September's selection is a news article about Giacomo "Big Jim" Colosimo, who is credited as the first mob boss of the Chicago Outfit. Born in Italy in 1878, Colosimo emigrated to Chicago in 1895. He began working as a pimp at the age of 18, and is known for having engaged in Black Hand extortion practices, an old Italian racketeering scheme where he would anonymously send threatening letters to those with outstanding debts and signing them with a handprint in black ink. His prostitution and racketeering practices were put to use when he was recruited to work as a bagman for two of the First Ward's Democratic aldermen, saloonkeeper Michael Kenna and bathhouse owner John Coughlin. This business arrangement with Chicago Democrats helped propel him to his eventual wealth, where he was able to control the majority of Chicago's prostitution business with an estimated 200 brothels. His wife, Victoria Moresco, solicited the help from her nephew, Johnny Torrio, from New York after Colosimo was threatened with Black Hand letters from extortionists who had taken notice of his wealth. Torrio shot and killed the three bagmen as they came to pick up his money, and from that point on became Colosimo's apprentice. When Torrio moved to Chicago, he brought with him one of his top New York lieutenants: Al Capone. Colosimo and Torrio's relationship declined after Colosimo divorced Torrio's aunt for a 19-year old singer named Dale Winter, who frequently sang at Colosimo's Café located on 2126 S. Wabash Ave. Colosimo and Torrio also held conflicting business attitudes once Prohibition started in 1920. Torrio wanted to try to smuggle rye whiskey from Canada and cut out the middle man, while Colosimo felt that doing so would garner too much attention. After overruling Torrio on the matter, Colosimo was shot and killed at his Café. The original suspects included his ex-wife, Victoria, or his current wife, Dale Winter. The waiter working at the Café that day identified Frankie Yale out of a lineup, but did not end up testifying against him, which later resulted in prosecutors dropping Yale's case. Al Capone allegedly confessed to having murdered Colosimo to a mob-connected reporter, but nothing was ever substantiated. The attached article further details the murder and those suspected of killing the Outfit's first mob boss.