A night on the street teaches Yankees GM life lessons

A groggy Brian Cashman spent a restless night of sleep on a New York sidewalk, in the interest of charity.
A groggy Brian Cashman spent a restless night of sleep on a New York sidewalk, in the interest of charity.Stan Grossfeld/Globe Staff

NEW YORK — It's 5 a.m., and Yankees general manager Brian Cashman is unshaven and lying in a sleeping bag spread over a soggy U-Haul box on the wet concrete just off 10th Avenue. His voice is nearly drowned out by the sound of semis grunting their way toward the mouth of the nearby Lincoln Tunnel.

"I am a cranky Yankee," says Cashman, dressed in a camouflage baseball cap, gray T-shirt, and rain pants. "I couldn't fall asleep. I've got a knot in my neck. I need a shower. It was a nasty night."

Cashman was among 200 business leaders who spent a recent night on the concrete as part of the Covenant House's "Sleep Out" event to raise money and awareness for the plight of homeless children. He wound up getting a total of 90 minutes' sleep.


"No dreams. No REM," says Cashman, who has participated in "Sleep Out" the last five years. Cashman's friend from Catholic University, Kevin Ryan, is Covenant House president, and Cashman is on its board of directors.

"The first year, I literally got no sleep," says Cashman. "Zero. I was a zombie for a day-and-a-half recovery time. It was a nightmare."

For this year's "Sleep Out," there were 1,000 participants in 15 other cities across the US and Canada. The volunteers raised $1.5 million in New York, $6 million total. Worldwide, the organization assists 51,000 children a year in 27 cities across six countries.

Upstairs on this November night, 400 children and young adults slept safely in Covenant House.

Downstairs, Cashman tossed and turned but refused to go inside.

"Half the people don't know who he is, and he doesn't care," says Joseph Vitale, a State Senator from New Jersey who also slept out. "Brian has an enormously stressful job and very little time. He could just write a check but instead he walks the walk and raises money."


"He's not looking for fanfare; he really wants to make a difference, he'll do anything to help," says Jim White, the executive director of Covenant House of New Jersey, who once had Cashman sing "Meet The Mets" to raise money.

Shattering stereotypes

When Cashman arrived in the early evening, he was fielding a phone call from another general manager as he pulled into the parking garage.

"I said I'm open for business all night," says Cashman. "I think any general manager in the game is open 24/7 if a good idea comes their way."

Cashman checks his cellphone every few minutes all night long.

"You know, I'm like a teenager — you can't put the thing down," he says.

Yankees general manager Brian Cashman during the Covenant House’s “Sleep Out” event.
Yankees general manager Brian Cashman during the Covenant House’s “Sleep Out” event.Stan Grossfeld/Globe Staff

The evening begins with seminars with Covenant House graduates, before the executives take to the streets. This will be the only time Cashman puts his phone away.

He listens intently as Hannah, an abuse survivor who had lived on the streets since she was 13, says her biggest surprise was that Covenant House serves three meals a day.

"I thought that only happened in the movies," says Hannah, who has a 4.0 grade point average at a local college while working at a special needs residence.

Other survivors talk about having birthday cakes for the first time in their lives.

"You don't know if the air blows out the candles or it's the tears," says one counselor.

Cashman says "Sleep Out" helps to dash the stereotypes the public has about homeless youth.


"I think people have an assumption that you're there because you directed your life that way," he says. "You get what you reap, almost like you deserve this.

"But they are smart, passionate, and hungry. They've just been dealt a bad set of cards at the front end of their lives.

"The only difference between them and me is they don't have any sponsors."

Cashman, 48, got a job with the Yankees as a 19-year-old college intern. His father, who managed a horse racing track in Florida, was friends with Yankees owner George Steinbrenner. When Steinbrenner was suspended by Major League Baseball, general manager Gene Michael took over, and he promoted Cashman to assistant GM in 1992. Cashman became GM six years later.

