Chicago’s Favourite son by Charles Glass

What did Barack Obama learn in Chicago that propelled him to the White House? The Democratic Party there was a tough school, renowned for dirty politics. Can the education he had from The Machine help him bring Washington to heel?


Illustration by Chris Riddell


 Until Barack Hussein Obama’s inauguration more than a year ago, no Chicagoan had ever seized the White House.That no one from the Windy City had achieved the presidency before 2009 seems perverse, given Chicago’s significance in national electoral politics. One measure of this importance is that the Republicans and Democrats have held more presidential nominating conventions in Chicago than in any other city – 25, compared to 10 for its nearest rival, Baltimore. Chicago’s clout and money were always welcome in national elections, even if its politicians were not sufficiently potable to sit uptable from the White House salt. Jack Kennedy said that he would not have won in 1960 without Chicago Mayor Richard Joseph Daley, a fellow Irish Catholic and old friend of Kennedy’s father. (When Illinois Republicans demanded a recount in 1960 of the famously unreliable Cook County vote, Daley agreed to check all the ballots at the rate of one precinct a day. “At that pace,” Mike Royko wrote in his magisterial biography, Boss: Richard J Daley of Chicago, “they would complete the recheck in twenty years.” A special prosecutor, who turned out to be a “faithful organisation Democrat”, eventually dropped all charges against the suspect polling officers.) Bill Clinton was so indebted to the second Mayor Daley, Richard Michael, that he made his younger brother William secretary of commerce.  

Chicago’s politicians were kingmakers, not kings.  Their legendary delivery of delegates at the Democratic Convention and electoral college votes to the Democrats’ nominee required contenders to feign ignorance of the ways the votes were obtained and counted. Although the last time police had to seize large quantities of arms from polling places was in 1924, the number of dead who went on casting votes meant an election in Chicago was called Resurrection Day. Yet electioneering was governed by explicit regulations, as Fortune magazine noted in August 1936: “Rule one of this art: never pay a bum his dollar for a full day’s voting in advance. He may drink it up before he has voted the requisite number of times, in which case he will spend the day sleeping it off.” Quaint electoral traditions, abolished by reformers in most other American cities by mid-20th century, made Chicago politicians a hard sell for national office. Obama changed that, his achievement of becoming the first president of African descent less startling than being the first from Chicago.  At his inauguration on January 20 2009, he vowed to “remake America”. His supporters are entitled to ask whether he remade Chicago during his 21 years there, three as a community organiser and 18 as a lawyer and politician. Or did Chicago make him? He saw the city for the first time aged 10, when his grandmother determined the precocious Hawaiian islander should visit the mainland. His memoir, Dreams From My Father, mentions only three images from this three-day stay: the indoor swimming pool at his motel, the elevated train he stood under while shouting as loud as he could and “two shrunken heads” in the Field Museum that struck him as “some sort of cosmic joke”. That was 1970, Richard J Daley’s 16th year as mayor.  Fourteen years later, Obama graduated from Columbia University in New York. He wanted to change the world by organizing communities. His rationale was as idealistic as it was simple, or simplistic: “Change won’t come from the top, I would say. Change will come from a mobilized grass roots. That’s what I’ll do. I’ll organise black folks. At the grass roots. For change.”

 Chicago was the capital of urban activism in America, probably because there was much to be active against. Organisers like Jane Addams and Saul Alinksy aimed at the realistic target of winning concessions from a corrupt power structure, rather than the more problematic goal of eliminating it.

 “Community organising against the political establishment is a fundamental tradition in Chicago,” the left-liberal political consultant and columnist Don Rose told me. With “Another Old White Guy for OBAMA” badge pinned to his jacket, the 78-yearold savant recalled Saul Alinsky’s methods. Rose knew Alinsky, author of the 1946 bestselling Reveille for Radicals. Although the father of Chicago community organising died in 1972 at 63, Rose spoke of him in the present tense, “When Alinsky threatens to take three trainloads of black people to Marshall Field’s department store, he’s not trying to shut down Marshall Field’s, but to get it to hire blacks for various jobs. Or to bring legislation. Or to build a new police station, a new fire station. A kind of petitioning with the threat of force.” Soon after his 1983 graduation from Columbia, Obama applied to work for civil rights and community groups in Chicago. In the absence of any response, he became a researcher for corporate consultancies in New York.Two years later, a community organiser from Chicago approached him and asked what he knew about the place. Obama answered, “Most segregated city in America”. That apparent fact did not deter him from accepting a post in the tough South Side neighbourhoods where blacks had been ignored, abused and exploited for generations. “A week later,” Obama wrote, “I loaded up my car and drove to Chicago.”

The Cook County Democratic Party gave Obama, when he arrived from New York in summer 1985, more instruction on achieving and using power than Saul Alinsky’s manuals. Chicago has been a one-party city since 1931, when the Democrats captured city hall. Their monopoly outlived that of Italy’s Christian Democrats, who ruled in collusion with the Mafia and the Roman Catholic hierarchy in ways the average Chicago ward boss would find familiar, by 34 years. Despite beating the Soviet Communist Party’s 74-year record four years ago, Cook County Democrats have yet to embrace glasnost. It all began with Anton Cermak, an immigrant from Bohemia who, like Obama, had a “funny name”.  “Tony” Cermak graduated from precinct captain to chairman of the Cook County Democratic Party Central Committee in 1928 and took the mayor’s office from the Republican incumbent,William Hale “Big Bill” Thompson, three years later. Thompson, who counted Al Capone among his many friends, had made the mistake of campaigning against Cermak’s foreignness. One slogan went, “I won’t take a back seat to that Bohunk, Chaimock, Chermack or whatever his name is Tony,Tony, where’s your pushcart at?  Can you picture a World’s Fair mayor With a name like that?”….

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