Surf Cowboy: Craig Cunningham

If you were a male in my family, you were a cowboy, or a bronco rider, or you were left behind,” says Craig Cunningham, saddle-maker, surf instructor, artist, and lifetime cowboy. “As a youngster those were the kind of people I was surrounded by. My grandfathers and uncles were my heroes, and I wanted to be like them.”

Craig, who repairs and builds custom saddles and other gear from his Kailua-Kona workshop, was born into a multi-generational ranching family in South Dakota. Raised on the range, Craig says that’s what spurred his saddle-making career.

“It started with my relatives, and me getting broken stuff and hand-me-downs as a kid,” says Craig. “My grandfather, uncles, and dad were watching me; they wanted to see my reactions. I was one of those kids who was naturally curious. I would tear it up and figure it out and fix it. The more desire and interest I showed, the more knowledge they shared.”

One of those uncles, Casey Tibbs, was a nine-time Professional Rodeo Cowboys Association champion in the 40s and 50s. He was a columnist for Rodeo Sports News, starred in numerous movies and worked as a professional stuntman. In 1973, Casey introduced rodeo to Japan, according to CaseyTibbs.com. A Foundation and Rodeo Center in South Dakota continues to promote the sport of rodeo and the cowboy heritage in his name.

“Guys who are good are not going to waste their time on people who don’t care,” says Craig. “If you are an honest human being, there will be doors that open. For artists, craftsmen, it’s the same way. It was trial and error learning as a kid. If it gets broke, you’ve got to pull it apart and try to fix it. It changed who I was as a cowboy. They would say, ‘He’s a boy. Let’s make him a man. Step up. There’s no reason you can’t learn.’ It helped build my work ethic.”

The family moved to California when Craig was about eight, and he fell in love with the ocean. “I was always in the water anyhow. If there was a pond, lake, crick or stream around, I was in it,” says Craig.

“By junior high school, I was a young cattleman,” he says. “I used to ride with my uncles, and one of them would say, ‘See that cow over there? Can you tell what’s wrong with her?’ ”

This kind of on-the-job training taught him a great deal in a short time. “My grandfather would go into town to drink coffee and eat a doughnut, and he’d say to his buddies, ‘Ask Craig what kind of bull you should crossbreed…’ and I’d go on and on and on.”

Craig attended Kansas State University and studied Ranch Operations Management. He worked on ranches across the western states and competed in rodeo, including Cheyenne Frontier Days and the Calgary Stampede, although he never focused on rodeo as a career.

“In college, learning technical aspects made me into kind of a well-rounded cowboy deluxe,” says Craig. “Once I got to where I couldn’t really cowboy that much, I decided to devote more time to my craft.” His journey continued to top saddle making schools, Montana Saddle School in Belgrade, and Jesse Smith in Colorado.

At one point, while he was recovering from a rodeo injury, a friend invited him to come to Hawai‘i, where he was going to work for Parker Ranch. Craig enjoyed some sun and surf, and not long after, moved to the North Shore of O‘ahu for a few years, then came to Hawai‘i Island.

“I love the ocean so much and the ranching culture so much,” says Craig. “This is the perfect place for me to be. It’s a blessing.”

He started out in the small workshop at Pukalani Stables in Waimea, repairing saddles, bridles and other gear, building custom saddles and various small items. He and wife Susie, an avid surfer, embraced the Hawaiian culture, learned as much as they could, and chose the name Kua‘āina Saddlery for their business. After a lot of research and consideration, Kua‘āina, “back country,” seemed a good fit for them and for their work.

Craig says it took a few years for people to trust him completely and to count on the fact that he was not going to leave. “I was in Waimea four years and got deeper and deeper and deeper into the family history.” (See Dr. Berginʻs story here.)

“Dr. Bergin was my go-to guy,” says Craig. “He introduced me to all the right people, he helped make me successful. He pushed me towards the working cowboy genre and helped me build business on the coconut wireless [word-of-mouth],” he says. “I know what it’s like when you only make this much money—it’s hard to make repairs. I let them pay it off over time, and it worked really well. Everyone seemed happy.”

Craig says that even as his reputation grew, saddle work is sporadic in Hawai‘i. The majority of his work goes to the mainland and other countries, and he might only build one saddle in a year. For that reason, he diversified into making unique gift items such as wallets, purses, knife sheaths, dog collars, custom motorcycle seats, tank bibs and more. Their new custom leather sleeves for water bottles and Hydro Flasks with handles are in-demand.

He works with care, taking time to twist his own horsehair rope, braid rawhide, make cinches and fine-tune the details that make for quality products that last. Many elements of Hawaiian culture are evident in Craig’s designs: florals, petroglyphs, woven lauhala patterns, waves, and geometric shapes evocative of ‘ohe kāpala (bamboo stamps).

He’s also found time to branch out, working construction, becoming a certified lifeguard, surfing instructor, artist, musician, and cowboy poet. He and Susie (who’s also a surf instructor) have seven children, in what Craig calls a “Brady Bunch” style blended family. Grown up now, the family includes a professional team roper, bronco rider, cowboy surfer, security guard, girls longboard champ with Hawaii Amateur Surf Association, and a successful Registered Nurse at Queens Hospital.

“It’s been a blessing with my kids. Some are into ranching, some ocean, but we all fit together somehow,” Craig says. “And Susie, she’s the power behind the throne, so to speak. I could not be successful without her.”

Most recently, Craig has started working on a series of color pencil/pen and ink drawings that feature traditional Japanese full-body tattoos. The designs feature koi, dragons, lotus, and clouds swept together in water patterns and reflections.

“I’ve taken them to a Japanese tattoo artist who said, ‘For a haole boy, this detail is amazing. It brings something from your own mind into Japanese body art. Ho, bra’, that’s sick…’ And that’s where I get gratification. I need money to pay bills, but this is where I get my fulfillment—the wow.” ❖

Contact Craig Cunningham, 808.345.4642

Contact writer and photographer Catherine Tarleton