Cashman will be among 40 sports, business and entertainment leaders assisting the Covenant House Crisis Shelter, hoping to raise awareness and funds to help homeless children.
"Nobody is obviously trying to compare one night of sleeping in the streets to what a homeless child goes through," Cashman said. "But the effort here is to try to raise up to a half million dollars to benefit the programs as we move forward."
Cashman is a member of Covenant House's board of directors and has been active in the program's efforts.
Following a candlelight vigil in Times Square and a performance by musician Natalie Grant, the participants will sleep outside on the concrete behind the Covenant House New York Crisis Shelter at 460 West 41st Street.
"These are leaders who have selflessly decided they want to walk in our kids' shoes, and experience, if only for one night, some of what our kids go through," said Covenant House president Kevin Ryan.
"I've had the chance to meet some pretty inspiring kids who are fighting for a lot," Cashman said. "They're fighting homelessness and they've obviously had a curveball thrown their way, and in many cases, not by their own fault. They're trying to fight to emerge from that, and Covenant House has been pretty spectacular.
"The one thing we say is, 'Homeless does not mean hopeless.' Clearly, it's a great organization."