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 couldn’t be further from the way that Barack Obama does business. As part of his first stimulus bill, for example, President Obama passed a massive tax cut, too, amounting to an average of $400 for 95 percent of taxpayers in the work force. But he didn’t do it the way that Bush—or a Chicago machine pol—would have. Instead, Obama’s gift came dribbled out over the course of a year in practically invisible adjustments to citizens’ paychecks. The result: People still talk about the “Bush tax cuts,” but a 2010 CBS/New York Times poll found that only 12 percent of voters believed that their taxes had gone down under Obama. By a ratio of 2 to 1, respondents actually thought their taxes had gone up.

That sure ain’t the Chicago way.

Further consider Obama’s signature accomplishment: health care reform. Its key provisions do not go into effect until 2014, two years after this month’s presidential election—a decision that seems calculated not to seed voter gratitude. Obama has even refused to put resources in voters’ hands when the money has already been appropriated. For example, only $3 billion of the $75 billion earmarked for the foreclosure-fighting Home Affordable Modification Program has been spent. (The reason, according to Neil Barofsky, the former inspector general for the Troubled Asset Relief Program, under whose auspices HAMP was run: The intention was not to deliver a service to voters but to “foam the runway” for crashing banks, helping them absorb housing-related investment losses.)

Obama hasn’t been much of a builder, either—or much of a salesman for what he has built. Rather than ramping up big public works projects à la Daley or Roosevelt—which could have helped millions of people find jobs—he complained of a dearth of “shovel-ready” projects to fund. He actually ratcheted down the public works component of the stimulus, against the advice of a faction of White House economists who argued that much higher spending was required to get the economy back on track.

In contrast to the Republican record, Obama has been more reluctant to expand government. In the first three and a half years of George W. Bush’s presidency, public sector employment at all levels grew by 800,000 jobs, but in the Obama years the public sector has lost about 600,000 jobs—in part because he limited federal aid to states and municipalities in the stimulus. (In fact growth in government spending under Obama has been less than under any president since Dwight D. Eisenhower—including even Ronald Reagan.)

Meanwhile, Bush also used his direct power to increase federal political appointees by 12.5 percent, and also politicized previously ideologically neutral jobs like United States attorneys—in the Chicago way, you could say. Obama, on the other hand, has been notably reticent to use his power of appointment to put his political stamp on the government bureaucracy.

Obama seems to think that if he shows himself to be a trustworthy steward of the public purse, Republicans will respect him and the voting public will be grateful. It hasn’t worked. An April poll by The Washington Post and ABC News found that 54 percent of voters believed that Romney would deal better with the budget deficit, compared with 37 percent who thought Obama would. As for the notion of earning Republicans’ respect: What would Daley say about that?

Absurdly, certain Republicans like to quote the classic movie line about the “Chicago way” from The Untouchables when referring to the Obama White House: “He pulls a knife, you pull a gun; he sends one of yours to the hospital, you send one of his to the morgue.” It refers to the uniquely cutthroat way that Chicagoans allegedly deal with the opposition. A more accurate description of the Chicago way was uttered by the man who invented the Democratic machine, Anton Cermak. “I want your cooperation,” the mayor told his aldermen, “and if I cannot have it, I will go ahead anyway.”

That’s definitely not President Obama’s management modus operandi. Granted, Congress is not the City Council. For one thing, it has members of both political parties. For another, a modern president’s ability to cut off legislators’ access to services their constituents need is severely limited.

But even when Obama had majorities in both the House and the Senate, he rarely behaved like a political boss. The best example was the way he launched his health care proposal. Instead of presenting a legislative package as a fait accompli for the bodies to vote on—as Mayor Emanuel did with his budget and infrastructure bank—he initially farmed out the drafting of the proposal to a bipartisan “Gang of Six.” He thought he could achieve more with cooperation. He did so even though the Senate’s minority leader, Mitch McConnell, had openly proclaimed, “The single most important thing we want to achieve is for President Obama to be a one-term president.”

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Photograph: Pete Souza/Official White House Photo

Obama reaches out in good faith to negotiating partners who have no intention of offering good faith in return. He has, after all, pledged his presidency to transcending the old tit-for-tat politics of “us versus them” and pledged himself to a better, nobler version of government. And that’s where Chicago’s second political tradition, the Hyde Park tradition of reform, comes in.

A distrust of the dirtier aspects of power is its calling card. Consider one of Obama’s old Hyde Park mentors. Leon Despres was a warrior against the brute transactional efficiencies of pay-to-play politics from his initial election to the City Council in 1955—the year Daley became mayor. His first successful ordinance was a ban on selling curb cuts, and he went on to distinguish himself as the city’s moral light in crusade after crusade. Hyde Park rewarded him by repeatedly returning him to City Hall. But Despres so mistrusted power that he gladly gave it up. In 1975, at the height of his influence and the nadir of Daley’s, he surrendered his City Council seat.

Another Hyde Park reformer provided the inspiration that Obama says attracted him to Chicago in the first place: Harold Washington. Washington was a complicated man with a complicated legacy, and because he suffered a fatal heart attack months after his 1987 reelection, we’ll never know whether he could have truly transformed the institutional framework of the city. One fact, though, is undeniable: During his four years as mayor, he managed to handle his recalcitrant political foes aggressively while remaining true to his ideals.

And their recalcitrance was epic. “I won’t work a day for that man,” announced Richard Brzeczek, the police superintendent, who resigned two days after Washington took office. The black power brokers who had helped get Washington elected knew just how the mayor should respond: by filling vacancies like these with “his own,” using patronage payback to shut out those who had held blacks in check for so long. Washington refused. “No one, but no one, in this city is free from the fairness of our administration,” he said. “We’ll find you and be fair to you wherever you are.”

