December 2025
Magazine cover: Santa Claus, red suit, white beard, smiling.

Santa With a Purpose: Tom Bailey Turns Holiday Cheer into Generosity for His Community & Beyond

Much like the plot of the Disney classic The Santa Clause, Tom Bailey didn’t set out to be Santa Claus. But after 15 years of putting on the red suit and hat, perfecting his fluffy white beard and practicing his jolliest “ho, ho ho,” Tom takes on that title with pride, as he works to spread Christmas cheer to London and beyond.

 

Tom’s journey as Santa Claus began with a simple desire to bring happiness and festive spirit to his community. Tom quickly became a local favorite, but his reason for continuing to play Santa Claus year after year has changed in the last decade, as he spreads joy further than he ever imagined by donating most of his profits to a local missions program that provides resources to those less fortunate on the other side of the world.

 

Tom’s family moved to London when he was 13 years old, when he began attending church at Faith Assembly of God, where he met his now-wife, Karen, in the church youth choir. In 1977, the two got married when they were both 17 years old and, as Karen said, “the rest is history.”

 

Tom and Karen’s little family grew four years later with the birth of their first daughter, Misty. Later that same year, Karen was involved in a horrific car accident that left her severely injured and told she could never conceive again. Much to their surprise, Karen and Tom found out in 1989 that Karen was pregnant with their second child, their “miracle baby,” Kendra. And now, Tom and Karen have been blessed with five grandchildren to love.

 

Tom is now a retired truck driver; a career he took pride in for over 40 years. In addition to playing Santa Claus throughout the holiday season, Tom sings on the praise and worship team at the very same church he and Karen met all those years ago. Karen is a court reporter, which she has been doing for 32 years now. Karen also fulfills her “Mrs. Claus duties” by scheduling all of Tom’s events leading up to Christmas and running an extra suit to a photo shoot when Santa has sweat through his other one.

Tom began by playing Santa Claus in the church’s Christmas play at the request of his daughter, Misty.

 

“Because I always had my own padding,” Tom laughed. He would also dress up like Santa to take photos after the birth of their first grandchild.

 

Tom’s first real “Santa gig” took place at Modern Chic, a former local boutique, where he was asked to sit in on a photoshoot with shoppers. Tom said that in the first year, quite a few people showed up to take holiday photos, but by the following year, there was a line wrapped around the building.

 

“It was crazy, it was insane,” Tom said, recalling that soon another business owner was asking him to play Santa at their location, and before he knew it, Tom had an entire schedule of events lined up for the holiday season.

 

Now, 15 years later, Tom has become a local favorite during the holiday season, collaborating with local photographers and businesses, he visits schools and churches, he plays Santa Claus at holiday parties and even does some in-home visits. His reach has gone as far as Corbin, Barbourville and Clay County as of late.

 

Though he said he wasn’t looking for a side gig, a side gig had certainly found him. Tom was having to adjust his work schedule to accommodate his Santa schedule and running on very little sleep. Since his retirement in 2022, Tom has more time to dedicate to his Santa gig, starting events as early as the end of October and working up until a few days before Christmas. This year, Tom even participated in a Christmas in July event, the earliest he has ever done a Santa event so far.

 

Much like the big guy himself, Tom puts in long hours playing Santa Claus, often racing from one event to the next, though not in a sleigh being pulled by reindeer.


Even though his Santa gig takes Tom away from Karen a lot during the holiday season and usually means no making plans between the November and December months, she knows he is where he wants to be.

 

“I am happy to share him, because it really is his thing, he's in his element,” she said. “I am happy to fly solo during this holiday season if it means he’s bringing joy to kids in our community.”

 

When he first began playing Santa, Tom was wearing a fake beard, which he said was extremely itchy and uncomfortable. After two years of that, he decided he would try to grow his own beard, starting in August ahead of the holiday season and then starting in July the following year.

Santa Claus decorating a Christmas tree with red and gold ornaments in a well-lit living room.
Santa Claus sits in a chair with a woman beside him, in a room decorated for Christmas.

“It still wasn't to my satisfaction, so I backed up to June and she said, ‘you're killing me,’ because she hates this beard,” Tom teased his wife.

 

“So now he gives me until Mother’s Day,” Karen said, recalling how each year, at the end of the holiday season, Tom will shave off his signature Santa beard and waits until after Mother’s Day to start growing it back at the request of his wife.

