By Steve Ulve
Journal contributor
People have always been attracted to Land’s End, where the archaic onslaught of the sea, weather and tides prescribe lifeways. Protein riches, freedom of movement and money schemes were relatively unconstrained. Even international borders were permeable at night or in the fog.
The past was gritty and colorful in these islands. Individual economic opportunity was good, risks great, while the only safety nets were caring neighbors. Stuart Island, an island somewhat apart from others in the archipelago, with a lighthouse at the sharp elbow of deep Haro Straight, good harbors, hardy homesteading families, mixed Coast Salish, contained valuable timber and fish. Personal tragedies lurked in the shadows.
A slight, friendly fellow, oddly named Little Wolf, claimed extraordinary life experiences back East, and may have first come to Stuart in the late 1920s. A lack of money, limited education, worn clothes, a limp and unusual stories were common during Prohibition. Yarnin’ and passing on knowledge were sociocultural activities.
Glenn “Little Wolf” Chester claimed Chippewa Indian blood and said that he broke out after years (and had suffered polio) in the Faribault Hospital for the Feeble Minded in Minnesota. Then at 19, he hopped boxcars to Chicago, where he somehow became a mechanic for Al Capone, the notorious bootlegger, and sometimes drove with “Scarface,” instructing from the back seat, bullets whizzing.
In about 1928, told to leave the island, he hoboed to Seattle, where he somehow hooked up with notorious ex-lawman turned whiskey smuggler, Roy Olmstead. Little Wolf claimed to operate speedboats, night-running booze from Canada to Smuggler’s Cove for the jailed Olmstead near the end of Prohibition. He spent decades in Seattle, mostly in shipyard plumbing and pipe-fitting.
He began fishing commercially, a career that lasted into the 1950s. Reliable information is scant. There are two softball interview articles in the Journal archives, circa 1980, and some paragraphs in local books. Settling in the 1960s, Little Wolf happily welcomed visitors to his Reid Harbor shack with stories, fried bacon, maybe a nip or two. He kept two dogs, numerous fowl, a cat and flew a wolf’s head flag. Favoring grease-fried beefsteak or eggs, shunning vegetables, he worked hard as so many did, at nearby reef-net sites. Paul Harvey’s radio show, “The rest of the story,” was a favorite. He caroused in Friday Harbor bars.
There are photos in the tiny Stuart Museum. In the shaded cemetery, Little Wolf’s headstone is embedded with a signature copper wire bracelet. Perhaps you know Stuart or hail from pioneer and native families who dwelt there, or know of the loose-knit hippy enclave in the 1970s? Stories of place.
But Little Wolf’s most far-fetched tale, frequently retold, was that at five, he and his younger sister were abandoned in the deep woods by an evil babysitter. He remembered acceptance and regurgitated feeding by wolves with pups. Clothes rotting, they were eventually discovered by hunters who shot the wolves, bagged, then caged the feisty, grubby kids, making money showing them (or selling them to a circus). Eventually, do-gooders intervened to make him a ward of the state in 1913. Oddly, his parents never surfaced. He never learned of his sister’s fate. He had original paperwork from that institution bearing the name Glenn Chester, born 1908. Islanders helped him claim social security, easing his life until the Health Department recorded his death on May 9, 1984. Little Wolf was 75 and had created a lasting legend.
