From his arrival in Canada to his death, Picariello was a larger-than-life personality. In 1899, at the age of 20, he immigrated to the United States. He came to Toronto in 1902 and arrived in Fernie in 1911. He was a loving husband to Maria and proud father of their six children. A successful entrepreneur, he operated a number of businesses, beginning in eastern Canada and culminating in Fernie and Blairmore. He served as a one-term town councillor. To the poor and to friends, he was generous.
Picariello became a bootlegger operating between Fernie in British Columbia and Blairmore and Lethbridge in Alberta, as well as in the American Pacific Northwest. As one of the so-called “criminal class” of bootleggers for whom this was a business, he became a target for the Alberta Provincial Police.
On September 21, 1922, the A.P.P. and local police set up a sting operation in Coleman and Blairmore to entrap Picariello and his men while engaged in a bootlegging run. Chased by the police, Picariello’s son Steve was shot in the hand by A.P.P. Constable Stephen Oldacres Lawson. Picariello, accompanied by a young family friend, Florence Lassandro, confronted Lawson about his son’s condition later that evening at the A.P.P. detachment in Coleman, and Lawson was shot.