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It’s a quiet scene. A mounted party of Salish Indians have come across explorers on foot at what the Salish call the “Great Clearing” at Ross’ Hole in present-day Montana. Seeing that the newcomers have no buffalo robes, the natives proudly spread out three on the grass as an offering. After all, to their way of thinking, these white men must be mighty poor indeed not to own any buffalo robes. Yet the explorers turn them down, pointing to their own woolen blankets, a move that leaves the Indians stunned, probably even offended.

That September 4, 1809, meeting of the Flathead Nation and the famous expedition led by Meriwether Lewis and William Clark has been painted before—the legendary Charles M. Russell’s version for the Montana State Capitol, for example, comes quickly to mind—but Jesse W. Henderson gives it a fresh perspective, an Indian perspective, in his 4- by-7-foot oil on board. Henderson’s original painting was sold to a private collector, but his vision of Offering at the Great Clearing was chosen by the U.S. Postal Service to be reproduced on a “cachet”—a commemorative envelope first issued on May 14, 2004, at the Lewis and Clark Discovery Center in Great Falls, Mont., as part of the Lewis and Clark bicentennial celebration—and is also available in a limited edition of Giclée prints.

“I paint who I know, and I know Indians, I know horses, and I know cowboys,” says Henderson, a self-taught artist and member of Rocky Boy’s Chippewa-Cree tribe of Montana. “When I say Indians, I mean Northern Plains [Indians] and in particular Montana.”

Henderson, who now lives in Missoula, Mont., grew up on the Rocky Boy Reservation, learning all about horses and cattle while working on the family ranch in the Bear Paw Mountains. Talk about remote country. “You wouldn’t see anybody for months,” he says, “and if you saw anybody other than Indian people you knew they were lost.”

He grew up with a deep appreciation for the Indian way of life, and an equally deep love for cowboying. Nicknamed “Crazy Boy,” Henderson spent two years on the rodeo circuit, team roping and bareback riding, till a broken wrist sidelined his career. “You lived with pain,” he recalls. “I didn’t go to a doctor for months. When I finally did, the doctor said I had broken it. I said, ‘Well, fix it,’ and he said: ‘I can’t now. You waited too long.’” That left him contemplating his future, so he bought some paint. “It just fell out in canvas,” he admits.

“I can’t remember not doing it,” Henderson says of his love for painting. “I knew I had [talent], but I just screwed around with it.” Counsel from tribal elders eventually straightened out Crazy Boy. “They told me, ‘When the Great Spirit gives you that kind of talent,’” he recalls, “‘you need to share it. You’re recording our history.’ It didn’t take a whole lot of them to say that.”

So Henderson, who also works with watercolor and pencil and is beginning to sculpt, began entering fine-art competitions in 1998. Awards, honors and sales quickly came pouring in—first place, Western Heritage Art Association, 1999; featured artist, Helena Indian Art Market, 2003; best of classification & best of division, Heard Indian Market, 2004; selling out at the prestigious Santa Fe Indian Market in 2002 and winning a second-place ribbon there in 2004. His work has been displayed at the Heritage Gallery in Scottsdale, Ariz.; Lame Deer’s Indian Art Gallery in Big Bear, Calif.; Indian Uprising Gallery in Bozeman, Mont.; and the American Indian Art Center in Abilene, Kan.

Offering at the Great Clearing took eight months to complete. “The hardest part,” he says, “was putting it together, using journals and Flathead stories and putting it into a composite.” Although he’s known for “bucking the system,” Henderson insists on one thing: “Every painting I try to make authentic.”

In 2003 he began working on his Lewis and Clark series, all told from the Indian perspective. Another ongoing series portrays Montana Indian chiefs. Still, some subjects are off-limits. “Me? I can’t ever paint the scalp dance, not because someone says so, but because I respect it more than to have it sold as a commodity.”

A family man with a wife and two children, Henderson remains just a little bit crazy. He’s painting full time while his wife manages his business and runs Crazy Boy Consulting. He plans on keeping at it, and doing it Crazy Boy’s way. Case in point: He’s teaching himself to paint left-handed in case that old rodeo injury cripples his right hand. “I’m kind of cowboy, kind of great warrior culture,” he says. “People say, ‘Grow your hair long, shave off your mustache, take off your cowboy hat.’ No way. That’s who I am.”

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Originally published in the February 2006 issue of Wild West. To subscribe, click here.