Where I Live: Windcrest

The Where I Live series aims to showcase our diverse city and region by spotlighting its many vibrant neighborhoods. Each week a local resident invites us over and lets us in on what makes their neighborhood special. Have we been to your neighborhood yet? Get in touch to share your story.

This commentary was originally published in 2020, when Jim Flinn was in his 16th year as Windcrest’s Santa Jim. Due to the pandemic, he had to put his annual open house tradition on hold, but he and his neighbors made sure to keep the magic of Windcrest alive with plenty of lights and holiday decorations.

This year, things are back in full swing and Flinn said over 500 guests stopped by for his 2023 open house. His 2020 commentary is below.

When my wife, Karen, and I were growing up in Miami, one of our neighbors would go all out decorating his home for the holidays. He didn’t just hang up a string of lights and call it a day like most people; every year he would create a true winter wonderland.

His garage would open up and a sleigh would come out onto his driveway. He even gave out presents to the kids in the neighborhood. I remember thinking, “That’s what I want to be when I grow up.” 

After 30 years in the Army, I retired in the perfect place to live out that childhood dream. Just outside of San Antonio, Windcrest has a small-town charm and love for the holidays that makes me feel right at home. Here I can go overboard with my Christmas decorations without the neighbors thinking I’m too much. I fit right in.

When I retired, I started letting my beard grow out and it started going salt-and-pepper — until it became more salt than pepper. A friend who was a music teacher at a local elementary school asked me to fill in when their Santa for the school’s Breakfast with Santa fundraiser got sick one year. I agreed and got bitten by the bug. Now I’m in my 16th year as Santa Jim.

As part of a group called Lone Star Santas, it’s important to me to not only spread Christmas cheer but to also give back to the community. Our Convoy of Toys provides gifts to children affected by natural disasters, and it’s an initiative we’re very proud of.

In addition to attending private and corporate parties, I usually go out to Morgan’s Wonderland and Ronald McDonald House. My wife and I also have our own open house for one night in December. As people visit the city to see the holiday lights, we invite them in off the street for a free photo with Santa.

As the tradition grew, we added cocoa and cookies, carolers in the yard and toys for the children. We have a guestbook that we ask visitors to sign, and it’s amazing how many people from all over the country and the world travel to the area for the holidays. One year we had over 900 people come through the house. This year, due to the pandemic, we have to put this tradition on hold, but we look forward to resuming when it’s safe to do so.

The annual light-up ceremony is what Windcrest is known for and marks one of my favorite days of the year. The fire department comes to the house to pick Mr. and Mrs. Claus up, and we drive through the city and up to City Hall. Just about everyone in town will be gathered out front waiting for the lighting of the Christmas tree. When I arrive, the sound of Christmas music and the crowd’s anticipation instantly put me in a good mood. I go up and say a few words, then we do a countdown and flip the switch. When the tree lights up, it’s a magical moment. 

Last year was the first year the City of Windcrest dedicated a portion of Windway Drive to me: Santa Jim’s Candy Cane Lane. For one month of the year, I have a street named after me. It’s such an honor to have that recognition, but I have to give credit to everyone in Windcrest — especially the city employees who work so hard every year — for making the holiday season memorable.

Of course, being the Windcrest Santa and being involved in our city’s holiday festivities, I get to know a lot of the neighbors and residents of Windcrest. I feel like I have an important role to play in this community and that I’m part of everyone’s family.

I’ve been stationed in different places around the country, and it’s always the small towns that draw me in. In small, tight-knit communities, it’s easier to get to know your neighbors and there’s a sense of security in knowing that we all look out for one another.

When you’re in a big city you’re often so focused on getting from point A to point B that you aren’t looking at anything in between. When you drive through our city, you notice the ranch-style homes shaded by big oak trees, which is what first drew me to Windcrest. I like to say that in Windcrest we don’t have a lot of sky because it’s blocked by our beautiful oak trees. It’s nice on a hot summer day to have three-quarters of your yard in the shade.

And it’s nice to slow down once in a while. We’re so often in a hurry and forget to look around, forget to just enjoy where we are. Windcrest forces you to slow down (the speed limit on most streets is 20 miles per hour) and allows you to enjoy the journey.