A lively tale of a charming bandit and proto-terrorist prompts Mark Simpson to wonder why we’re still thrilled by ruffians.

(Independent on Sunday, 5/1/2003)

Why, after so many years, are we still so hot for outlaws? As popular culture and news bulletins keep reminding us, Rebels, Robin Hoods, bandits, gangsters, serial killers and terrorists continue to exert a sweaty grip on our imaginations. 

Is it because, to strike a Nietzschean pose (riding crop in hand), those who are not sadists are necessarily masochists? Are we all secretly itching to be held up, tied up and blown up? Is civilisation such a non-experience that we need a – preferably young, attractive and well-dressed – feral-eyed brute to slap us out of our dullard drowsiness?

Or is it because, having surrendered our own sadism to civilisation, we need someone who will rob and kill on our behalf? Someone who will, in other words, be “free” for us: an emotional lottery winner justifying our own pitiful, ticket-stamping repression – hence the need to make them very, very famous? Are “sociopath” and “psychopath” just names we like to call those who have more guts for life than us, but not enough education to know what we mean?

Jesse James, “last rebel of the American Civil War” and one of the first rebels of the modern age, didn’t have much of an education, but he certainly had an answer. “We are the boys that are hard to handle,” he declared in one of his many swaggering missives to the press, “and will make it hot for the party that ever tries to take us.”

Or, as Robert Pinkerton, the head of the famous Chicago-based detective agency humiliated by James after trying to “take” him, put it: 

“His gang killed two of our detectives and I consider JJ the worst man, without any exception, in America. He is utterly devoid of fear and has no more compunction about cold-blooded murder than he has about eating his breakfast.” 

High praise indeed from Mr. Pinkerton, whose men firebombed James’ mother in her home, maiming her and killing his young half-brother, and were to become the hired goons of strike-breaking US businessmen.

The passengers on the St Louis-Little Rock express flagged down and boarded at Gads Hill, Missouri, in January 1874 knew better than to try to take on Jesse, an irresistible mixture of sociopath and southern gent. “We do not want to rob workingmen or ladies,” declared the tall, handsome, finely dressed and feral-eyed outlaw to the stunned passengers on the express, “but the money and valuables of the plug-hat gentlemen are what we seek.” 

Stunned not just at being held up at gunpoint, but that the gun in their face should belong to the famous Jesse James. As the celebrity outlaw walked down the passenger car, playfully exchanging hats with members of his captive audience, his elder brother Frank recited his favourite author, William Shakespeare, while their bandit buddies busied themselves unburdening the male passengers of their cash and valuables. When one man introduced himself as a minister, they promptly returned his money and asked him to pray for them, like the good Baptist boys they were. Likewise, after pocketing the conductor’s gold watch they returned it sheepishly when the baggage master protested: “For God’s sake, you won’t take it for it is a present.”

After courteously shaking the hand of the engineer and cheekily advising him always to stop at a red flag, the bandits departed on their horses in a cloud of dust and rebel yells. The crew then discovered the final and possibly most important act of the Jesse James Show: a prepared press release left behind with instructions that it be telegraphed to the St Louis Dispatch, a sympathetic Confederate-Democratic newspaper. “The most daring robbery on record!” it began modestly. 

“The south bound train on the Iron Mountain railroad was robbed here this morning by five heavily armed men and robbed of dollars — There is a hell of excitement in this part of the country.” 

The figure to be filled in the blank space would amount to $2,000 – not a vast sum of money, even back then, especially when divided five ways. However, as was often the case with Jesse’s performances, the hold-up was a priceless public relations coup.

Jesse and Frank were sons of a pro-slavery Baptist preacher who died in 1850 in the California Gold Rush when Jesse was just three, and a fiercely patriotic and dominating Southern mother, Zerelda, whom everyone seems to describe as “formidable”. Both brothers fought in the Civil War (1861- 1865), Jesse joining up at the stripling age of 16, serving with some of the most brutal and successful Confederate guerrillas, or “bushwhackers”. They conducted a war of annihilation against Unionists in Missouri, casually but systematically murdering their Federalist neighbours and freed or runaway blacks.

Missouri was a border state, and hence nowhere was the American Civil War more “civil” – that is to say, terrible. In the war of secession, civilisation lost to its malcontents and Jesse emerged a leader of these: despite the chivalry – and showbiz – of hold-ups like the one at Gads Hill, Pinkerton’s cold assessment of James was on the money.

As TJ Stiles’s Jesse James: Last Rebel of the Civil War , billed as “the first major study of Jesse James in 40 years”, shows, James was both the product of this cataclysmic struggle and its legacy: after the South surrendered at Appomattox, ex-guerrilla banditry became a symbol of Confederate resistance to Reconstruction and the Radical money-men’s plans for emancipation in the South, as well as a political instrument of the Confederate wing of the Democratic Party. Without popular and political support, James’s criminal career would have been cut short much sooner; in fact he was only brought to account  – a fellow bandit assassinated him to collect on the $20,000 reward posted by the railroads – long after his popular support and political usefulness had receded.

Stiles argues James was neither a Robin Hood (he didn’t always rob from the rich and certainly did not give to the poor), nor a Wild West figure (he was politically motivated), but instead a proto-terrorist: 

“a transitional figure standing between the past and the industrial, violent, media-savvy future, representing the worst aspects of both”. 

While this may be a convincing argument, it perhaps mistakes what a Robin Hood or an outlaw – or, for that matter, a terrorist – is. Mr. Hood was popular not because he actually stole from the rich and gave to the poor: rather, his popularity was expressed and excused in the myth of his stealing from the rich and giving to the poor; that is, the fantasy of him stealing and killing on our behalf

Sure, Jesse James became a political symbol of resistance to Reconstruction, but more profoundly he also became a symbol, as all outlaws do, of resistance to civilisation and its repressions. The political resonance legitimised the enjoyment of his psychopathic freedom, at least to Confederates. Perhaps this is why his reputation of Southern courtliness was so important: courtesy and wisecracking from a man with a gun in his hand is perhaps the greatest expression of freedom, terror and, to ‘noble’ superiority.

Ironically, Jesse himself was anything but free. It was his ability to recognize and play the role assigned to him by society, history and family which guaranteed his lasting fame. Like other famous Good Bad Boy rebels that were to follow in his footsteps, from Elvis to Eminem, it was his momma he had to thank for that showbiz talent. The strength of Jesse’s narcissistic mother-son bond can be estimated by the fact that the woman he married was his first cousin and named “Zerelda” after his mother. As the Kansas City Times wrote of the original “Zee”: 

“She is a woman of great dramatic power. The James family are nothing unless dramatic or tragic.”