The Kansas-Missouri border, the subject of a number of free state vs. slave state compromises that postponed the US Civil War, was a trouble spot even before the war: Kansas was nominally a free state, while Missouri allowed slavery. When Union troops invaded Missouri in 1861, they had to contend with both Confederate troops and a number of guerilla bands, including one formed by William Quantrill. Two of the members of his band were Jesse James's older brother, Frank, and Cole Younger, the son of a slaveholding family. In addition to ambushing Union troops, Quantrill's Raiders terrorized civilians, such as the 1863 massacre of 200 unarmed men and boys in Lawrence, Kansas.
In his 1865 second inaugural address, Abraham Lincoln visualized an American future "with malice toward none, with charity for all." It didn't turn out that way. As losers (1865), the South endured a number of humiliations and indignities from the North, and some of the rebels wouldn't quit: after Quantrill was killed, his Raiders continued to harass border states under two other leaders (both also killed) until Frank and Jesse, along with the Younger Brothers (Cole, Jim and Bob), modified their tactics to form the James-Younger gang in 1866. It was successful because it concentrated on two rich entities that common folk perceived as Northern enemies: railroads and banks. They gained a Robin Hood reputation by robbing numerous banks; they didn't rob a train until 1873.
In September, 1876, 8 members of the gang took a train to St. Paul, Minnesota, rented horses, and set out to rob the Northfield bank. They chose it because two retired Union generals, Butler and Ames, owned stock in the bank. The robbery was a fiasco: they killed the cashier, but got no money. Citizens opened fire and killed two of the robbers outside the bank. A large posse trailed the rest, catching the Youngers at Madelia, Minnesota. The James brothers escaped and headed back to Missouri.
The Youngers pled guilty in order to avoid hanging, and were sentenced to life at the state penitentiary at Stillwater. Bob died of TB in 1889 (Jesse had been killed in 1882), while Cole and Jim were paroled in 1901. Jim killed himself a year later, but Cole partnered with Frank James in 1903 to tour as the Cole Younger & Frank James Wild West Company, demonstrating their raids and giving lectures on how crime doesn't pay. Frank died in 1915, and Cole, aged 72, died a year later.
This song is obviously not Cole's composition (although he was a model prisoner), and was probably a poem written for a northern newspaper before 1882, as it says Jesse was still alive. John Lomax collected a version for his 1910 Cowboy Songs. This somewhat different rendition was recorded by Texas cowboy singer Edward L. Crain in 1931, and re-released on the Folkways Anthology of American Folk Music. Dock Boggs recorded a fragmentary version using the Roving Gambler tune (Dock Boggs, The Folkways Years; Smithsonian-Folkways SFW40108), so when in 1965 he performed at St. Olaf College in Northfield, he was visibly excited when he learned you could still see the bullet holes in the wall of the old bank building. We went there after the concert and took a picture of him in front of it as a tribute to tradition and those interested enough to keep it alive.
I am a noted highwayman, Cole Younger is my name;
'Tis deeds and desperation that brought my name to shame.
Robbing of the Northfield bank is a thing I'll never deny,
But which I will be sorry of until the day I die.
We started for old Texas, that grand old Lone Star State;
'Twas there on Nebraska prairies the James Boys we did meet.
With knives, gun, and revolvers, we all sit down to play
A game of good old poker to pass the time away.
Across Nebraska prairies a Denver train we spy.
I says to Bob, "We'll rob her as she goes rolling by."
We saddled up our horses, northwestward we did go
To the godforsaken country called Minnie-soh-tee-oh.
I had my eye on the Northfield bank when brother Bob did say,
"Cole, if you under-to-take the job, you'll always curse the day."
We stationed out our pickets, up to the bank did go,
'Twas there upon the counter, boys, we struck our fatal blow.
Saying, "Hand us out your money, sir, and make no long delay.
We are the noted Younger boys, and spend no time in play."
The cashier, being as true as steel, refused our noted band.
'Twas Jesse James that pulled the trigger that killed this noble man.
We run for life, for death was near, four hundred on our trail.
We soon was overtaken and landed safe in jail.
'Twas there in the Stillwater jail we lay, a-wearing our lives
Two James boys left to tell the tale of the sad and fateful day.