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Manitoba History: Jesse James and the “Great Winnipeg Manitoba Raid” of 1876?

by Brian Hubner
Winnipeg, Manitoba

Number 52, June 2006

This article was published originally in Manitoba History by the Manitoba Historical Society on the above date. We make it available here as a free, public service.

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If you were anywhere near Winnipeg last October [2005] you cannot have failed to notice that part of a major Hollywood movie entitled The Assassination of Jesse James by the Coward Robert Ford was being filmed in the Exchange District. Jesse James, as played by Brad Pitt, made a brief appearance in the Winnipeg scenes, but it is possible that had the fates allowed, the real Jesse would have been in Manitoba for a much longer stay. There are at least two contemporary sources which mention that Manitoba may have been considered when the gang (including his brother Frank, and Cole, Jim and Bob Younger), was planning what became the “Northfield Minnesota Raid” of 7 September 1876. The raid was a fiasco for the outlaws ending with most of them dead or in prison. Only Frank and Jesse escaped to Dakota Territory, and then made their way back home to Missouri.

Hollywood star Brad Pitt portrays Jesse James in the 2006 movie The Assassination of Jesse James by the Coward Robert Ford, partly filmed in Winnipeg.
Source: Warner Bros. Entertainment Inc.

J. T. Younger, uncle of the Younger brothers, reported that Jesse and his gang may have wanted to retire and settle in Canada (Winnipeg is due north of Northfield) but were forced on route to change their plans when they lost their money gambling. [1] Frank Triplett, author of The Life, Times, and Treacherous Death of Jesse James, written at a rate of sixty pages a day for publication only weeks after the assassination, and later suppressed by Jesse’s widow Zee, mentions a slightly more probable story. The following passage from the book is worth quoting at length:

Cole Younger was for a bolder move. Tired of this continual riding and raiding, he had made up his mind to make one more grand stroke, secure a big booty, and retire to some foreign country, since he could have no peace in his. With this aim in view it is perfectly natural that he should desire to make this next stroke not only a successful one, but not a gathering of trivial spoil. It is said that he urged some rich town in Canada. In support of his proposition, and against that of Chadwell [the Northfield raid], he insisted on the fact that the Canadians were a people less inured to fire arms than of the Americans, certainly less so than the hardy borderers of Minnesota, and that, in consequence, a rush such as they contemplated would utterly terrorize them and place them completely at the bandit’s mercy. They are said to be a quiet orderly people, not used to the pistol and knife combats of the Americans; they are men who settle a difficulty with their fists, or in their courts, and half a dozen desperate and well-armed men could ride through the biggest city in Canada and come out alive. You will find on the other hand, that the people of Minnesota, like all borderers, are inured to sudden broils, and that the explosion of pistols in their streets will not terrify them; and besides, he added, by selecting Minnesota we place an immense number of railroads and telegraphs between us and retreat. [2]

The James boys and the Youngers would obviously have been better off to have made the journey to Winnipeg where there were few guns and the courts were the last resort of a real man, although I am not sure how “rich” Winnipeg banks were in 1876. At Northfield they faced an “explosion of pistols” not their own which ended the activities of the James-Younger gang for a long time and finally led to the violent death of Jesse in April 1882. In the end, Winnipeg had no choice but to settle for Brad Pitt for a day rather than reminisce about an elderly Jesse shopping for suspenders at Eaton’s.

Jesse Woodson James (5 September 1847 - 3 April 1882) was born in Centerville (now Kearney), Missouri and, with his brother Frank, fought with the Confederate irregular forces during the American Civil War. After 1865, he led former guerillas in the James-Younger Gang robbing banks, trains, and state fairs across the southern and southwestern United States. When the botched robbery at Northfield, Minnesota (7 September 1876) resulted in the death or capture of most of the gang, James recruited new members such as Charley and Bob Ford who assassinated him in St. Joseph, Missouri.
Source: Jesse James, 1875. St. Joseph Museum.


1. William Settle, Jr. Jesse James was his name. Columbia: University of Missouri Press, 1966, p. 95. The ultimate source for this is indicated as the St. Louis Republican, 22 October 1876. This tale was recently repeated in the Winnipeg Free Press while filming was in progress for The Assassination of Jesse James. See Morley Walker, “Was famous outlaw hoping to become a Winnipegger?” Winnipeg Free Press, 22 October 2005.

2. James Triplett. The Life, Times, and Treacherous Death of Jesse James. First published in 1882, reprinted in 1970 by Sage Books of Chicago, p. 136.

Page revised: 2 June 2012

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