“I never look down”

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STAMFORD — Atop the Landmark Building, Yankees general manager Brian Cashman sat astride the ledge of the building. As one of his feet dangled hundreds of feet in the air, he laughed and chatted with Fox News weatherman Adam Klotz.

Given the longtime sports executive’s enduring reputation as an adrenaline junkie, Cashman’s annual descent into Stamford’s tallest building comes as no surprise.

“I never look down, always,” he told a group of cameras early Friday morning.

Cashman on Sunday at 5 p.m. will rappel down the building again as part of Stamford’s annual Heights and Lights show. For the 54-year-old manager, this is the 11th year he has played in one of the weirdest holiday rituals in town.

Cashman, who lives in Darien, will settle into his familiar role as the holiday elf, joined by a cast of wintry characters played by locals from Stamford. After the 350-foot descent, it will zipline to the Ferguson Library, followed by a fireworks display.


The final leg of the festive Christmas ride will take Cashman to Latham Park for the town’s annual tree lighting and caroling by the Yuletide Singers. Admission to all of these events is free.

Stamford Downtown, in its many iterations, has driven people out of the Landmark Building since 1984. The inaugural event was both a promotion and fundraiser for Save the Children, a Connecticut-based nonprofit. A local climbing instructor in a single-pillow-stuffed Santa costume came down for the first abseil.

As with most events that straddle the line between exciting and weird, Santa’s encore has become a staple of Stamford’s holiday repertoire.

Cashman joined Heights and Lights after the Yankees won the World Series in 2009.

“I was invited to watch the encore of Zaza,” a restaurant with a front view of the Landmark Building, he said. After a few cocktails, watching the show unfold from the front window and surrounded by his family, he fancied trying abseiling next year.

Stamford Downtown Vice President Lynne Colatrella retained him the following year.

While Klotz played Cashman’s partner this year for the practice run, there has been a revolving door of other entrants over the decade and more callbacks.

Stamford hometown legend and recent mayoral candidate Bobby Valentine joined Cashman in 2013 and 2019 for the downhill. One year, Jose Feliciano – the Weston resident and Puerto Rican singer famous for “Feliz Navidad” – performed his holiday standard during the celebration. For the 2020 edition, Yankees manager Aaron Boone scaled the building with Cashman.

Apart from big names, the reminder of Santa Claus has also become a point of unity among community members. There are the crowds of spectators, of course, but the people who come back year after year to animate Heights and Lights also create ties.

“Everyone here played a part and everyone comes back and does it again,” Long Ridge Fire Company chief Dan Dauplaise said, watching Cashman prepare for another trip through the building. The fire company is helping manage the 230-foot rope that hangs from the building, according to Dauplaise, who sits on the school board.

Another standard participant in the holiday recall is Stamford Police Officer Heather Frank. She played Mrs. Claus a handful of times; it’s gotten to the point where she can quietly sip coffee while standing atop the Landmark Building while watching the preparations unfold.

“It’s just fun,” she remarked evenly, unfazed by the air theater to come.

Fun and thrills, holidays and community: what more could you ask for?

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