Willie Sharkey was a career criminal and enforcer who had known the Touhys from their days in the Valley. Sharky worked directly for "Chicken" McFadden. Nearly fifty-nine years old, Sharkey was short and pot-bellied like Roger, standing in at only five-feet, four-inches; he sported a four-inch horizontal scar on his left cheek and a two-inch scar on the corner of his right eyelid. Balding, he wore glasses and had a tattoo of a girl's head on his right elbow which winked when he moved his arm in a certain way.
The Touhys liked Sharkey's easygoing manner and good nature when he was sober, but otherwise they considered him dangerous, slightly insane and not very bright. (Law enforcement said he had the IQ of a child)
"Willie had two talents," Touhy said, "getting into jail and buying clothes that didn't fit him. He drank too much and he wasn't too smart, but he had a good heart and I liked him."
Sharkey's third talent was murder. At the time of the trip into the northwoods, Sharkey was wanted for questioning in Chicago in relation to at least five gangland slayings. In 1929 Willie and his brother John Sharkey, who played a role in several of the
Touhys' mail robberies, had opened a saloon just inside the Chicago line with an unknown partner. In 1931, the Capones kicked in the front door to the saloon and gunned down Sharkey's partner. "And since that time," John Sharkey told FBI agent Melvin Purvis, "I moved out of Chicago because of my relationship to my brother, and persons in the syndicate might endeavor to cause me trouble, such as killing me."
Willie Sharkey was a shy man who never married. However, he was proud of his brother and his family and supplemented their income with his own. Willie lived with them in Park Ridge for a while, giving his brother a Lincoln and a Ford.