NEW YORK -- The temperature was in the high 30s, but it seemed colder on Thursday as Brian Cashman stood in the dimly lit shadows of the World Trade Center, hearing the wind howl through canyons of city structures. Unrolling a sleeping bag in a concrete plaza, the Yankees' general manager immediately knew he was in for an awful night.

That’s the point, of course, which is why Cashman continues to grit his teeth, don a ski cap and put on an extra pair of socks every year for the Covenant House Sleep Out. He joined more than 260 leaders from the business, entertainment and sports industries to raise awareness and funds for the organization, which combats youth homelessness.

“It’s been a real difference-maker,” Cashman said. “A night like tonight, it’s a chance to hear from some of the success stories, who share what they’ve been through and where they are now. You’re just blown away by how amazingly gifted they are. All they needed was a chance to succeed and have a real life.”

As Cashman searched for a suitable sleeping location near the corners of Barclay Street and West Broadway, he wondered aloud how anyone could be subjected to these raw conditions, night after night. Over more than 10 years of participating in the Sleep Out at various New York City locations, Cashman has experienced wind, rain, sleet and snow. It never gets easier.

“I can tell you this: It’s called a Sleep Out, but there’ll be no sleep,” Cashman said. “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 prepared for his restless evening, he triple-checked his pockets, ensuring that his cell phone was charged and present in the event of overnight business. A text message from Aaron Judge had just arrived, a reply to thank Cashman for his congratulations on winning the American League Most Valuable Player Award.

“I wanted to call him before I got down here to congratulate him because I was like, ‘There’s no way he’s not winning it,’” Cashman said. “But then I was like, ‘Well, I don’t want to be a jinx.’ It was well-deserved. What an amazing season. Clearly, we hope his Yankee career isn’t over yet. It’s an amazing moment for him, his family and the Yankee organization.”

Judge recently had a face-to-face meeting with managing general partner Hal Steinbrenner that, by all accounts, seems to have gone well. Cashman confirmed that the Yankees have made an updated offer to Judge, who turned down a seven-year, $213.5 million extension before Opening Day.

“It’s in real time, so we’re on the clock,” Cashman said. “We’re certainly not going to mess around. We’ve made another offer since Spring Training.”

Even so, Judge is looking forward to testing the free-agent market, with the slugger noting that his tour of interested suitors could extend into the Dec. 4-7 Winter Meetings in San Diego.

“I don’t think there’s any more pressure on us than there already is,” Cashman said. “Whether he won the award or not, he’s been our team leader and our best player. We definitely feel the pressure, and rightfully so. He bet on himself this spring, and it really paid off. That can go a lot of different ways, but he made sure it went nothing but north.”

While the Yankees hope that Judge will be the centerpiece of their offseason rebuild, Steinbrenner has placed more on the agenda. First baseman Anthony Rizzo returned this week on a two-year pact worth at least $40 million, and Cashman said that the club would be in the mix for other trade possibilities and free-agent pursuits.

“We will be in play with trying to improve our team in other aspects, without a doubt -- not just Rizzo and not just our attempt to sign Judge,” Cashman said. “Obviously, [Steinbrenner] wants to put a team that is capable of taking a shot at a World Series title on the field. It’d be perfect if we can deal with all of that this winter.”