‘I DON’T LOOK DOWN’
Yankees GM rappels down Stamford’s tallest building in annual tradition
STAMFORD — At the top of the Landmark Building, Yankees General Manager Brian Cashman sat straddled over the building’s ledge. While one of his feet dangled hundreds of feet in the air, he laughed and chattered with Fox News meteorologist Adam Klotz.
Considering the longtime sports executive’s enduring reputation as an adrenaline junkie, Cashman’s annual descent down Stamford’s tallest building is unsurprising.
“I don’t look down ever, still,” he said to a gaggle of cameras early Friday morning.
Cashman on Sunday at 5 p.m. will rappel again down the building as part of Stamford’s annual Heights and Lights spectacular. For the 54year-old manager, it marks the 11th year he stars in one of the city’s strangest holiday rituals.
Cashman, who lives in Darien, will settle into his familiar role as a holiday elf, joined by a cast of wintertime characters played by Stamford residents. Following the 350-foot descent, he will zip-line to the Ferguson Library, followed by a fireworks display.
The last stop in the festive yuletide trek will take Cashman to Latham Park for the city’s annual tree lighting and carols from the Yuletide Singers. Admission to all these events is free of charge.
Stamford Downtown, in its many iterations, has been flinging people off the Landmark Building since 1984. The inaugural event was part promotion, part fundraiser for Connecticut-based nonprofit Save the Children. A local rock-climbing instructor dressed in a Santa costume stuffed with a single pillow descended for the first rappel.
As it goes with most events that straddle the line between enthralling and uncanny, rappelling Santa became a staple of Stamford’s holiday repertoire.
Cashman joined Heights and Lights after the Yankees’ World Series win in 2009.
“I was invited to watch the rappel from Zaza,” a restaurant with a fronton view of the Landmark Building, he said. After a few cocktails, watching the display unfold from the front window and surrounded by family, he made a crack about wanting to try rappelling the next year.
Stamford Downtown Vice President Lynne Colatrella held him to it the following year.
While Klotz played partner to Cashman this year for the practice run, there’s been a revolving door of other participants over the decadeplus of rappels.
Stamford’s hometown legend and recent mayoral candidate Bobby Valentine joined Cashman in 2013 and 2019 for the descent. 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 along with Cashman.
Aside from the big names, the Santa rappel 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 staff Heights and Lights form bonds as well.
“Everyone here has played a role and everyone comes back and does it again,” Long Ridge Fire Company Chief Dan Dauplaise said while watching Cashman prep for another trip down the building. The fire company helps manage the 230-foot rope that hangs off the building, according to Dauplaise, who holds a seat on the Board of Education.
Stamford police officer Heather Franc is another standard participant in the holiday rappel. She’s played Mrs. Claus a handful of times; it’s gotten to the point where she can coolly sip a coffee while standing at the top of the Landmark Building while watching the preparations unfold.
“It’s just fun,” she remarked matter-of-factually, unperturbed by the aerial theatrics to come.
Fun and thrills, the holidays and community: What else can you ask for?