Distinctly Montana Magazine

D I S T I N C T L Y M O N T A N A M A G A Z I N E • F A L L 2 0 2 1 94 THE BOOTLEGGING LADY OF GLACIER PARK Of all the lady bootleggers, we know the most about Jo- sephine Doody. John Fraley interviewed people Josephine knew and shared her story in his book, Wild River Pioneers: Adventures in the Middle Fork of the Flathead, Great Bear Wilderness, and Glacier National Park. And we have photos of her that are part of the Glacier National Park Archives. Georgia-born Josephine Gaines traveled to Colorado. The story gets sketchy but suffice it to say, a dead man and Josephine's smoking gun made her a fugitive. She fled to Montana, landing work in a dancehall in McCarthyville—a long-gone railroad town near Marias Pass. Dan Doody, a pa- tron, fell in love with Josephine and stole her away via mule to his remote cabin near Glacier Park. She had no choice but to kick her opium habit and, in time, embraced their lifestyle—hunting, fishing, and guiding big game hunters. Josephine had a knack for making moonshine and evading the law. Dan was friends with James J. Hill, a founder of the Great Northern Railroad that passed their homestead. Hill liked to fish and hunt with Dan and offered to have the train stop whenever Dan or Josephine needed a ride. This became a convenient way of getting their moonshine into rail work- ers' hands, who distributed it to customers along the way. Railroad workers blew the train's whistle, one toot for each quart. They had a booming business. Josephine outlived Dan by 15 years and continued boot- legging. She proudly wore large gold nugget earrings that had stretched her earlobes like bananas, her friend Rick "Tiny" Powell said. The nugget earrings disappeared when she died, but her posthumous portrait by Roundup artist Jane Stanfel will always show her proudly wearing her trea- sured jewelry. BERTIE'S FAMOUS MOONSHINE Stanfel also paid tribute to another prominent bootlegger, Bertie (Birdie) Brown. Stanfel, whose artwork graces walls in galleries, museums, and homes in the U.S. and abroad, painted Bertie's homestead in Fergus County. Bertie moved to Montana in 1891 and became one of the first Black wom- en to homestead independently in the state. Her good nature, tidy "home speak" and famously good moonshine meant she had a steady stream of patrons. Ru- mor has it she plied Lewistown's Officer Hill with liquor to let her off with just a warning to shut down her bootlegging business. After that warning, Bertie was dry cleaning with gasoline and cooking what would be her last batch of moon- shine. It exploded, and she died from her burns. A TWO-TIME WIDOW Like Bertie, Mathilda Wallace was a homesteader. Her nature wasn't as genial, though. Ken Robison, an author and historian at Fort Benton's Overholser Historical Research Center, wrote about "Tillie." Seems she married a man twice her age when she was just 17. She became a widow at 33. Bad luck? I'm not so sure. She made her way to Montana with her daughter, home- steading near Square Butte. There she met James Line- barger. Locals suspected she poisoned this common-law husband, but she was never charged. Tillie hung onto the homestead by bootlegging until revenuers confiscated her still and whiskey. With no source of extra income, she even- tually sold the land for $10 and was never seen again. BEATING THE RAP Few women bootleggers spent time behind bars. Of those who were caught, most received a warning or fine. Jails weren't equipped to have women inmates or their children. Butte widow Annie O'Day was caught with 250 gallons of mash. She fled to California with her four children. The Montana judge dropped all charges on one condition: An- nie would forever stay in San Francisco. Some women were flat-out too mean to go to jail. Mrs. Steve Gregovich greeted Sheriff Mahoney at the door with a pitchfork, said she'd use it on him, and was never approached again about the bootlegging business she ran from her kitchen. Though she did pay a fine for making 905 gallons of grappa—well over the 200 gallons allotted per year for a household. The incoming freight cars loaded with crates of grapes were hard for lawmen to ignore. Josephine and Bertie's brews were more discreet. They used local crops and fresh mountain water. Texas-based Saint Liberty Whiskey honors these two bootleggers with Bertie's Bear Gulch Whiskey and Josephine's Flathead

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