Since then, he has won six American League pennants and four World Series. But he wears no rings.

"That's not my style," he says. "They're in safes."

Known to be different

The wiry Cashman is a former Division 3 second baseman. He's also fearless, once rappelling down a 22-floor Stamford, Conn., building dressed as an elf at Christmas and jumping with the Army parachute team the Golden Knights to raise money and awareness for the Wounded Warriors program. His first jump, from Homestead, Fla., was so much fun that Cashman went again. He broke his foot and underwent two surgeries.

"I've got a plate with 8 screws in my right ankle," he says. "Do I regret it? No, it was wild."


He's also brutally honest, once telling Alex Rodriguez to "shut the [expletive] up," when A-Rod tweeted that his surgeon had cleared him to play before he had been examined by Yankees doctors.

He regrets the A-Rod comment.

"I just erupted," says Cashman. "And normally I don't erupt. I lost my cool."

But nearly everyone liked it.

"Probably, yeah," he says, "but I try to be professional, and that's not professional."

He reportedly told Yankee icon Derek Jeter during 2010 contract negotiations that he would prefer Troy Tulowitzki at shortstop

"I've got a good relationship with Derek — at least I think I do — but I have no regrets on being honest and direct when asked to be,'' says Cashman.

Even a sleep-deprived Cashman wasn't looking to deal with the Red Sox. Asked if he would be interested in Pablo Sandoval and Hanley Ramirez, two high-priced and so far disappointing Sox acquisitions, Cashman smiles and says, "We're not looking to add more money."

At the trade deadline last season, he tried to obtain All-Star closer Craig Kimbrel, whom the Sox recently acquired from the San Diego Padres for prospects.

"He's a great player," says Cashman. "They have a very deep farm system that they traded from, and they acquired one of the best closers in baseball. So they gave a lot, but they got a lot."

Don't expect him to trade with new Red Sox president of baseball operations Dave Dombrowski any time soon. In 1999, Dombrowski, then general manager of the Marlins, sent three minor league pitchers to the Yankees in exchange for a promising third baseman named Mike Lowell.


"He got my head on a scalpel on that one trade that I wish I could have back," says Cashman.

He said the Yankees will not ignore the David Ortiz Farewell Tour when it rumbles into the Bronx next season.

"The Red Sox have always been really, really classy," says Cashman. "Everything they've ever done. I have a great deal of respect for how they've done their business."

The days of the "Evil Empire" references are over, he says.

"No one brings that up anymore," says Cashman. "Boston is my favorite city to go to. The fans are amazing and the rivalry is amazing. They may hate the Yankees, but they respect that we're trying to win just like we respect they're trying to win."

But what about the vulgar chants that still can be heard in the stands at Fenway Park?

"I lived in the city for a long time and car alarms have gone off and you actually get numb to it," says Cashman. "The chant, I don't even hear it anymore."

A lesson in perspective

During the night, the temperature was in the 50s, so Cashman was warm. But the cellphone was cold.

You can never have enough starting pitching, he says — "They are like racehorses, they can go down at anytime and normally they do" — but the lessons learned sleeping on the street help put things in perspective in life.

When Yankees pitcher CC Sabathia announced Oct. 5 he would enter alcohol rehab — the day before the Yankees lost to the Houston Astros in the American League wild-card game — Cashman took it in stride.

"There was only one course of action, which was full-court support in any way, shape, or form," he says. "The game and our professional team efforts were clearly secondary."

Cashman wipes his eyes and stands up. At 5:15 a.m., rush-hour traffic is already starting, and Cashman has to drive to his Connecticut home and work on rosters.

"What do I learn from this?" he says. "This is real life. In baseball, you give it your best effort and then you get to go home, win or lose."

This Thanksgiving, he has a lot to be thankful for.

"I'm the luckiest guy," says Cashman. "You walk away with an amazing appreciation of the abilities and upsides that these kids have."

Stan Grossfeld can be reached at grossfeld@globe.com.