Obama’s Power Problem THE OBAMA WAY: Republicans may enjoy calling the president a typical Chicago politician. But Rick Perlstein argues that Obama isn’t Chicago enough—and that’s why he faces such a tough contest on November 6.

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Over the summer, the Republican Party made a strategic decision: The 2012 presidential election would be, in part, a referendum on politics in Chicago. The city where “politicians quite often end up as felons in jail,” as John Sununu, who served as George H. W. Bush’s chief of staff, recently noted. Where “paying off your friends,” as a spokeswoman for Mitt Romney observed in July, is the coin of the realm. In his keynote speech at August’s Republican National Convention, New Jersey governor Chris Christie put it bluntly: “The president is nothing more than a Chicago ward politician.” Just like Richard J. Daley.

Chicago laughed. Boss Daley and Barack Obama? You could write a treatise on their diametrical oppositions. One was born and died on the same block, among Irish Catholic carbon copies of himself; the other wrote an entire book about how he wasn’t even sure what continent he belonged to. One spent years patiently climbing the political ladder set out for him; the other was famous for jumping the queue. One did politics best in backrooms; the other exemplifies an age when politics is lived on the screen. One could hardly spit out a coherent sentence; the other is the greatest political orator of his generation.

Of course, there is another Chicago political tradition, one that Republicans don’t seem to know exists: the high-minded tradition of reform centered in the city’s Hyde Park neighborhood. “[Obama] represents the ideals of Hyde Park,” said the legendary reformist alderman Leon Despres not long before he died, at the age of 101, in 2009.

Both political traditions—that of the Democratic machine and that of the idealistic reformer—can successfully confer power. But what has become increasingly clear is that Obama has not harnessed the potential flowing from either. Indeed, the president’s biggest problem, come the election on November 6, isn’t that he’s too Chicago. It’s that he’s not Chicago enough.

Barack Obama ended up in Chicago by accident. It just happened to be where a guy, Jerry Kellman, looking to hire an African American community organizer for his South Side group, Calumet Community Religious Conference, liked the cut of his resumé. As David Maraniss writes in his new biography, Barack Obama: The Story, Kellman suspected that this kid from Hawaii named Obama might be part Japanese (Kellman’s wife was Japanese). And so, after Los Angeles and New York City, Chicago became the next stop in Obama’s journey of trying on and discarding ideas and identities, struggling to find the place where he belonged.

He had been here only once before, the summer before his 11th birthday, as a part of a checklist of tourist stops on his first visit to the American mainland. When he arrived in 1985, he had a radical unfamiliarity with, even a fear of, snow. He settled in the South Side neighborhood of Hyde Park—cops called it the Planet, so unmoored it sometimes seemed from the rest of the city—a diverse enclave that includes the University of Chicago campus and its oasis of intellectual transients surrounded by ghettos.

He came to a city at war. Harold Washington’s 1983 election as Chicago’s first black—and first genuinely reformist—mayor had been followed by a veritable secession known as the Council Wars. Led by Edward “Fast Eddie” Vrdolyak, 29 aldermen (28 white, one Hispanic) tried to shut down the fifth floor of City Hall, where the mayor’s office is located, in order to govern the city on their own. A pure product of Chicago’s Democratic machine, Vrydolyak sought to get aldermen credit for delivering the services they were making impossible for Washington to deliver.

That’s classic machine politics: blunt, transactional, materialist—and unashamed of it. “What’s inherently wrong with the word ‘politician,’ ” Richard J. Daley once asked, “if the fellow has devoted his life to holding public office and trying to do something for his people?”

Sometimes that something could be sordid, such as when aldermen extorted bribes to authorize cuts in curbs so cars could access places of business. Then there was the patronage system itself. Committeemen representing Chicago’s 50 aldermanic wards each controlled hundreds of city jobs, a currency for which aldermen were literally “charged.” The 45,000 jobs controlled by the Cook County Democratic Organization were listed on cards at the party office, with the committee member who “owned” each one listed alongside it. You got to “keep” your jobs only if your patronage workers met their share of the expected vote count on Election Day. Whether they actually did any municipal labor hardly mattered. Chicago was the only city in the world, the joke went, where sewer workers could show up to their jobs in white pants.

But machine mayors accomplished plenty of positive things, too. Above all, they were builders. Daley, for example, took office in 1955 during a period of outright municipal depression; the city had lost more than 53,000 manufacturing jobs in the previous seven years. He wrested total control of the City Council, including budgetary control. With it, he built the world’s busiest airport, the world’s biggest convention center, the world’s widest expressway, the biggest block of government buildings outside of Washington, D.C., and more. He did it by putting together savvy bond deals, by finagling permission to increase taxes from the Republican administration in Springfield, and, most of all, by dreaming big dreams and sticking to them—just as he did with his five-year capital improvement plan, announced in 1961, that included some 1,200 separate projects.

Each act of the machine, from the sordid to the soaring, shared a bedrock quality: It was engineered to make the delivery of service as visible to voters as possible, the better to amass political power. “When machine aldermen contacted city agencies for their constituents,” Daley biographers Adam Cohen and Elizabeth Taylor wrote, aldermen demanded written responses so that they “could in turn pass the good news to the voter.” (Daley’s first mayoral opponent’s campaign once boasted, “Television is our precinct captain.” Responded Daley: “Can you ask your television set for a favor?”)

If you were seeking something directly from the mayor, you had to meet with him personally—as if he were Vito Corleone on his daughter’s wedding day—so as to understand exactly from whom the favor derived. (Daley was postpartisan after his own fashion: “Don’t worry if they’re Democrats or Republicans,” he used to say. “Give them service and they’ll become Democrats.”)

Think also of those signs you still see out at O’Hare and Midway that Chicagoans no longer notice but out-of-towners always laugh at—the signs that currently read boldly at the bottom, “Rahm Emanuel, Mayor.” Cohen and Taylor call that the “craft of machine politics”: You have to know who to thank. “Let me put it in a crude way,” the ward boss and Daley mentor Jake Arvey instructed his charge. “Put people under obligation to you.”

Presidents can do that, too. After he signed the law creating Social Security in 1935, Franklin Roosevelt had signs hung in every post office: “A Monthly Check to You for the Rest of Your Life.” Thirty-five years later, Richard Nixon made sure every Social Security check mailed during his reelection campaign included a note saying: “Your Social Security payment has been increased by 20 percent, starting with this month’s check, by a new statute . . . signed into law by President Nixon on July 1, 1972.”

And when George W. Bush passed a tax cut in 2001, he sent it in the form of some 95 million checks in the mail—free money, $300 to $600 per taxpayer, dropping from the sky. He did it again for his 2008 stimulus package. This time folks got checks in amounts up to $1,200, leading to headlines such as this one in USA Today: “Bush: Tax Rebate Checks Are on the Way.”

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Photograph: David Maxwell/epa/Corbis

This article appears in the November 2012 issue of Chicago magazine. Subscribe to Chicago magazine.

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