"The very first time I ever did this, I could not operate the next day," Cashman said. "I had a sleeping bag and they give you a slab of cardboard to sleep on. I got no hours of sleep that night. I don't know how anybody gets up and has to do this every day and try to decide where to lay their head at night, feel like they're safe, actually get any sleep."
Cashman, who serves on Covenant House's board of directors, said that he will keep his mobile phone in action on Thursday evening, continuing his 24/7 availability in discussions to improve the Yankees' on-field product. He said that it is even possible something could be completed before sunrise.
"I think there are some things in play that if some teams say yea to the positions I've taken, then yeah," Cashman said. "There's been some time that's developed between the last deal and the current status, but I can honestly tell you I was on the phone with a general manager as I was pulling in to the parking garage, so you never know."
Cashman met the organization's future president, Kevin Ryan, while they were students at the Catholic University of America. Audra McDonald, a six-time Tony Award winner, also participated in Thursday's candlelight vigil and Sleep Out, which aimed to raise $6 million to benefit those in need.
"No one is saying sleeping out for one night is comparable to what homeless kids go through," Ryan said. "But our vigil and our Sleep Out will raise awareness and funds needed to save the lives of kids who are right now living and dying on our streets. It will be a powerful night of hope for our kids."
In past years, Cashman said he bundled up in ski gear, which provided layers of cushion against the unforgiving concrete. Mother Nature tossed a curveball on Thursday, offering warmer temperatures in the mid-60s but pounding rainfall.
"This will be a challenge tonight, more than any other ones, because of the rain," Cashman said.
The most meaningful part of the annual event, to Cashman, has been having the opportunity to meet with some of the individuals that Covenant House has helped over the years.
"They have so much potential, so much opportunity," Cashman said. "They were just dealt a bad hand on the front end of their lives. A place like this, the personnel working it are really doing tremendous work to put them in a better position to get along with a life and build a life."