Yankees GM Brian Cashman Prepares For Annual Holiday Rappel

STAMFORD, CT — Brian Cashman is no stranger to stressful situations. After all, he has been the General Manager of the New York Yankees for over two decades.

So on a chilly Friday morning, Cashman practiced rappelling down the side of the 22-story Landmark Building in downtown Stamford for the annual Heights & Lights event, which is scheduled for Sunday, Dec. 5.

The event is sponsored by Reckson and put on by the Stamford Downtown Special Services District. Attendance is free and open to the public.

Ar 5 p.m. on Sunday, Cashman and friends — Santa Claus, Rudolph and the Grinch — will make their daredevil descent down the side of the Landmark Building, and then zip-line to the Ferguson Library where there will be fireworks.

Afterwards, Santa will head up Bedford Street to Latham Park and join the Stamford community for holiday music and the lighting of the holiday tree.

Cashman, who admittedly is afraid of heights, is participating in his 11th rappel. He said the trick is to not look down.

"The first three years were terrifying, but now it's pretty routine. We have a great safety team, and over the course of time you learn how everything works so you start to intuitively trust everything," he told Patch Friday after a practice run.

Adam Klotz, a meteorologist from Fox News, joined Cashman on a rappel for an appearance on the morning show "Fox & Friends".

The event was closed to the public in 2020 due to the COVID-19 pandemic, but with lower case numbers and vaccinations now widespread, a crowd will be allowed to attend on Sunday.

Cashman said he's excited to see a live audience again.

"I think that this Sunday night we have a chance to have a big turnout. I can't stress enough that this is a great family event. It's what attracted me when I first moved into the Fairfield County area," Cashman said.

Fresh off a World Series win in 2009, Cashman was given the opportunity to watch the rappel with his children from ZAZA, the Italian restaurant located across the street from the Landmark Building.

"I had a table for dinner, we were inside so we weren't cold and we had a front row seat," Cashman recalled. "I had a few cocktails flowing, and I said, 'Man, it would be so cool to do that.'"

David Kooris, president of Stamford Downtown, said Cashman helps elevate the annual event "to a different regional level."

Every year, people from New York, New Jersey and elsewhere in Connecticut come for the holiday festivities.

"It's commensurate with our position as a real regional center," Kooris added. "There are all kinds of holiday and winter stuff, but it's pretty rare and unique for people to get to see their favorite holiday characters going down the side of a massive building. Seeing that moment of surprise, it's definitely what does it for me."

Kooris, too, is excited to see a live audience once again on Sunday, but he said it's still "an odd time" with the pandemic lingering.

"We're still trying to make decisions on a day-to-day basis. The ground is ever-shifting beneath us, but I think we've gotten a really good response from the community. We're doing our best," he said.

Normally during this time, Cashman is busy trying to make moves and put together a team for the next season.

But with a lockout and work stoppage implemented this week because of the expired Collective Bargaining Agreement between team owners and the Major League Baseball Players Association, contract negotiations and roster moves are prohibited.

The Yankees, who have one of the highest payrolls in baseball, have largely sat out on this offseason's loaded free agent class so far. Fans have been outspoken on social media.

When asked what his message is to Yankees fans, Cashman said he couldn't comment on anything related to Major League operations as a result of the lockout, and instead referred to the MLB Commissioner's Office.