Cashman is scheduled to rappel from the 350-foot Landmark Building in Stamford, Conn., Friday and Sunday as part of the Stamford's Heights and Lights event as a celebrity guest elf.
Wearing a full harness and dressed in an elf costume, according to Stamford Downtown president Sandy Goldstein, Cashman will jump off the 22-floor building. There is no protective netting, a spokesperson for the event said.
"I've been leaving milk and cookies for Santa for some time now, but this year I wanted to take a more active role in assisting him," Cashman said. "As an elf, you have to be willing to build toys, wrap presents, prepare reindeer for flight, or rappel off buildings for Santa. I take my role as an elf seriously because there are a lot of children out there counting on him."
This past week, Goldstein asked Cashman if he was scared.
"Sandy, nothing is scarier than general managing the Yankees," Cashman said, according to Goldstein.
Cashman, who lives in nearby Darien, volunteered to take part after witnessing the event last year.
"He indicated he would be really interested doing it so we followed up," Goldstein said.
He will have a rehearsal Friday morning that will be aired on Fox 5 in New York. On Sunday, Cashman will jump off the ledge at 4:30 p.m. ET in the actual event.
"Brian is a spunky guy who scuba dives and plays baseball," Goldstein said. "This is a new career. This is his maiden flight off a building."
Goldstein said she wasn't sure if Cashman would don the full elf costume for rehearsal in front of the cameras Friday, but he certainly will Sunday, she said.
"He certainly is going to be dressed as an elf," Goldstein said. "This is a magical moment."
Goldstein said that Cashman will come down with Santa Claus and, after 15 years of the event, she knows you have to be tough-minded to do it.
"You are in a harness and you have to step off of the roof of a 22 stories-high building," Goldstein said. "I wouldn't do it for all the tea in China. This is not for the faint. You really have to be macho to do this."
After the jump, Cashman will leave for the winter meetings, which start Monday in Orlando.
Andrew Marchand covers baseball for ESPNNewYork.com.