Len,

In general I think you are correct, but I think you may be oversimplifying the situation of the James boys and Youngers. Their experience in being hunted for four years duing the Civil War with the threat of automatic extermination of them by Federal forces upon capture had to have had a traumatic experience on them and their psychological makeup. And there was nothing easy about being shot at and wounded continuously, like most of them were in the years of robberies. And I've never read anything to support the idea that they made a lot of money in their lives of crime. They just got by, and even took menial jobs at times to support themselves and their families. But you are correct in your sssumption that their lives as guerrrillas gave them a perspective toward law and order than was unusual and made them more susceptible to a life of crime. As early as 1863, a reporter named Chase for a Leavenworth newspaper said:

"A Bushwhacker is a rebel Jayhawker, or a rebel who bands with others for the purpose of preying upon the lives and property of Union citizens. They are all lawless and indiscriminate in their iniquities. Their occupation, unless crushed out speedily, will end in a system of highway robbery exceeding anything which has existed in any country. It excites the mind, destroys the moral sensibilities, creates a thirst of wild life and adventure which will, on the restoration of peace, find gratification in nothing but highway robbery."

It's interesting to note, of course, that some Jayhawkers also took up lives of crime, Like Marshall Cleveland--before the Civil War even ended. See the following excerpt from my book (those who desire footnotes may check out some of the forty some copies found in local libraries) :

"One of Jennison’s leaders who fought in the last two Missouri actions was Charles Metz, alias Marshall Cleveland, an ex-Missouri penitentiary convict, later a commander of a company of Jennison’s Seventh Kansas Volunteer Cavalry (soon to be dubbed “Jennison’s Jayhawkers” or the “Southern Kansas Jay-Hawkers,” as they preferred to call themselves). Cleveland distinguished himself in the Morristown operation by killing Reverend Martin White, the killer of Frederick Brown (John Brown’s son, who was killed during Atchison’s 1856 invasion of Kansas). Apparently, White’s killing was not motivated by revenge; Cleveland merely sought White’s mule and White refused it. Later in the summer, Cleveland and John Steward returned to Missouri to continue freelance plundering. As a result of these raids, by early July, James Montgomery reported contrabands (slaves) streaming into Kansas by “brigades.”

. . . . Company H, composed of many of Jennison’s original Jayhawkers, became the most notorious unit in a notorious brigade. Ex-convict Marshall Cleveland, the captain of H Company, the “black horse company,” has already been mentioned for his exploits in Missouri in early 1861. Many of Cleveland’s colleagues saw him as an authentic swashbuckler. But his discipline was poor, and his tenure short in the brigade. In fact, he failed to survive its first formation. When Daniel Read Anthony called for a “dismounted parade” of the regiment, acting in Colonel Charles Jennison’s behalf, Cleveland turned out for the formation “in a somewhat motley garb--a soft hat, a regulation coat, drab trousers thrust into low-topped riding boots, a belt carrying a surplus of revolvers and a saber that seemed a hindrance.” When Anthony censured Cleveland publicly for his incorrect uniform, Cleveland indulged in a loud shouting and cursing match with Anthony, then mounted his horse and rode off to pursue his own freelance, no-holds-barred Jayhawking operations.

Cleveland was tall, erect, and a dead shot. One of his colleagues in Jennison’s regiment, Simeon M. Fox, said that had Cleveland dressed the part, he would have been the “ideal of an Italian bandit.” Fox described Cleveland as being thin of visage, “his complexion olive-tinted and colorless,” with “black, piercing eyes, finely cut features, dark hair and beard, correctly trimmed, complet[ing] a tout ensemble.” Cleveland soon attracted a number of men to his gang from Jennison’s old organization, all of whom, according to Fox, were “degraded ruffians,” “dissolute and dirty desperadoes.” One thing particularly remarkable about their appearance, he said, was that some of them had dyed their mustaches a “villainous metallic black,” marking them as “irreclaimable scoundrels.” Cleveland soon made his headquarters in Atchison, Kansas, where he dubbed himself the “Marshal of Kansas.” He virtually controlled the town, using it as his base of operations for Jayhawking runs into northwest Missouri’s rich farming communities and for robbing wagon trains, banks. On November 16, 1861, Cleveland’s gang robbed the Northrup and Union Banks in Kansas City. Finally, he became such a pest to the army in Missouri and Kansas that Company E, Sixth Kansas Cavalry, surrounded him near the Marais des Cygnes River and shot him dead. His so-called “brevet wife” later placed a tombstone atop his grave in a St. Joseph cemetery with the epitaph: “One hero less on earth/ One angel more in heaven.”

If any of this information is incorrect, please let me know.

The Younger's situation was further exacerbated after the war because of warrants for Cole Younger's arrest for a war-time killing, which made it difficult or impossible for him to return to a peaceful life. So it's best to judge these men based on their unique circumstances rather than judging them ordinary criminals. Both the James and Younger families before the war had impeccable reputations, and both families were prominent in the Border War counties of Missouri.

Don Gilmore

P.S. I'm the author of two articles about the James gang, "Showdown at Northfield" and "When the James Gang Ruled the Rails," plus, I am the author of Civil War on the Missouri-Kansas Border and two articles on the Border War, "Revenge in Kansas, 1863" and "Total War on the Missouri Border," a prize-winning article in Journal of the West, at Kansas Statte University. So I know a little about the subject, but a lot can be learned from the sources mentioned earlier. Settle's book is particularly well researched.