A Minnesota bootlegger's son delves into his father's lawless past

Shortly before he died, Robert Wilson shook his head when his son tried to calm him by saying they'd meet again in heaven.

"He told me he'd done too many bad things," said Winston Wilson, 80, a retired machinist from Coon Rapids. "I'd heard stories but never really knew anything until after he passed."

The youngest of five siblings who grew up in Minneapolis, Winston knew his dad as a hard-working, anti-union truck driver who hauled dirt, excavated and dabbled in construction north of the Twin Cities.

"I never saw my dad cry or heard him say, 'I love you,' although I knew he did," Winston said. "Things were different. They thought they had to be manly."

After his father died at 86 in 1989, Winston started scouring microfilm of Depression-era newspapers. They told of a car-stealing bootlegger who led cops on a high-speed, gun-popping chase, who vowed never to be taken alive but ultimately wound up in the federal prison in Leavenworth, Kan.

"There are so many questions I wished I would have asked," Winston said.

The eighth child of a farm family from the central Wisconsin town of Plainfield, Robert Wilson was born in 1903. He never got past third grade, stole cars as a teenager and smoked unfiltered Camels, his son said.

Wilson was too young to fight in the First World War and too old for World War II, but the Depression hit while he was in his 30s. "They had no money and bootlegging was a way to survive," Winston said.

Wilson began frustrating police in 1935 when, according to newspaper accounts, he brandished a rifle to escape arrest. That summer he was nearly nabbed while driving on 6th Street near Hennepin Avenue in downtown Minneapolis, fleeing after pushing a federal marshal from his car with a gun.

"The swashbuckling suspect," as the Minneapolis Tribune described him, again escaped in May 1936 during "a wild chase and gunfight" through south Minneapolis. Zooming through city streets at 80 mph, police shot out a tire on Wilson's car at 66th Street and Cedar Avenue. He abandoned the car and exchanged gunfire with police, disappearing in the darkness and leaving behind his wife, Loretta, and 5-year-old daughter, Donna.

Wilson failed to fulfill his never-be-taken-alive pledge when five federal agents and two Minneapolis detectives burst into his bedroom at 2720 3rd Av. S. just after 2 a.m. on a Saturday in July 1936. One account said he was "cowering in a clothes closet," while another said he was in bed at the time. He surrendered without a struggle.

Wilson pleaded not guilty to charges of operating a distillery in Columbia Heights and possessing alcohol. He insisted he'd been working odd jobs, not bootlegging, and explained that the new car seized by police agents had been "bought on a finance plan."

But he was sentenced to five years in Leavenworth and fined $3,000. "My mother and their four older children all moved to Leavenworth to be near him," said Winston, who was born two years after his father — having served about 3½ years —was released from prison in 1940.

Robert Wilson turned his life around. By 1950, he was back in Minneapolis with Loretta and the three kids still at home, working construction and driving a truck. Winston said his dad even gave up the unfiltered Camels — cold turkey — in 1960.

"He had a farm near Spooner [Wis,] and I worked with him for a while, hauling dirt to produce farms and excavating," Winston said. "Like the World War II guys who never told their families what they'd seen, my dad didn't say much about the trouble he got into."

Winston's photo album includes a circa 1918 photo of his father as a teenager, hat in hand and dressed in a suit and knickers. There's a family portrait from 1945, showing Robert, Loretta and their five kids — including Robert Jr. in his Navy uniform and 3-year-old Winston in a matching sailor suit.

"My father was never a drinker," Winston said. "In my whole life, I probably saw him drink a couple beers and never finish the whole bottle. My mother once said he had a friend check to see if the moonshine was any good."

Loretta died in 1979, a decade before her husband, and both were laid to rest at Twitchell Cemetery in Lino Lakes. Their daughter Donna joined them at the cemetery in 1992 — shortly after she went with Winston to the Minneapolis Central Library to scan the old newspaper accounts of their father's lawless youth.

"I didn't dig in as a younger man," Winston said. "And I wish I had because there's so much I'd like to ask my dad."

Curt Brown's tales about Minnesota's history appear each Sunday. Readers can send him ideas and suggestions at mnhistory@startribune.com. His latest book looks at 1918 Minnesota, when flu, war and fires converged: strib.mn/MN1918.