 

Aside from the beard, Tom spends the months before the holiday season preparing by keeping up with the latest toy trends and making sure his Santa suits are all ready to go, while Karen helps to get his holiday schedule all lined out.

 

For Tom, one of the best parts about playing Santa Claus every year is seeing the joy on the faces of the kids he greets with a warm hug and a, “what do you want for Christmas this year?”

 

And it isn’t just about getting the perfect Facebook-worthy shot for Tom but about giving kids the real Santa Claus experience.

 

“I want to know their list, I want to know what's been going on, what grade they're in, how old they are, who their teacher is. ‘Do you have any puppies at home?’ I try to interact with them to loosen them up,” Tom said. “You want them to leave being happy. You’re going to have your little babies who are scared of Santa, but for the kids who want to have a good experience, I want them to leave saying, ‘OK, that may be the real Santa.’”

 

Through this experience, Tom has had a rare opportunity to see kids from all over the community grow up over the years; he has even had a few who were just children when they first visited him, and they are now bringing their own babies to visit Santa. One of Tom’s favorite parts is seeing them go from a shy kid who was too scared to talk to Santa one year to running straight into his arms by the next year.


And it isn’t just about getting the perfect Facebook-worthy shot for Tom but about giving kids the real Santa Claus experience.

 

“I want to know their list, I want to know what's been going on, what grade they're in, how old they are, who their teacher is. ‘Do you have any puppies at home?’ I try to interact with them to loosen them up,” Tom said. “You want them to leave being happy. You’re going to have your little babies who are scared of Santa, but for the kids who want to have a good experience, I want them to leave saying, ‘OK, that may be the real Santa.’”

 

Through this experience, Tom has had a rare opportunity to see kids from all over the community grow up over the years; he has even had a few who were just children when they first visited him, and they are now bringing their own babies to visit Santa. One of Tom’s favorite parts is seeing them go from a shy kid who was too scared to talk to Santa one year to running straight into his arms by the next year.

 

“Seeing a kid run up to me with their arms open for a big hug—I tell everybody, that is what keeps Santa's spirit alive,” Tom said.

 

Though it began to bring some joy during the holiday season and a little extra money for his family, the reason why Tom continues to put on the suit every year has changed a little in the last decade.

 

After a few years of him playing Santa Claus, Tom and Karen knew they wanted to make a meaningful impact with Tom’s holiday earnings and decided they would put that money towards a missions program through their church, called the Boys and Girls Missionary Challenge.

 

“They raise missions funds for missionaries overseas, different projects, and I've always supported that in a modest way because when you're working and you've got bills, you do what you can,” Tom said. “But one year we said we were going to take part of my proceeds from Santa and put it towards this program.”

 

Today, the Baileys put almost all the money Tom makes during the holiday season into this program.

 

Last year, the couple had an opportunity to see how their donations were making a difference as they visited Guatemala on a mission trip. But it was their trip to Africa earlier this year that made them look at things differently.

 

“It was life changing,” Karen said. There, Tom, Karen and others on the trip gifted families with much needed water filters. Tom and Karen were able to see that the donations they had been making for the last 10 years was helping to provide those water filters, making a huge difference in the lives of those living in places like Kenya.

 

“In America, we just can't imagine what it's like to not be able to run into the bathroom, turn your water on, wash your face, use water for cooking and all that,” Karen said. “I was overwhelmed immediately; I started crying because you could see that they were sick because they didn't have any clean water. You just don't realize the gift of water, what it means.

 

“It’s been such a game changer for us. He [Tom] has gone to a few photo shoots already this year and he'll bring home the money and it's like ‘this is $200—that's almost 10 water filters.’”

 

Before their trip to Africa, Tom had been considering stepping back from playing Santa Claus.

 

“I said I didn’t know how much longer I was going to be able to do this, and that was way before we went on the mission trip. But after I went on this mission trip, I came back and I said, ‘how can we not, how can I not do it?’”

 

“This mission trip changed everything,” Karen said. “We had already said, this is it—this year is it. And then we went to Africa, and it changed everything. As long as Tom is physically able to, he will continue to do it.”

 

As the Baileys continue their journey, their story serves as a powerful reminder of the difference we can make when we combine our passions with purpose. What began as a seasonal tradition has blossomed into a legacy of generosity and hope, touching lives across continents. Tom and Karen exemplify the true spirit of giving by not only transforming communities abroad but also inspiring those around them to see the extraordinary impact that compassion can have. Together, Tom and Karen find fulfillment in making a positive impact, one smile and one water filter at a time.

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