People & Place
  • Montana Art - Gerald's Cowboy Boots - Whitefish Gallery

In the Northwest reaches of Montana, in the one-time stump-town known as Whitefish, there lives a man known well for his flamboyant collection of boots, hats and other custom-tailored Western clothing, and yet, very few know the story of Cowboy Gerald, his boots, his past or his purpose. 

A story awaits to be told in all of us. For some it’s a little closer to the surface than others. For Cowboy Gerald, it’s perhaps hidden behind the fine custom-made apparels, which are worn daily. It wasn’t until I sat down with the Cowboy, following a casual compliment, “That’s a fine pair of boots you have on” that he pushed a chair away from the table with his boot and said with a grin, “Sit down and I’ll tell you about them”. 

In a matter of minutes, I knew there was much more to the man behind the boots than just a colorful collector…

Cowboy Gerald never met a stranger. And yet the man well known for his flamboyant boot collection is a mystery to many. 

This is the story of a man about town whose dress adds color to an already colorful landscape and who inspires a smile from persons already content with the offerings of life; a man whose custom-designed boots, while fascinating, intricate and wild in nature perhaps best tell his story — a man who is content to live out his days in our quaint little town as he presses toward the goal, intent on finishing well. 


The Making of the Cowboy

Gerald Daymude was born on June 22, 1938, in Washington, D.C. He lived in the suburb of Kensington, Maryland, just 15 minutes from the district line. He worked for his father who was a mechanical contractor — plumbing, heating, welding, etc. After a few years the company swelled to 65 men, all working to build Washington, D.C., and thriving areas. 

Gerald worked for 50 cents per hour for his dad and eventually saved enough money to purchase his first pair of “real boots” at the age of 10. “In 1948 I bought my first pair of boots for 40 bucks, I think. We all wore engineering boots, but I wanted a pair like the cowboys wore in the films,” Gerald said. 

It wasn’t until the late ‘60s that Cowboy Gerald adopted his western attire. After retiring, Gerald moved out West and worked as a missionary in a few states spreading the Gospel to mostly Native American tribes. 

“I was called away from home to do missionary work,” recalls Gerald. “I worked with the Navaho Indians around Flagstaff, Arizona, for almost six years. I was in charge of maintenance—we had seven churches and the headquarters. I kept everything working right. That was a good job. If I hadn’t got hurt, I’d probably still be out there,” Gerald added. 

The “hurt” Gerald refers to is a mystery ailment the locals call “Navaho Mystery Disease” which is believed to be passed on by deer mice commonly found on the reservation. 

“I couldn’t no longer put my arms above my head,” says Gerald. Gerald had used his talents to help renovate the churches on the reservation and it is believed that this is where he contracted the sickness. “I started having shortness of breath, and after my lungs collapsed twice, I knew my missionary work was over.” 


A New Life, A New Man

Gerald left Flagstaff in 2000 to take care of his mother who passed away shortly after his return. After his mother passed, Gerald traveled in search of a new home. In early 2003 Gerald made his way into Whitefish. “I sat there on that bench,” he said pointing to one of the benches lining the downtown street, “and just watched people and listened. These people (referring to the Whitefish locals) are so friendly here. They just made me feel so warm and welcome,” Gerald said with the excitement of a young boy. “When I found my apartment, things just came together naturally.” 

Shortly thereafter, Gerald returned home to make arrangements with the movers and came to Whitefish with only the necessities: his bible, his boots and hats, his tea kettles and pictures of his family. “I got everything a man could ever need here. I got a church, a roof over my head, a comfortable bed, and now I got some really good friends,” Gerald said, his eyes beginning to tear.  

Gerald has established a real sense of community during his past two years in Whitefish — one most would hope to achieve in their lifetime. 

“I eat breakfast every mornin’ at the Buffalo Café, then I enjoy a cup of coffee at Montana Coffee Traders. The folks there are always so nice to me and a lot of folks (customers) talk to me about my boots,” Gerald said, smiling. “I spend a couple hours walking around town doin’ some tradin’ and such, and then usually wind up at Mrs. Spoonover’s (Ice Cream Parlor) at the end of the day for a cup of soup.” 

Mrs. Spoonovers’s is a local’s favorite hang-out neighboring The Back Door General Store where some of Cowboy Gerald’s fine boots are on display. Gerald introduces Trini, the store’s owner as his “best friend.” Trini (who also sells real estate through the Montana Land Office) looks out for Gerald and often takes him on tours of new listings as a way of helping Gerald to get out and see the surrounding area. 

“We have so many people come into our shop after meeting Gerald on the street to ask him about his boots. He tells them he has some on display at our shop and in they walk. He’s really like a spokesperson for our business.” Trini adds. 


These Boots are Made…

Now what about those boots? Since buying his first pair of boots at the age of 10, Gerald has steadily amassed a collection of nearly 60 boots, many of which were custom-made by some of the most famous boot-makers of our time and have been featured in books and magazines around the world. 

While some of the boots are actually made from vintage designs which Gerald has commissioned, most of the boots are his personal designs, each with a story and purpose and individual inspiration.

Most all the boots start off with the same basic criteria, a 16-inch top, a cupped 4-inch heal and the outline of Gerald’s 7 _ E foot. 

“I send them designs that I sketch or sometimes pictures of vintage boots I find in books and such, then give ‘em special instructions, like how many stitches I want, colors and so on. Most boot makers won’t do more than 10 rows of stitches (referring to the stitches that outline or make up the design) but I got one pair made by Paul Bond that has 25 rows of stitches. Boot collectors can’t believe I got 25 rows!” Gerald says with a big smile, holding up a pair of boots. 

Gerald is right; most boot collectors have never seen a pair of boots with more than 18 rows of stitches, let alone 25 stitches done by world-renowned (and now retired) Paul Bond. 

Gerald never wears the same pair of boots two days in a row to keep them fresh and to keep the townspeople guessing. Though, around the Christmas Season, Gerald may wear the pair with Christmas trees on them several times in one week. 

Gerald also owns a fine collection of hats, many of which were also custom-made. And during the winter months wears a “blanket coat” which was also custom-made for him by the talented tailor, Kathy French of Columbia Falls (Montana). 

“I bought that blanket and brought it to Kathy and asked her to make me one of them coats. When she gave me the finished coat a few weeks later I just couldn’t believe it. She said she looked at that blanket for three days before she figured out where to cut it,” Gerald said, buttoning up his jacket. 


Conversation Pieces

While researching this story, my wife and I were fortunate to spend a good deal of time with Cowboy Gerald and after each encounter, we walked away asking or learning more about ourselves and the current direction of our own lives. 

In the end, Cowboy Gerald’s story is one of inspiration. He teaches us that we can come from nothing or nowhere, and despite personal hardships, ailments or age, we can always forge a new life and new relationships if we’re simply willing to step out in faith. We feel blessed to have met him and to call him a friend.  

Independent sources estimate the value of Gerald’s boot collection in the hundreds of thousands — perhaps making it the most valuable non-vintage boot collection in the world. 

When asked of their value, Gerald responded by saying, “they’re worth a good conversation every time—you can’t put a dollar figure on that.” 



Special Thanks to Tracy Eastman of the Whitefish Free Press for helping with the interview and to Bob and Cindy for allowing us to use their ranch for the photo shoot.  

Source Info: Blanket Coat: Kathy French, Columbia Falls, MT (406) 892-5736

Book: Cowboy Boots by Tyler Beard.


~ Clint Walker works out of Whitefish, contributing writing and photography to magazines worldwide. Many of his images are available as limited edition prints through his website at