A look behind the red suit

Callan, a San Mateo-based Santa, started his career 20 years ago by accident. His daughter-in-law had a friend who worked in a department store where the Santa they hired did not show up. In desperate need to find a replacement, he was asked to fill in.

“I said, ‘Well, let’s see if the suit fits,’” Callan said. “I didn’t think much of it, but then one of the women came and talked to me there. Said, ‘By the way, we’ve got a Santa Claus scheduled to come to my day care center, and he just told me he’s going to retire instead. Could you come and be our Santa Claus?’ And I said, well, OK — I guess I could.”

After that gig, Callan continued receiving requests and invested in his very own suit. He would travel all over the Bay Area but would find himself overbooked and overworked.

“I was getting older and didn’t have to do so much,” Callan said. “I decided to cut back a little bit to the point where, this year, I’ve got almost all our returning customers.”

After shortening his travel, he would only make trips to homes in San Mateo. That was when he became San Mateo Santa and launched a website. Every week of Thanksgiving, his wife would hand wash his wig and beard in preparation for his upcoming bookings. Callan’s outfit consists of clothes, a wig, a beard and belly padding.

“They want Santa to be chubby,” Callan said in his bright red suit and beard white as snow. “There was a kid who said I wasn’t fat enough and I said, ‘That’s the nicest thing I ever heard. You want a jolly Santa with a belly full of jelly.’”

Family connections

When December arrives, the Santas become the stars of the season, and many families look to spice up their parties by inviting St. Nicolas himself. It not only makes it a memorable moment for families, but also for the Santas they invite into their homes.

“One family had me for 15 years,” Jim Callan said. “When she finally gave up, she said we gotta call this off. The kids are in college, and it was so emotional because we’d grown very attached. She gave me all kinds of advice early in my career.”  

Many times, Callan would leave events with his pockets full of letters from the kids to whom he had spoken.

Whether it be at your local mall, parties or events, there are men in red suits with years of experience who have different origin stories as to why they took the seasonal challenge to keep the belief of Santa alive.

“It’s a sense of responsibility every time I put this on,” Johnny Bayless, a Santa at Hillsdale Shopping Center, said. “It is a responsibility to show children and give them joy — to really try to make their dreams come true.”

This is Bayless’ sixth year as Santa at Hillsdale Shopping Center. From a young age, he knew he wanted to be Santa.

“My father told me that there wasn’t Santa Claus at a very early age,” Bayless said as he patiently waited for the line to see Santa fill up at Hillsdale. “I don’t know why. My parents had plenty of money, so that wasn’t the issue. But what it really did was make me want to be Santa — to show children that there’s something more than the mundane. It gave me a sense of desire.”

Real beards

Bayless, fully committed to being Santa, attended Santa School and joined FORBS, Fraternal Order of Real Bearded Santas. Every off-season, real bearded Santas who are part of the union attend monthly classes. Each class lasts about an hour.

“We did have to learn a lot about how to talk to the children and how to hold ourselves,” Bayless said. “There’s always something to learn. I wanted to be the best I can be at what I’m doing.”

This year, he discovered that the word “kids” is also used to refer to young goats. They are instructed to use terms like “children” or “boys and girls” instead.

Bayless’ beard has always been a defining part of his appearance. As both a musician and music instructor, it has remained a constant feature throughout his career. But for other Santas, the beard often requires preparation to complete the iconic look.

“I’ve been a real-bearded Santa Claus for about 10 years, but for the first 20 years, I was wearing a beard and wig,” said Owen Baker-Flynn, a Santa in San Francisco who grew into having a beard for the look.

Baker-Flynn made a friend with another Santa — Santa Glen — who recommended he grow out his beard.

“He said, ‘You should try it, grow a beard and see what happens, you know?’ And I did,” Baker-Flynn said. “I bleach it every year. It hurts and it burns, but it does make my life easier.”

Man of the hour

Baker-Flynn started his career as Santa in 1992. His 10-month-old daughter was about to experience her very first Christmas, and he planned for her to see Santa Claus. In an effort of trying to make this experience magical for her, he filled out a paper application and walked over to Emporium-Capwell in downtown San Francisco.

Santas are the man of the hour when December rolls around and the department store was having a hiring event looking for its star to complete their winter wonderland.

“They hired me and so my daughter came to see me as Santa Claus,” Baker-Flynn said.

Baker-Flynn was at Emporium-Capwell for three years until it closed and moved to Macy’s in Union Square. He didn’t quite enjoy his experience at Macy’s, so he decided to go freelance and join GigSalad, a website that connects people with local vendors and entertainers for their event needs. With many Santas posted on the website, job opportunities often fluctuate.

“Several of us are bidding on the same jobs but you don’t really see the competitive part,” Baker-Flynn said.

With 30 years of experience acting like Santa, Baker-Flynn feels motivated to continue after seeing his profit at the end of the season. Every five years, his wife makes him a new suit.

“She has made all my suits since I stopped going to Macy’s in the late ’90s,” Baker-Flynn said. “I can actually tell people Mrs. Claus made my suit. I have two right now, but I’ve had as many as four.”

When the demand for Santas slows down, he takes on roles as a high school baseball umpire, cartoonist and street performer — a career he has sustained for over 40 years at Pier 39.

“House parties are my favorite thing to do,” Baker-Flynn said. “I’ll talk to the parents beforehand. I’ll get a list of the kids who are going to be there. I’ll know something about them and bring this list with me. It makes it a very personal experience.”

Listening to children

The minute kids sit in Santa’s lap, it becomes a heartfelt moment for both of them as one listens and the other speaks of their desires.

“There’s something that happens to a person that puts on a suit and sits in a chair,” Desruisseau said. Children sat on my knee that whole day and blurted out all these honest little statements. Each one that you hear makes you even more endeared to the role. You hear things like, ‘I don’t want anything for me. I just want you to cure my mom’s cancer.’ Other children have lists that are as long as a roll of toilet paper.”

Desruisseau started his career out of a misunderstanding 40 years ago. In his 20s, he had a friend who had a photography business in Capitola. He had offered himself to help her take photos. He received a call from her to help her during a gig at a mall.

“I went to get to take photos,” Desruisseau said. “I got there and she’s like go in the back and change. Your outfit is there.”

Thinking there was going to be an elf costume, he opened the locker and to his surprise: It was a Santa suit.

“Begrudgingly, I got into the suit,” Desruisseau said.  

Inspired by the reactions he would receive and he took a trip to Disneyland, Desruisseau thought to himself, how can he bring entertainment to people’s homes? He saw performers acting like characters from the movies bring joy to families but he thought it was overpriced. He then started his own business, Albert Joseph Entertainment, 37 years ago.

His look as Santa is well kept by a professional stage makeup and hair stylist who styles it year-round for the perfect result. The outfits he wears are designed and hand sewn by a local seamstress.

“My suit is first class,” Desruisseau said. “It is a real leather belt with gold and silver in the buckle and real leather boots. Between the two of them, over $1,100 for just the belt and the boots.”

Gift giver

His goal is to embody St. Nicholas, the gift-giver of Myra, not only in his appearance but also in spirit, reflecting the same generosity in his actions. When he’s not playing Santa, he works as a caregiver. On his own time, he grows a garden and shares his produce with others. He has grown fondly of both jobs as they have given him an opportunity to spread love and joy.

“It’s the charming, endearing, unadulterated punch in the gut that some of these children deliver to me that keeps me coming back year after year,” Desruisseau said.

All of these Santas can be found on Gigsalad.com. More information about San Mateo Santa is available at SanMateoSanta.com.