They were two of the most notorious bootleggers of the Prohibition era; at the height of their careers they were masters of an underworld empire whose scope and power was surpassed only by that of Al Capone’s Chicago syndicate. They were Frank and Jesse James, and they ruled the Kansas City mob as their personal dominion for much of the 1920s and a good part of the ‘30s before the long arm of the law finally caught up with them. Their eventual demise is one of the most famous chapters in the annals of American crime; in particular, the story of Jesse James’ 1935 assassination by a rival gangster has become an integral part of the folklore of the Prohibition years. Countless books, films, theater works, and even a Broadway musical have been inspired by the brothers’ outlaw activities. In another time they might have been train robbers or meth lab operators-- one of their associates did, in fact, actually have a brief stint running a heroin ring in the South after the James brothers’ original syndicate collapsed.

Besides being ruthless gangsters in their own right, Frank and Jesse James enlisted a rogues’ gallery of cutthroats and bomb-tossers to enforce their will in the Kansas City underworld. Modern estimates by the FBI’s Kansas City office attribute at least 15 percent of the murders committed between 1921 and 1927 either directly or indirectly to the James brothers mob; the brothers themselves are known to have personally killed thirty-one people. Their chief enforcer, former U.S. Army machine gunner-turned-professional assassin Cole Younger, killed at least twenty people on the James mob’s behalf and five more at his own initiative.

Jesse James was born September 5th, 1900 near Kearney, Missouri. Though younger by four years than his brother Frank(born 1896), Jesse was to a significant extent the more dominant of the sibling duo. The 1903 death of their father Robert, a farmer and Baptist minister, had a traumatic effect on the family and might have been the tipping point which ultimately pushed Frank and Jesse into a life of crime; Jesse’s first arrest came in the summer of 1910, when he was caught attempting to break into a local general store to get the proceeds from its cash register. He said his mother needed the funds to keep a roof over the family’s head.

A hint of the more violent path his life was to take came in April of 1912 when he was sent to jail for assault and battery during the same week that Boston’s Fenway Park opened for business and RMS Titanic sank on her maiden voyage across the Atlantic. The specific circumstances leading up to the assault are still somewhat mysterious, but generally it’s believed a long-standing personal dispute between Jesse and a neighbor’s son may have been a major factor. Police and hospital records of the assault indicate that although the other boy outweighed Jesse by more than fifty pounds he inflicted such serious injuries on his antagonist that the other boy had to be hospitalized for two weeks.

By the age of fourteen Jesse had organized his own street gang and was a familiar face to many on the Kearney police force; at sixteen he was booked for auto theft.  Barely a week after his 17th birthday, he went to jail on a charge of illegal gun possession, spending six full months behind bars before being released on a technicality when it was discovered that two of the key prosecution witnesses at his trial for that charge had perjured themselves on the stand. But it may have been the ratification of the 18th Amendment to the Constitution in 1919 and the passage of the accompanying Volstead Act, both of which banned the sale or use of alcoholic drinks, which proved to be the tipping point in permanently ensconcing Jesse in a life of crime. He recruited Frank to join him in setting up an underground distillery to meet what they both correctly anticipated would be a heavy future demand for illegal liquor...

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....and within eight months after Prohibition went into effect the James brothers opened their first speakeasy in Kansas City. They didn’t have to wait too long for customers to start flocking to their doorstep; within two days there was a line stretching two full blocks in front of the speakeasy’s door and its cash registers were filled to bursting. Their first purchase with their newly accrued profits from the speakeasy was a headstone for their mother Zerelda, who had died of heart failure shortly after Prohibition went into effect and been buried under a wooden cross because the family couldn’t afford granite markers at the time.

Their second purchase was the services of Cole Younger as their chief insurance policy against having their burgeoning bootleg liquor empire disrupted by rival gangsters or by law enforcement. To say that Younger was skilled in the use of firearms would be an understatement: besides being proficient in the use of machine guns Younger, a veteran of World War I who had personally killed twenty Germans in one day as an infantry corporal on the Western Front, was also pretty handy with a shotgun or a pistol. His brothers were no slouches with guns either, as the James-Younger syndicate’s rivals and more than a few state and federal law enforcement agents would discover over the next decade.

Less than a year after the James brothers opened their first speakeasy, they controlled the largest bootleg liquor operation in Kansas City and had also established a considerable foothold in the St. Louis area. Using a tactic that would later be employed to great effect by Al Capone in his conquest of the Chicago underworld, Frank and Jesse channeled a substantial amount of the proceeds from their bootleg liquor operations toward soup kitchens serving Kansas City’s less fortunate citizens. By doing so, they encouraged some segments of the press of those times to view them as romantic outlaws rather than cold-blooded killers; they also earned a substantial degree of personal and collective loyalty from the lower classes in the Kansas City social order, who would later constitute some of their staunchest defenders when the law began cracking down on Prohibition violators. To further cement their dominant place in the Kansas City underworld, the James brothers revived an old outlaw tactic from the days of the Wild West known as “bushwhacking” and gave it a 20th century spin-- in this new version of the technique, instead of men on horseback riding up to shoot homesteaders and torch farmhouses, James syndicate gunmen driving Ford Model A’s would strike rival gangs’ hideouts in a hail of tommy gun fire and Molotov cocktails.

To minimize the risk of such attacks being directly connected to the James brothers the gunmen would usually attack at night in order to cut down the chances of potential witnesses identifying them to the police. They would also disguise their faces by whatever means suited the time of year-- thick scarves and overcoats with high collars when the weather was cold, tinted sunglasses when the weather warmed up. If by some mischance a link between the James brothers and these attacks was suspected by the authorities, Frank and Jesse would invariably say they were the work of a few rogue hotheads who had gone off the rails. And there were plenty of corrupt policemen and attorneys who were more than willing to accept the brothers’ cover story for the right price-- the James syndicate paid thousands of dollars’ worth of bribes every week to ensure their operations in Kansas City and St. Louis were able to continue with as little disruption as possible.

But while their syndicate’s power was greatest in the Kansas City and St. Louis areas, they didn’t entirely lack influence elsewhere in America. Frank and Jesse had contacts in every major eastern city from New York to Atlanta to help them run and expand their criminal empire; in the Southwest James syndicate operatives worked around the clock to find and recruit skilled gunmen to replace those killed in fights with rival gangs. The brothers even owned a partial stake in a Los Angeles- based racketeering operation. And along the Texas-Mexico border there were gunrunners more than willing to supply the brothers with whatever firearms they needed to maintain their grip on power.

The Kansas City police were beside themselves with frustration trying to prove the James brothers had a direct link to the violence gripping the city. Few if any people were willing to talk to the cops about the true nature of the syndicate’s operations, and those people who did talk often had a nasty habit of winding up dead. Compounding the police department’s troubles was the corruption infecting much of the force and the resulting security leaks it created. At times there was a distinct and nagging feeling among Kansas City’s senior police officials that the James syndicate seemed to know of the department’s next move against the brothers before the department itself did...