Summary: In the first chapter of this series we looked back at the beginnings of Frank and Jesse James’ rise to underworld power in theearly years of Prohibition. In this segment we’ll review the Jamessyndicate’s expansion into the Chicago area and the resulting fierce gang war between the James brothers and Al Capone’s mob.

By 1924 there was hardly a bottle of liquor in the Kansas City area that didn’t have some connection to the James syndicate; besides their network of speakeasies and underground distilleries, the James brothers had set up a number of illegal breweries from which to make beer for the benefit of those of their clients who wanted it. And if they couldn’t make enough of it in their own facilities, they either bought more from co-operative brewers in St. Louis or hijacked it from rival syndicates who’d gotten careless in guarding their supplies. The long arm of the law didn’t seem to be quite long enough to put a crimp in Frank and Jesse’s illicit alcohol business, and most of the would- be challengers to their domination of the Kansas City underworld were long since dead or(with the aid of corrupt policemen on the brothers’ payroll) sent to jail.

But as the James syndicate continued to reinforce and expand its power base, it was confronted by a highly formidable obstacle to Frank and Jesse’s plans to extend their reach into Chicago-- specifically, a certain Alphonse Capone. Al Capone had been ruthless about destroying potential rivals on his own turf; he certainly wasn’t going to take it lying down when outsiders tried to muscle in on his territory. A long, bitter war between the Capone and James syndicates was inevitable and both sides would rack up a massive body count before it was over. The first shots of that war were fired in March of 1928, when three gunmen from Capone’s old neighborhood in Brooklyn attacked and killed a truck driver in the employ of the James syndicate as he was traveling on the highway between Kansas City and St. Louis.

The James brothers didn’t waste much time retaliating-- only two days after the driver’s murder, Cole Younger and two of his brothers firebombed a Capone distillery in Joliet, Illinois and wounded Frank Nitti, Capone’s right-hand man, in an assassination attempt. In a rage Capone put a $50,000 bounty on Cole Younger’s head and vowed to burn Frank and Jesse James’ home in Kansas City to the ground with both men in it. Although he never got the opportunity to make good on his arson threats against the James house, the fact that he issued those threats was a clear signal as to just how far he was willing to go to destroy the James gang.

The war between the James and Capone syndicates would last nearly a year and a half, with both sides taking massive casualties as the James brothers fought not only to expand to Chicago but also to keep their own turf in Kansas City and St. Louis from being lost to their scar-faced nemesis. As part of their campaign to smash the Capone mob Frank and Jesse James struck a deal with another of Capone’s enemies, Bugs Moran; in return for Moran’s assistance in destroying the Capone organization, the James brothers would make Moran a major partner in their syndicate’s Midwest operations. Moran’s associates Dion O’Banion and Hymie Weiss, who had their own scores to settle with Capone, were only too happy to acquiesce to Moran’s wishes in forming the alliance.

The James-Moran coalition landed many devastating blows on the Capone syndicate, and for a long time it looked as if the war might end in a decisive victory for the James brothers and Moran. But on February 14th, 1929 their fortunes took an abrupt and serious turn for the worse in an event now immortalized in American crime folklore as “the St. Valentine’s Day Massacre”. Seven men known to be affiliated with the James and Moran organizations were lured to a downtown garage in Chicago by a note from a man claiming to have information about a police mole within the James syndicate and requesting a secret meeting with members of the James and Moran crews; among the seven who turned up in response to the message were two of Cole Younger’s brothers, Jim and Bob. When the seven gangsters turned up at the garage, however, a nasty surprise awaited them-- or rather ten nasty surprises. Al Capone had dispatched ten of his best enforcers to the garage with orders to lie in wait until the James-Moran associates arrived, them ambush them before they realized what was happening. All ten of them were sporting Thompson submachine guns and were experts at using them.

