Brian Cashman turns homeless for a night, sleeps outside for a cause

NEW YORK – Even though the temperature was in the high 30s, Brian Cashman thought it was colder as he stood in the dimly lit shadows of the World Trade Center on Thursday and heard the wind howling through canyons of city buildings. As soon as the Yankees’ general manager spread out his sleeping bag on a concrete plaza, he knew it was going to be a bad night.

This was the tenth year in a year and Cashman continues to do this. Every year he sleeps outside the Covenant House. This year, he joined over 260 individuals from the business, entertainment, and sports worlds to raise awareness and funding for the charity that combats adolescent homelessness.

Brian Cashman slept outside last night to raise awareness and funds for homeless youth through @CovenantHouse

(via @BryanHoch) pic.twitter.com/wBdmtzEp3Z

— Talkin’ Yanks (@TalkinYanks) November 18, 2022

Cashman told:

“It’s made a big difference. A night like tonight is a chance to hear from some of the success stories, who talk about what they’ve been through and where they are now. You can’t believe how smart and talented they are. All they needed was a chance to succeed and live a real life.”

As Cashman looked for a place to sleep near the corner of Barclay Street and West Broadway, he asked out loud how anyone could spend every night in such harsh conditions. Cashman has taken part in the Sleep Out at different places in New York City for more than 10 years. He has been in wind, rain, sleet, and snow. It never gets easier.

Last night, SVP & GM Brian Cashman participated in @CovenantHouse‘s Sleep Out for a night of solidarity and fundraising to support youth facing homelessness in New York City and throughout our country. pic.twitter.com/nxD4l0M21U

— New York Yankees (@Yankees) November 18, 2022

“I can tell you this: It’s called a Sleep Out, but there’ll be no sleep,” Cashman spoke, “My very first year was an eye-opening experience. I thought, ‘I’ll get some sleep — yeah, it’s on the street, but I’m in a sleeping bag.’ But you don’t get any sleep. Maybe it’s an hour or so. If you put yourself in somebody’s shoes like these kids we’re trying to help, they’re looking for a job. They’re looking for a way to survive … a place where they can get some sleep and be safe.”

As Cashman got ready for his restless night, he checked his pockets three times to make sure his cell phone was charged and there in case he had to use it overnight. Aaron Judge had just sent Cashman a text message in response to his congratulations on being named the Most Valuable Player in the American League. In the message, Judge thanked Cashman for his kind words.

Cashman said, “I was sure he was going to win, so I wanted to call him before I got here to congratulate him.” Judge recently met with managing general partner Hal Steinbrenner in person. From what everyone says, the meeting seems to have gone well. Cashman said that the Yankees have given Judge a new offer.

Meanwhile, Yankees fans, who often blasted Cashman on social media, admired his sleep-out for a cause.