Photo at left: Ford Moretz, 2, of Darien, sized up Santa (a.k.a., William Armstrong Jr. of Westport) with wide-eyed wonder during an encounter at Stew Leonard’s market in Norwalk. Right: Chloe Serna, 10, of Norwalk, posed with Santa to please her mom’s request. / Photos by Gretchen Webster
Photo at left: Vinny Condito, of Norwalk, talked football with Santa after he noticed Condito’s Cleveland Browns-logo sweatshirt. Right: Home for the holidays, Westporters Cooper Tirola, left, and friend Ben Seideman, right, accompanied Cooper’s grandmother, Barbara Tirola, to Stew Leonard’s where they were greeted by Santa. Both young men are 2023 graduates of Staples High School and now college freshmen — Cooper at Miami University of Ohio and Ben at Indiana University.

By Gretchen Webster

WESTPORT — He’s a substitute teacher at Staples High School. A public relations writer. A former writer for the U.S. secretary of the Interior and the Republican National Committee. And more. 

But from the day after every Thanksgiving until Christmas, William Armstrong Jr. is something else entirely.

He’s Santa Claus.

Megan Armellimi gave Santa an exuberant “high five” during a recent visit to Stew Leonard’s, with her children, Addie, 3, and Lily, 1.

Every day after he leaves Staples and on weekends, the Westport resident drives (by car, the reindeer are in reserve for Christmas Eve) to Stew Leonard’s grocery store in Norwalk, where he dons the traditional red suit and hat accented with white “fur.” Armstrong doesn’t need a fake beard — his snowy white beard is all his own.

At the busy market he meets, greets and poses with people of all ages, from newborns in strollers to the elderly in wheelchairs. “It’s nice to see you again,” he says to every adult that he speaks to, brimming with good cheer.

Armstrong has learned greetings in many different languages to make the people and children he meets feel at ease, no matter where they are from. “Santa is a universal symbol,” he said.

“I want them to leave with a happy thought, that’s the goal in the end,” he said on a recent day at the store. “It’s just fun to play that part and get a bit of good will from each of them.”

Armstrong takes his role as Santa very seriously, responding to each person, no matter what the age, in a way he believes will make them feel happy and safe. Tiny babies look at him wide eyed, not old enough to be afraid as some toddlers may be. For those a little older, he holds out one finger, and they touch a finger to his, which often turns their look of fear into a smile.

He completely understands why children may be frightened of a strange man with a big beard, “a wild furry suit and bells on the wrist,” so he does his best to dispel any fear.

Photo at left: August Gonzalez, 20 months, of Westport, with mom, Andi, was a little uncertain about meeting a man with a big white beard and a bright red suit. Right: Lee Bowen, of Stamford, shared a laugh with Santa when he asked her to leave out food for him during his Christmas Eve visit.
Santa heard Christmas wishes from Andrew Ferson, 4, of Westport, as his mother, Caroline, looked on.

He jokes with adults, telling them to leave out food for him on Christmas Eve, or when noticing a sweatshirt with a team logo, a sports chat follows. A woman pushing a grocery cart tells him, “You make a very believable Santa,” prompting Armstrong to respond, “You make a very believable shopper.”

His Santa job at Stew Leonard’s started unexpectedly five years ago when the store’s human resources director handed him an application to portray Santa Claus as he was shopping. “She liked my demeanor and attitude — and the whiskers helped a lot,” he said.

And he continues to enjoy playing the role. A member of the Connecticut Society of Santas, he also has portrayed Old St. Nick at several charitable events arranged by the group at Circle of Care, a nonprofit group in Wilton supporting children with cancer.

Armstrong has also made a few Santa “house calls” for friends and his three grandchildren, who are 4 and 1 years old and 4 months old. But he doesn’t take on the “gig work,” he says, that many Santas in the society do, traveling to events around the region. He works full time as a Staples substitute teacher, and besides, he likes returning to Stew’s, where he sees many of the same children year after year.

“There are kids I’ve held at 6 weeks old, and I see them every year for four or five years,” he said. “It’s fun to see them grow up.”

When he first took on the job, he had to figure out what it meant to portray such a universally known character. Part of it is finding ways for people to respond to Santa Claus, as well as to give children and adults and incentive to do good and be kind to each other.

“You can’t ever contaminate that brand,” he said. “It’s a very important trust that is placed in anybody that is cast in this role.”

Santa’s last day at Stew Leonard’s this year was Friday.

After that, he said, “I have to go back and pack my sleigh.”

Freelance writer Gretchen Webster, a Fairfield County journalist and journalism teacher for many years, was editor of the Fairfield Minuteman newspaper for 10 years and teaches journalism at Southern Connecticut State University.

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