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From Chicago’s South Side to the Senate: The political education of Barack Obama

By Carol Eisenberg

May 23, 2008 at 8:24am

The magnet that drew a 23-year-old idealist named Barack Obama to Chicago was Harold Washington, Chicago’s first African-American mayor.

As a young man, Obama idolized the politician who had vanquished the Chicago machine and two of its most powerful players, then-Mayor Jane Byrne and future-mayor Richard M. Daley, after they split the white vote in a three-way race in 1983. The young Obama wrote the new mayor asking for a job, but heard nothing back, so he signed on as a community organizer on Chicago’s South side, arriving in his beat-up blue Honda in June, 1985. (Washington died of a heart attack in office, several months after winning re-election, in November 1987.)

As a newcomer, Obama aligned himself with the reformers. He put down roots in Hyde Park, an integrated neighborhood with a history of electing independent-minded politicians that was home to the late Washington, as well as to Carol Moseley Braun, Jesse Jackson Jr. and the University of Chicago.

More than two decades later, Obama-the-presidential-aspirant had come to have a far more nuanced and pragmatic view of Chicago’s political establishment. In 2007, he endorsed then-Mayor Daley, son of the late party boss of the same name, who returned the favor when Obama declared for the Democratic presidential nomination. By then, Obama had mastered the skill of mixing an idealist’s message with a politician’s tactical approach to alliances.

Powerful mentors guide him

“I think I have done a good job in rising politically in this
environment without being entangled in some of the traditional
problems of Chicago politics.”

~ Barack Obama

Obama’s education in the bare-knuckled and often tribal politics of Chicago says much about his ambition, as well as his ability to cultivate powerful mentors, from an aging liberal Jewish judge in Chicago named Abner Mikva, who knew all the byways of power, to a gravelly-voiced, black sewer inspector-turned-political-leader in Springfield named Emil Jones Jr., who helped Obama navigate the capitol’s byzantine politics.

Over the years, Obama traded his stiff, Ivy League delivery style for the cadences of a black preacher, and built coalitions by pivoting from his left-leaning Hyde Park base to appeal to more centrist constituencies.

And even as he touted good government causes, he cultivated an insider’s ties to important parts of the establishment, from the power brokers in the powerful Cook County Democratic organization, to the city’s leading black politicians: His wife, Michelle, worked for the Daley administration in the early 1990s. And many of his closest advisers, among them, David Axelrod and Valerie B. Jarrett, are allied with Daley as onetime appointees and advisers.

“I think I have done a good job in rising politically in this environment without being entangled in some of the traditional problems of Chicago politics,” Obama told reporters and editors at a Tribune editorial board meeting.

Not everyone is convinced.

“There are no virgins in politics, let alone in Chicago politics,” asserts Fred Siegel, author of “The Prince of the City: Giuliani, New York and the Genius of American Life,” and a professor at New York’s Cooper Union.

Siegel cites Obama’s endorsements of Daley, as well as of former Chicago alderman Dorothy Tillman, perhaps best known for taking a pistol from her purse and brandishing it at a City Council meeting, and who was ultimately rejected by her district the face of charges of corruption and graft. Reformers were also stunned in 2006, when Obama endorsed Todd Stroger, son of longtime Cook County Board president John Stroger and the ward bosses’ pick to assume his father’s mantle after the elder Stroger suffered a stroke.

“Obama may not have come out of that world of the Chicago machine, but he’s been a functional ally,” Siegel said. “The idea that he’s a reformer is simply bizarre.”

Looking for ways to make the tent as large as possible

Obama’s supporters contend that he has consistently championed good-government and ethics reform even as he built alliances to get things done - without allowing himself to be defined or limited by others’ agendas.

“There are some people who say he’s not strong enough on this or that, that he’s wishy-washy, that he’s trying to have it both ways,” Mikva, a former state legislator, congressman, judge and counsel to President Bill Clinton, told the New York Times. “But he’s not looking for how to exclude the people who don’t agree with him. He’s looking for ways to make the tent as large as possible.”

