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The “Chicago Way” Goes Nationwide

Daniel J. Kelley 21 May 2010 12 Comments

“Obama learned his lesson well.” — quote attributed to L. David Alinsky, son of Saul Alinsky.

From time to time, media reports have referred to a unique brand of systemic corruption and political hardball tactics as being “the Chicago Way. “ The term is taken from the motion picture adaptation of “The Untouchables.” The screenplay was written by David Mamet. Although the exploits of Eliot Ness were exaggerated in the film, much like the original television series which often dispensed fiction for fact, the drama nonetheless struck a responsive chord.

On a political level, this brand of thuggish behavior has even influenced members of the President’s inner circle. Obama’s power mad Chief of Staff, Rahm Emanuel, has established a reputation for speaking in a non-stop string of obscenities, repeatedly stabbing a steak knife into a table top to emphasize his points, and allegedly sending a dead fish to a political opponent. One can almost imagine the nebbish David Axelrod as the successor to Jake “Greasy Thumb” Guzik, while the late and, in some quarters, unlamented Congressman Jack Murtha of Pennsylvania seemed quite capable of going full Nikita and pounding his shoe on the table like Kruschev as he damned the American military and accused his own constituents of being racists for preferring McCain over Obama in 2008. Secretary of State Hillary Rodham Clinton famously wrote her undergraduate thesis paper on Alinsky’s community organizing techniques.

The vicious and deceitful tactics employed by this administration are in no small part attributable to the sinister influence of the late Saul Alinsky upon the occupants of the West Wing. It is appropriate that Alinsky be given his proper due as the political Godfather of Obama’s gangster government at long last since one of the less widely reported aspects of Alinsky’s pedigree was his apprenticeship with the Chicago Syndicate.

As a University of Chicago graduate student, an institution that would later figure prominently in Obama’s own career, Alinsky sought out the company of members of the Capone organization by hanging around at the Lexington Hotel on South Michigan Avenue. Initially, the low level gangsters ignored Alinsky’s presence, but he finally gained their confidence by befriending “Big Ed“ Stash. Alinsky, the son of Russian Jewish parents, was studying criminology and sociology and the Lexington served as Capone’s principal Chicago headquarters in the early Thirties.

After this initial introduction to the boys, Alinsky came to the attention of Frank “The Enforcer” Nitti. A one time barber who developed a profitable sideline business fencing stolen goods, Nitti eventually rose in the chain of command to become the leader of Capone organization’s punishment squad. When rival criminals were marked for elimination, Nitti hired the out of town killers and paid for the contract murders. Nitti later became the second in command in the organization and ran the Chicago mob during Capone’s frequent absences from the city. Following Capone’s conviction and imprisonment for income tax evasion in 1931, Nitti succeeded “Scarface” as the leader of the criminal gang.

Nitti was impressed that Alinsky felt that the mob was a subject worthy of academic studying. In time, he went a step further and hired Alinsky to serve as a bookkeeper and glorified office boy and placed him on a regular salary. From his inside position, Alinsky was able to learn lessons in extortion techniques that he would later employ in organizing in Chicago’s Woodlawn and the Back of the Yards neighborhoods.

Once Alinsky questioned the expenditure of $7,500.00 to hire a pair of professional killers from out of town to perform a high level assassination. He complained to Nitti that it was an extravagant waste of money when the Chicago mob had so many of its own gunsels on salary. Why import high priced, anonymous hit men for contract killings when so much local talent was ready on hand at comparatively cut rate prices?

Nitti took Alinsky aside and explained the facts of life to the student. Many of the Chicago mobsters were personally acquainted with one and other. Some had worked together for years. Others socialized with fellow hoodlums during their free hours, dining with each other’s families, attending ball games and prize fights together. It is a much more difficult task to shoot someone that you have had a long term association with. Out of town killers simply executed their intended targets and left the city. They were not expected to send flowers and attend the funeral services while pretending to mourn. Alinsky would later comment that Nitti had explained the meaning of a “primary relationship” to him better than any of his sociology professors.

Alinsky never occupied an important position with the Outfit and some of his disciples have tried to downplay or expunge this portion of his life from the historical record. The radical organizer was seen as Nitti’s personal protégé and no one objected to his quietly fading from the scene when his patron and sponsor lost his position and his life in 1943.

