Louis "Two Gun" Alterie (August 2, 1886 – July 18, 1935), born Leland A. Varain, and aka "Diamond Jack Alterie", was a Californian who became a notorious hitman for the Chicago North Side Gang during the early years of Prohibition. Early years Alterie was born Leland A. Varain in Northern California. He moved to Chicago as a young man, and eventually joined the predominantly Irish North Side Gang, which was headed by Dean O'Banion. Other prominent North Siders included Earl "Hymie" Weiss, Vincent "The Schemer" Drucci, and George "Bugs" Moran. Befitting his California background, Alterie was a Western enthusiast who wore a ten-gallon hat and two holstered Colt .45 revolvers and owned a ranch near Sedalia, Colorado. As well as being a top gunman for the North Side Gang, he also formed the Theatrical Janitors' Union and used his position as union president to extort money from theater owners. Gang war with Chicago Outfit In the early 1920s, the North Side Gang's greatest rival was the Chicago Outfit, run first by John "The Fox" Torrio and then Al Capone. During this period a series of disputes over bootlegging territories and other matters led the North Siders into conflict with the Outfit and its allies, the Genna brothers of Little Italy. Alterie by some reports killed more than 20 Outfit and Genna gang members during this conflict which had erupted into a full-scale gang war in 1924 when O'Banion was murdered by Outfit gunmen in his floral shop on State Street in Chicago. Exile to Colorado Alterie was considered the "flake" of the O'Banion gang. He once feigned insanity prior to a murder trial to give his criminal associates time to kill or intimidate witnesses. His act was so convincing that many considered him actually insane. Incensed by O'Banion's murder, Alterie publicly challenged his killers to a shootout on State Street. However, cooler heads within the North Side Gang were upset by Alterie's bravado; they worried that this would result in unwanted attention from both rival gangs and Chicago officials. Moran convinced Alterie to leave Chicago until it was safe to return. Alterie chose to go to his Moonridge ranch in Colorado. However, he soon attracted unwanted attention from the Colorado authorities. In November 1932, Alterie was involved in a gangland shooting in Glenwood Springs, Colorado. In February 1933, as part of a sentencing agreement, Alterie agreed to leave Colorado and