Obama’s earliest involvements in Chicago gave him entree to both the Establishment and progressive political worlds, which, like almost everything else in Chicago overlap. He married Chicago native Michelle Robinson, a Princeton and Harvard-educated lawyer whose father had volunteered as a Democratic precinct captain on the South Side, and whose childhood friend, Santita, is a daughter of the Rev. Jesse Jackson whose Rainbow/PUSH Coalition, a civil rights group, still operates from the city’s South Side.

After his stint as a community organizer, followed by law school, Obama returned to Chicago in 1992. Admirers say it is testament to his idealism that he delayed going to work for a law firm to direct a voter registration campaign targeting low-income blacks. Illinois Project Vote, as it was called, registered more than 100,000 new voters for the 1992 presidential election, boosting both Bill Clinton’s tallies in Illinois, as well as Moseley Braun’s campaign to become the first black woman elected to the U.S. Senate.

Some of those he enlisted in the vote effort would become long-term allies, among them John R. Schmidt, a former chief of staff to Daley and associate attorney general, and John W. Rogers Jr., a young black money manager and college friend of his brother-in-law’s.

“He really did it, and he let other people take all the credit,” Schmidt told the Washington Post. “The people standing up at the press conferences were Jesse Jackson and Bobby Rush and I don’t know who else. Barack was off to the side, and only the people who were close to it knew he had done all the work.”

Law firm job a political stepping stone

“There are no virgins in politics, let alone in Chicago politics.”

~ Fred Siegel, author of The Prince of the City

Obama had already turned down offers to work for white-shoe law firms, and after the six-month voters’ drive, he went to Davis Miner Barnhill & Galland, as it was then called, a firm touted in progressive circles for its work on voting rights and housing equality. For Obama, a large part of the appeal was senior partner Judson Miner, a former counsel to Harold Washington.

“During the course of our talking, it came out that people who knew he was having lunch with me were trying to convince him that this was the worst place for him to go,” Miner told the New York Times. “He shared this with me – he was amused. This isn’t where you land if you want to curry favor with the Democratic power structure.”

But the job was the perfect political stepping stone for an aspirant from Hyde Park. Miner introduced him to the key players in the coalition that had elected Washington, many of whom became Obama supporters. When Obama ran for Illinois Senate a few years later, Miner supported him.

But other alliances forged at Miner have come back to haunt him. Besides working on voting rights at Miner’s firm, Obama did work on low-income housing projects involving developer and restaurant chain owner Antoin “Tony” Rezko, who would become one of his first financial contributors. Rezko, who liked to accumulate politicians like fast-food restaurants, is on trial for using his connections to state boards to demand kickbacks from companies that wanted to do business with the state – a case with no connection to Obama.

Entanglement with Rezko

Obama has taken heat, however, for getting help from Rezko to purchase his home. In 2005, he bought a mock-Georgian Chicago mansion for $1.65 million - $300,000 below the original price - on the same day that Rezko’s wife, Rita, purchased the adjoining garden from the same sellers for the full asking price. Later, Rita Rezko sold the Obamas a 10-foot strip of land that expanded their yard. Obama has denied any impropriety, saying the seller insisted on selling the two parcels on the same date. But he acknowledged the deal looked bad and called it a “boneheaded mistake.”

During the same years he worked for Miner’s firm, Obama also taught part-time at the University of Chicago Law School, where he made other political contacts. That’s where he befriended Mikva, the former judge who would ask his longtime golfing partner, Emil Jones Jr., the powerful Democratic leader in the Illinois Senate, to look after Obama after he was elected to the state Senate in 1996.

Jones is described in David Mendell’s biography, “Obama: From Promise to Power,” as “a street-tough African American who had risen from Chicago sewer inspector to enter the corridors of power in Springfield.” After Obama’s election to the Illinois Senate, an unlikely friendship developed between the two, with Jones becoming almost like a surrogate father to the younger man. “I am blessed to be his godfather and he feels like a son to me,” he told Mendell.