Nitti’s downfall coincided with a federal investigation of the mob’s extortion activities directed against the motion picture industry. For years, the mob demanded and received lucrative payoffs from Hollywood studios and theaters in return for providing “protection” from labor strikes that could cripple film productions and vandalism directed towards theaters. When the federal prosecutors moved in, Nitti was blamed by his associates for authorizing the Hollywood shakedowns and promptly deposed.

As the investigation neared its climax, Nitti committed suicide opposite the railroad tracks in suburban North Riverside. He was supposedly despondent about his loss of power, poor health and the prospect of another long period of incarceration. Nitti had previously been imprisoned for income tax problems of his own and he did not relish returning to the penitentiary. The county coroner opened and closed the investigative hearing in less than a day.

In subsequent years, several different leaders headed the Chicago Outfit, but Alinsky was effectively through after Nitti’s demise. In the Fifties, Alinsky testified before the Kefauver Committee on Crime, but apparently none of his remarks disturbed the mob bosses. He had simply taken the Senate committee members on a nostalgic trip down memory lane describing the activities of gang members who were long since dead or imprisoned. None of his testimony was particularly relevant or sensational.

While many of the lessons that Barack H. Obama learned as “a community organizer” have been attributed to his training and reading Alinsky’s “Rules for Radicals,” it is worth noting how similar some of the methods are those to those routinely employed by organized crime. Misleading the public with blatant propaganda, calculated deceptions and outright lies are familiar Mafia tools. Likewise, gaming the political process, promoting vote fraud at the polls and bribing venal politicians to secure their votes are time honored methods utilized by the gangsters. The Chicago Syndicate once dominated the political life of the West Side and the most corrupt politicians in the General Assembly were frequently referred to simply as “the West Side Bloc.” The primary role of this particular group was to act as obstructionists who would bottle up important reform legislation and prevent its passage through a combination of chicanery and occasional smear tactics.

When Alinsky returned to his community and labor organizing efforts, he put to good use some of the techniques that he had learned from Nitti. In the years following the repeal of Prohibition, the Mob had to find alternative methods of raising revenue. While vice profits from gambling and prostitution activities continued, labor union racketeering grew in importance. Controlling and monopolizing bar and restaurant supply services was also highly profitable and Nitti once claimed to look forward to the day when the Syndicate realized a profit from the use of a single olive in every martini. The Mob achieved these ambitions by co-opting numerous labor unions.

While Alinsky proposed that his followers engage in a march through the institutions as a quiet method of gaining political power, the mob similarly sought to infiltrate labor unions and to establish profitable rackets. Al Capone, himself, once stated that if rank and file union members saw a few additional dollars in their pay envelopes, the majority of the members would hardly concern themselves with mobsters seizing control of their union locals and using the political power of the organizations for their own nefarious purposes. In a like fashion, Obama has promised the country virtually free health care and a pristine environment. The payoff methods that his administration has used to obtain votes from legislators have bordered upon open bribery. Obama’s primary interest is not in achieving these largely unattainable goals, however, as much as it is about enlarging the size and scope of the Federal government and thereby increasing his own power.

One thing that the political thugs and make believe tough guys in the Obama White House have overlooked is that most of the Chicago Syndicate members privately held the opinion that their bought and paid for political allies were little better than paid prostitutes. The job of passing bribes to politicians was often entrusted to lower level hoodlums.

This is “the Chicago Way” writ large, indeed.


Daniel J. Kelley is a regular contributor to “The Chicago Daily Observer.”


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    For more detail about the mechanics of the Obama Machine’s lawlessness and enabling prostitutes within the bureaucracy, media, and law enforcement, see http://www.butterdezillion.wordpress.com and click on the link at the bottom of the post.

  • Jim Ridings said:

    What a great article! Mr. Kelley not only tells of little known, or to a large extent unknown, information about the Mob and the Chicago Way, he also tells of its connection and its similarity to the radical element in America. And he reveals how it is connected to the radicals in Obama’s Chicago Way Administration. This article should be read by anyone who wants to understand Obama’s ways and his means. The radical Leftist regimes in Europe and Russia in the 1930s are not dissimilar; history is not in the past, it keeps going on and repeating itself.

  • RB said:

    Frank Nitti took over the BSEIU (Building Service Employees International Union)in 1933. The BSEIU eventually became the SEIU.

  • Pat Hickey said:

    Sound and sure footed historical perspective, Mr. Kelley, as always.

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  • Roseann Graham said:

    What a wonderful piece of true journalism. The American public has a right to know who has a choke-hold on their country. God save America!

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