Of all the quirky schemes dreamed up in war time, the raid organized by Lieutenant Bennett Young takes the cake. A Kentucky calvary officer during the Civil War, Bennett received a commission from the Confederacy to stage raids from Canada to rob Union banks to line the South’s coffers. His one and only action was the successful raid of Saint Albans , in which he and 20 other cavalrymen galloped the 15 miles from the Canadian border and took over the town on October 19, 1864, herding the panicked townsfolk onto the village green and simultaneously robbing three banks.
The soldiers made off with some $200,000, though their celebration was cut short when they were captured in Montreal a few weeks later and forced to give back some $90,000 they still had on them. Despite the best efforts of the United States, however, neutral Canada refused to extradite the soldiers, saying they were acting under official orders, and Young and his confederates were never tried for their offenses.
As a postscript, the incident was made into a mildly successful movie, The Raid, in 1954, in which the Bennett Young character played by Van Heflin comes to St. Albans  weeks before the raid and falls in love with a pretty townswoman played by Anne Bancroft. Needless to say, that part is heavily fictionalized.