Alphonse Gabriel (Scarface) Capone
Years: Lived 1899 - 1947. Ruled 1922 - 1931.
Who: Al Capone grew up to be a man who had the perfect job - have a gang in the murdering and bootlegging business and get paid for it. When prohibition started in the early 1920's, Capone was in Chicago, where he helped people who wanted booze. With moonshine machines, or just plain theft, Capone brewed the perfect drink to go with the people his gang killed. For almost a decade, Capone ruled the city, but he was caught. His crimes were so horrible, he was sentenced to the remote island's prison, Alcatraz, for 11 years. However, Capone suffered from syphilis, then had a stroke, ending his life with cardiac arrest. Capone is most famous for killing Bugs Moran, leader of the North Side Irish gang, an opposing gang of the "Capones" in the Saint Valentine's Day Massacre.
Weapons: Capone and his gang would bloody the streets with: Tommy Gun, M1918 BAR, Sawed Off Shotguns, Switchblades, Baseball Bats, Molotov Cocktails, Grenades, Pistols, and Revolvers.
Win or Lose: Probably set up, since Capone had a GRENADE rather a RIFLE, he lost in a 456 - 544 Kill Ratio against Jesse James. Although, he still had the deadliest weapon, the Tommy Gun, which obliterated the Wild West with 338 kills.