Indeed, Jones would become Obama’s kingmaker. For six of the seven years Obama spent in Springfield, the Republicans controlled the General Assembly, and like other Democrats, Obama had only limited success in passing legislation, among other items, a rare ethics law in a state known for government corruption.

But when the Democrats achieved a sweep in 2002, and Jones became majority leader, he anointed Obama as the go-to guy on virtually every high-profile piece of legislation – a record that set him up for his run for U.S Senate.

Ill-fated primary against Bobby Rush

Still, Obama was restless in Springfield. In 2000, he had disregarded the advice of his political friends and mounted a primary challenge to incumbent Congressman Bobby Rush, a former alderman, four-term incumbent and onetime leader of the Illinois Black Panthers with deep roots in the South Side African-American community.

Rush routed him getting 61 percent of the vote to Obama’s 30 percent. Sounding themes later hammered by New York Sen. Hillary Clinton, Rush portrayed him as an elite Ivy Leaguer who was out of touch with those he was seeking to represent. “He went to Harvard and became an educated fool,” Rush told the Chicago Reader.

Analysts said that that trouncing was a humiliating course in political coalition-building 101 for Obama – and that he learned the lesson well. After the debacle, he began to reach out to players from whom he had previously remained aloof, from some key African American leaders to party regulars.

“He didn’t seem to get bitter,” William Daley, the mayor’s brother, told the Washington Post. “He didn’t turn on people. He engaged people more and worked on it.”

Only a few years later, when Obama announced for the U.S. Senate, he had a far more sophisticated game plan. He asked his friend Martin Nesbitt to set up a meeting with businesswoman and billionaire Penny Pritzker, with whom he worked as a vice president of Pritzker Realty Group. Obama and his wife would persuade her to oversee fund-raising for his next campaign.

Expanding his political team

With Pritzker on board, he expanded his base of contributors beyond the wealthy black entrepeneurs and lakefront liberals who had supported him the past to include a much larger pool of influential Democrats and philanthropists. Among them were Newton Minow, senior counsel at Sidley Austin LLP, where Obama had interned and who had advised Sen. Adlai Stevenson and Presidents John F. Kennedy and Lyndon Johnson; James Crown and members of the wealthy Crown family; and John Bryan, then chief executive of the Sara Lee Corporation.

Obama also appealed for help from Axelrod, a well-connected political consultant who had worked for Harold Washington and who was now close to Mayor Daley. Initially, Axelrod discouraged him from making the run, saying that although he was a “terrific talent,” he should wait until Daley retired and then run for mayor, according to Mandell’s book.

Eventually, Axelrod came on board, persuaded in part by Bettylu Saltzman, the daughter of the late developer Philip Lutznick and a liberal stalwart who became close with him while running the Chicago office of the late Sen. Paul Simon.

Speaking out against Iraq War

In October, 2002, Saltzman was organizing an antiwar rally and asked Obama if he would speak. About to announce his bid for the U.S Senate, Obama did not say yes right away. Ultimately, he appeared, giving what was arguably the most important speech of his political career up until that time.

Saying he was not opposed to all wars, only “dumb wars,” Obama warned that a U.S. occupation of Iraq would be of “undetermined length, at undetermined cost, with undetermined consequences.” The speech, which would prove prescient, would help define him not just for the U.S. Senate race, but later in the crowded field of contenders for the Democratic nomination for president.

By the time he announced his candidacy for the U.S. Senate a few months later, Axelrod had committed to work with him. Obama had also gotten a group of about a dozen established Democrats, including Jones, Jesse Jackson Jr. and U.S. Rep. Danny Davis to back him.

In 2007, when he announced his decision to go after the Democratic nomination for president, that same coalition would step up to the plate - this time with Daley and the Cook County Democratic Party added to the mix.

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