The Great Train Robbery, 1963
This neatly executed caper began two hours before dawn on Aug. 8, 1963, just as Royal Mail train conductor Jack Mills noticed a red signal where one shouldn't have been. After Mills stopped the train to investigate, he was confronted by 15 men clad in ski masks and helmets. In less than 15 minutes, the men had emptied the train of 124 mail sacks carrying $7,145,600 in bank notes, many of them old bills destined to be taken out of circulation. Just 120 miles away from the scene of the crime sat the robber's hideaway, Leatherslade Farm in Buckinghamshire, England, where they counted the cash and later used it to play a game of Monopoly. But the bandits failed to execute the cleanup as smartly as they had the crime, doing such a poor job at torching the farmhouse that police found everyone's fingerprints, including some on the Monopoly board.
Twelve of the 15 men were captured and arrested, including one Ronnie Biggs, who engineered his own jail break in 1965 and later spent almost a decade hopping continents and going under the knife to avoid being caught by police. Scotland Yard investigator Jack Slipper found a much-altered Biggs in Brazil in 1974 and greeted him by saying, "Long time no see, Ronnie!" But much to Slipper's chagrin, Brazilian authorities refused to extradite Biggs; he finally surrendered to British police in 2001.