He meant it. Washington was the first mayor to comply fully with a federal court order to end political patronage jobs, and he imposed a cap on campaign contributions from those doing business with the city. His less idealistic black backers were agonized. “Why change the rules,” Alderman William Beavers wanted to know, “just when we’re getting into the game?”

Washington stuck to his guns, even though all it would have taken to jump-start city government was to cut a deal with the Vrdolyak machine that had so successfully shut things down. The approach worked. Four years later, he won reelection with wider margins in the primary and general elections than he had in 1983.

It was hardly for his record of accomplishments: Thanks to the Council Wars, Washington hadn’t really been able to govern at all. He won by taking unpopular positions and becoming popular for it. Machine stalwarts such as Richard Mell wound up defecting to his side, for he had the power—power that he had built the reformer’s way. Harold Washington showed, for a brief, shimmering moment, something that all scholars of truly transformational figures know: that putting moral excellence on dramatic display, adversarially, in the face of defiant opposition, is another way to store and deploy political power.

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Photography: (Daley) AP photo file; (Despres) Chicago Tribune; (Obama) Nikki Kahn/The Washington Post via Getty Images

Those dreams burned bright in late 2007, when Obama, then a U.S. senator, gave a speech to inspire his Iowa caucus activists. He consecrated them in the name of “a band of unlikely patriots who overthrew the tyranny of a king . . . the legacy of abolitionists . . . those women’s suffragists and freedom riders who stood up for justice.” He told them: “I hope you remember this as a moment when your own story and the American story came together, that moment when history bent once more in the direction of justice.”

Words like this once stirred political reformers like Despres, who, you’ll recall, told this magazine a few months after Obama’s inauguration: “[Obama] represents the ideals of Hyde Park.” But does he still?

That’s what I asked another of Obama’s Hyde Park mentors, Quentin Young. A physician and an outspoken advocate for single-payer health care, Young was deeply stung when Senator Obama abandoned the fight for single-payer coverage—even after he admitted it was the best approach to fix a broken system—and when, early on, President Obama threw in the towel on a “public option” in his health care plan. To my question about Despres’s quote, Young responded: “It’s a wonderful compliment from a wonderful man. But I don’t think it’s accurate.”

The Hyde Park dream is to leverage moral power into conventional political power and, in turn, to leverage that into the most lasting power of all: the power, as Obama said that day in Iowa, to bend history, to transform institutions that had previously been seen as intractable. That’s the promise that many disillusioned Obamaites feel he has squandered. Even among his supporters, few now see Obama as a torchbearer of moral transcendence. Critics say that his presidency has been not just cloutless but morally centerless. And that ain’t the Hyde Park way.

Those who worked for him hardest during that historic 2008 run can now recite their disappointments chapter and verse. Al Gore, for instance, who threw a green inaugural ball for Obama, has blasted the president for having “simply not made the case for action” on global warming.

Others say that Obama has broken his promise to create the most open government in history. Instead, it’s been one of the most tightly controlled. For instance, the White House demands all quotations from even mid-level officials that appear in the media be approved in advance. And many bureaucrats fighting for transparency have found their lives hell. Consider what has happened to bureaucrats like Thomas Drake, who fought to tell the truth. A National Security Agency whistleblower who in 2010 revealed details showing a new surveillance program to be a costly failure, Drake found himself charged under the 1917 Espionage Act, which, in essence, deems those convicted under it to be enemies of the United States. The felony charges were dropped after the case was widely publicized. Still, the Obama administration has charged more whistleblowers under the act—six in all—than all previous administrations combined.

Then there’s the president’s unilateral authorization of drone strikes, even against those who are American citizens. Jimmy Carter, another president to win a Nobel Peace Prize, cited drone strikes and their record of killing innocent civilians in a June New York Times op-ed article arguing that Obama has violated 10 of the 30 articles of the United Nations Universal Declaration of Human Rights. “Our country,” wrote Carter, “can no longer speak with moral authority on these critical issues.”

Whatever one thinks of these robot killings from above as a military tactic or a humanitarian issue, the Hyde Park president’s response to questions about the strikes has hardly fulfilled his promise of transparency. When he was asked in September by a TV reporter in Toledo, Ohio, about how he justified having a “kill list,” Obama’s answer was downright Orwellian. The reporter was “basing this on reports in the news that have never been confirmed by me,” he said.

When it comes to economic policy, some critics say that the Chicago tradition Obama honors most is the Chicago school of economics. Take his first public remarks after JPMorgan Chase revealed in the spring that it had lost an estimated $2 billion trading in derivatives meant to be hedges against such losses. He called JPMorgan “one of the best-managed banks there is” and the firm’s chief executive officer, Jamie Dimon, “one of the smartest bankers we got.” Estimates of losses were later revised upward to $7 billion.

If you have built your appeal on moral power, it’s hard to be taken seriously once the world sees you as having feet of clay—unless, that is, you can successfully revert to that other, entirely different way of getting things done: the way of clout. Neither the brass-knuckled Chicago pol right-wing fantasy nor the Hyde Park reformer of liberal dreams, Obama finds himself in a weird in-between region where he derives no benefit from either side but somehow absorbs the demerits of both.

Obama’s retreat from principle has the same result as his lack of mastery of the less corrupt lessons of the old machine: It leaves power on the table. And if he loses to Romney on November 6, his failure to adhere to either one of Chicago’s two mighty political traditions will be the reason.