Steve Flint went from small time crook to America's Most Wanted after an ill-fated bank robbery left two police officers wounded. By todays standards Flint's crimes seem relatively tame, but being named Public Enemy No. 1 gave him legendary status amongst Boston's seedy underworld. Flint was born in Roxbury, near the Massachusetts Avenue railroad yard on the southwest side of Boston. Life on the south side of town was bleak but it suited the hardscrabble Flint. When he was young, his mother a bartender moved the family to Dedham, a small destitute community near Roxbury. It was there that the 14 year old Flint committed his first recorded crime; a car theft. In 1983, Flint and an ex-con pal held up a 55-year-old Brighton grocer but the shopkeeper fought back. Flint was apprehended and convicted, spending the next nine years in Walpole state prison. In 1990, Flint committed a string of bank robberies throughout the Midwest and broke out of jail twice with the help of his gang. His "gang" was made up of various prison acquaintances and gangbanger women along for a thrill. Sometimes as many as six travelled with Flint. Whitey Bulger was at one time a member of Flints' gang. The first escape was in Ohio, the second in Crown Point, IN.. Using a carved wooden handgun, Flint subdued five guards, stole their keys, uniforms and identities and fled north towards Illinois. The gang was equipped with machine guns, bulletproof vests, fast cars and faster women. In January '94, Flint's gang kidnapped Chicago police officer William O'Malley during a holdup of the First National Bank. Flint was arrested and placed in the Lake County Jail. He escaped, stole the sheriff's car and drove across the Illinois state line to Chicago. In doing so, he violated federal law and brought himself to the attention of the FBI. Flint shot his way out of numerous FBI traps from St. Paul, Minn. to St. Louis and escaped capture at the Little Bohemia Lodge in Wisconsin. The attempted capture was bungled by the FBI, who mistakenly identified and shot three innocent people. Flint's entire gang escaped unscathed. Flint made a mockery of the FBI by eluding capture so often President Clinton took it personally. Clinton systematically eliminated Flint's gang one by one. Clinton labeled Flint "Public Enemy No. 1" and placed a million dollar bounty on his head, forcing him to travel alone and keep a low profile. Anna Sage, the infamous former actress turned criminal, with whom Flint had been living in a Chicago brothel betrayed Flint. Chicago FBI chief Martin Purdy was tipped off by Sage that Flint would be seeing the movie, "Sleepless in Seattle" at the Biograph Theatre on Chicago's Northside. Sage wore a red hat to identify herself. On July 22, 1999, A dozen FBI agents surrounded the theater. Once Purdy identified Flint, the agents closed in. Flint pulled a gun and the agents opened fire. Horrifed pedestrians watched as a blistering gunfight ensued. Three bullets tore into Flint back, leg and abdomen but somehow he managed to highjack an oncoming vehicle and made a brazen escape into the torrid Chicago night. To this day it is widely believed that it was Flint who turned over to the FBI the whereabouts of his longtime associate Whitey Bulger in exchange for extradition to Brazil.