Robbery on the Rails

As the train slowed down on its approach to Toronto, “the ruffians who had committed the outrage jumped from the car and escaped,” the newspaper said. Presumably they went on to enjoy their spoils, for there is no record of them ever having been caught.

The Richmond Hill-York Herald wrote in an article on November 19 that “it may be thought strange that no one on the train, excepting the two men fettered and bound should have known anything whatever of this gigantic depredation.” The article explained that the robbed compartments were isolated from the other parts of the train. “Moreover,” the story read, “the noise made by the engine would prevent any cries from being heard and thus the train arrived at the Queen’s Wharf with several hundred [passengers] in the rear… little knowing that a robbery almost romantic in its incidents, had been perpetrated within a few feet of them.”

Canada’s first train robbery followed a wave of post-American Civil War railway heists south of the border that began in 1866 as a consequence of unemployment and general lawlessness in the United States.

The Ku Klux Klan-style disguises donned by the robbers were similar to those worn by the notorious Confederate guerrilla fighter Jesse James and his associates when they derailed and robbed a train in Iowa a year earlier, killing two rail employees. However, there was no evidence that the James-Younger gang was linked to the Canadian heist.

The next Canadian train robbery would not happen until thirty years later, when American outlaw Bill Miner and his accomplices robbed a CPR train in Mission, B.C. Miner, who was sixty years old and known as the “gentleman bandit,” quipped, “Goodnight boys, sorry to have troubled you,” during the 1904 robbery. Miner was caught after a similar train heist in the same area in 1906, but he escaped from prison and fled to the United States, where he resumed his life of crime.