It only lasted two and a half minutes, but in that short time six of the seven James-Moran associates were killed instantly, and the one man who wasn’t was so severely wounded he could barely manage to crawl to the garage door before a Capone gunman finished him off with a pistol shot to the head. Federal agents searching the garage the next day found hundreds of bullet casings littering the floor as well as bloodstains on nearly every wall and even a few small traces of brain matter lodged in a drainpipe. An infuriated Jesse James was moved to swear vengeance on the Capone syndicate and offered a $10,000 reward to anyone who could provide information leading to the location and death of the principal conspirator in the garage hit. He’d never live to pay that bounty, as it turned out...

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....and shortly after the St. Valentine’s Day Massacre the James and Moran syndicates would find themselves put squarely on defense not only by Capone’s mob but also by the long arm of the law. Knowing how endemic corruption was within Chicago’s police department, the federal government had tasked the Treasury Department to send one of its best field agents to the Windy City to take on and crush the illegal liquor trade there. Although not quite the one-man army which later films and television series would make him out to be, Eliot Ness did do quite a bit to break the power of the Chicago mobs-- and he wasn’t shy about confronting their enablers either. Assembling a team of agents dubbed “the Untouchables”, Ness quickly set to work attacking both the mobs themselves and the corrupt politicians whose coziness with men such as Al Capone and Jesse James helped make those mobs’ operations possible. The first significant gangland casualty of Ness’ crusade to wipe out Chicago’s illegal liquor barons was Bugs Moran, whose luck finally ran out on the night of October 28th, 1929 when he and his two most trusted enforcers were killed in a brief but ferocious shootout with federal agents as they were trying to escape arrest for their illegal actions in Moran’s quest to destroy the Capone organization.

Under any other circumstances Moran’s violent demise would have been the biggest story on the front page of America’s newspapers the next morning. But just hours after Moran met his end, the stunning announcement came from New York that the Wall Street stock market had crashed. The worst economic catastrophe of the 20th century, the Great Depression, had descended on the world and the already weakened power base of the Chicago syndicates was about to diminish still further as profits from the bootleg liquor trade started to dry up....

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...to say nothing of what was happening to the James brothers’ underground empire in Kansas City and St. Louis. For many of the loyal patrons at their nightclubs and speakeasies the first sign of a depression was not the massive headlines about the market collapse in New York but a modest three-column article on page five of the October 31st, 1929 St. Louis Post-Dispatch announcing the temporary closing of the Rio Grande nightclub, a popular James syndicate-owned nightspot that in its heyday had been dubbed “the Cotton Club of the Midwest” by an admiring visitor from New York. The Rio Grande had been one of the most profitable branches of the James syndicate tree, but when the stock market self-destructed the club lost one of its most important sources of revenue-- at least half of the club’s most loyal patrons had been stockbrokers who’d made handsome profits on both the Wall Street markets along with the mercantile boards in Kansas City and Chicago, and those profits were gone now that the New York stock market had tanked.

The James brothers tried to recoup their losses through numbers rackets and forged stock certificate schemes, but nothing seemed to work. By the summer of 1930 nearly half of their original nightclubs and speakeasies had gone out of business and the rest were hanging on by the slenderest of threads. Having been able to achieve only a grim stalemate in their conflict with the Capone syndicate, Frank and Jesse now found themselves decisively losing the battle to prevent their own organization from collapsing in ruins. The borders of their underworld kingdom steadily shrank as federal law enforcement agents initiated a series of raids against James front companies and enforcers from rival crime syndicates lashed out against the James syndicate in retaliation for the violence the James had itself inflicted on its foes during the eleven years since Prohibition had been enacted.

But perhaps the greatest wound the James organization would endure after the Great Depression started came on January 27th, 1931 when the mole who had been feeding the James brothers information regarding the Kansas City police department’s operations against their syndicate was finally exposed and arrested. With the mole locked up, Frank and Jesse lost a critical intelligence source-- a loss that would turn out to be the biggest nail in the James organization’s coffin when it eventually met its demise....

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