately drew comparisons to the Yankees’ buying Babe Ruth from their Beantown rivals seventy-six years before.
“Johnny Damon not only gave the Yankees a centerfielder, it took a centerfielder away from the Rex Sox,” says Dave Anderson, a Pulitzer Prize–winning columnist for the New York Times. “It was a very slick deal.”
Last season was the Yankees’ rockiest since Cashman’s arrival, with injuries and underperforming players abounding. Cashman describes his roster moves in 2005 as part inspiration, part desperation: “When people asked me why I got Shawn Chacón, I told them, ‘Well, I needed a pitcher for Saturday.’”
But Chacón, Aaron Small, and other players Cashman brought in made a huge difference. Torre touts 2005 as Cashman’s best season.
“No question,” Torre says. “The support I got from Brian was critical. He was the one who brought in Robinson Cano over the objections of some of my coaches, which worked out well. It’s always turbulent with the Yankees. I think he did an outstanding job, keeping the waters as calm as you can keep them.”
“They’re considered a team, a daily double,” Anderson says of Torre and Cashman.
“They need each other, and they get along so well. They’re not blustery. They can sort things out.”
“I like our relationship,” Torre says. “We don’t agree on everything, but that’s fine.”
Cashman may have the smarts for deals, but he’s got the bucks too. The Yankees’ payroll has long been baseball’s largest, and by a wide margin — $198.7 million this opening day in comparison to the Red Sox’s second-place $120.1 million. It’s a huge advantage, though not the guarantee some may think.
“Yes, they have the blank check,” Schaap notes. “But that was also the case between 1982 and 1996, when the Yankees never won a pennant. The fact that they’ve been in the play-offs every year since 1995 is a testament to that checkbook mentality, but also their ability to keep people happy and make good acquisitions. Look at the Mets, the Rangers, the Knicks — all are at or near the top of their respective sports in terms of team salaries but are not regular play-off contenders like the Yankees.”
Near the end of the 2005 season, Cashman had another contract to work on: his own. It wasn’t just five straight non-championship seasons that were the problem, but interference with the way he did his job. Cashman won’t specify where the problems came from, but media reports noted Steinbrenner and his Tampa-based support staff were making player deals over Cashman’s objections.
“We’re all accountable to Steinbrenner as owner, but to be an effective leader, your subordinates have to know you’re in charge,” Cashman says. “I wasn’t staying unless I was going to have the ability to do the job. You can’t have a situation where you are undercut by people who are supposedly below me in the chain of command.”
The final contract, which spells out Cashman’s final authority over the Yankees’ roster, runs for three years and pays a reported $5.5 million. The cell phone got a reprieve from Grace.
“I don’t want to say it was expected,” Mary says. “It was more of a relief. Now we have kids in school. We finished renovating the house. It’s definitely more difficult to move now.”
The Cashmans lived in Darien from 1996 to 2000, then moved to a larger house in Scarsdale, New York, after Grace was born. They moved back to Darien in 2002.
“We missed Darien,” Mary notes. “My twin sister, Maureen, is here and I missed her. My older sister Colleen lives in New Canaan, so she’s close by, too.”
Brian says Darien is as close as he can get to Kentucky in this job. “It’s a little slower, quieter and more peaceful. We like the restaurants here and ice skating at the Twin Rinks in Stamford.”
Other favorite stops include the Sugar Bowl, Maritime Aquarium in Norwalk and Valbella in Old Greenwich. A set of golf clubs hangs in his garage, but Cashman doesn’t get to use them much. The only hobby he does indulge is keeping fish. A couple of years ago Mary bought him a 370-gallon salt-water aquarium. It’s the one pastime that allows him to simultaneously watch games and work the phone.
Mostly he hangs out with Mary and the kids. “He gets up with them on the weekends, he drives Grace to school,” Mary says. “When he’s home, he does everything with them. He’s not sitting in front of the TV and watching football.”
At Yankee Stadium Cashman has his own private box, connected to his office, which seats six. That doesn’t include Brian, who stands throughout the game.
“Fans don’t have the behind-the-scenes knowledge that this guy’s back is bothering him, this guy’s shoulder hurts, the bullpen is short today, you need to get six innings from your starter because you don’t have the guys in the pen, stuff like that,” Cashman says. “There’s a whole bunch of information that as a fan you’d rather not know, because you’d rather just enjoy the game.”
Adjacent to Cashman’s box is the press box. Panels of dark glass separate the two, something Cashman says he had installed after stories began appearing about Steinbrenner paying him visits to yell at him. “It’s really about giving the Boss some privacy,” Cashman explains. “If Bill Gates wants to talk to one of his people at Microsoft, he doesn’t have to worry about it being in the papers the next day.”
Cashman discusses the Boss with both humor and sensitivity. He recalls the first time he drove Steinbrenner around as a young intern and hit a pothole on the FDR Drive. “This isn’t a freaking tank!” Steinbrenner yelled, not exactly in those words. At the same time, he disagrees with those who portray Steinbrenner as a backseat bully.
“He’s a worker,” Cashman says. “And he outworks everybody.” Steinbrenner has mellowed over the years, he adds, a sentiment shared by others in the Yankees’ organization. “He taught us a work ethic, we taught him patience,” Gene Michael avers.
Does Brian see himself working as Yankees GM for another nine seasons? Beyond? He shrugs. He thinks his relationship with the Boss is good, but doesn’t want to speak for Steinbrenner.
“I love baseball. I love what I’m doing. My preference is to stay.”
Torre says Cashman reminds him of Dal Maxvill, a longtime St. Louis Cardinal GM for whom Torre worked. “He’s the same type of personality, where they can be calm and collected but have a rough edge to them,” Torre says. “When they get angry, they let you know. There’s nothing Brian’s going to keep inside.”