Until recently, Barack Obama's presidential campaign was premised on the future. The senator from Illinois orated floridly about bringing "change" to the country; a New Political Man, he pledged to soothe the feuds of old and usher in a national reconciliation amid troubled times. With the emergence of divisive figures like Rev. Jeremiah Wright, Obama's longtime friend and acerbically Afro-centric pastor, the focus has shifted to the past, and with good reason. As FrontPageMag.com senior editor Jacob Laksin discovered in his recent reporting from Chicago's South Side, the predominantly black community where Obama launched his political career in the eighties and nineties, Wright may be the best known of Obama's friends and allies, but he may not even be the most controversial. In a series that will appear in FrontPage over the next three days, Laksin explores Obama's ties to the South Side personalities who helped propel him to power, but whose continuing – and reciprocated – friendship with the candidate raises troubling questions about his ability to forge a new political consensus, especially on the fractious issue of race. To evaluate Obama's campaign and its grand promises, readers must first come to know the world of Chicago politics from which he emerged. To read Part I of "Obama's World," click here. -- The Editors

Chicago – On a recent afternoon, the staffers of Chicago’s Third Ward district seemed stumped over a seemingly simple question: where was Dorothy Tillman? First elected in 1985, Tillman worked here for over twenty years, until her defeat last year at the hands of challenger Pat Dowell. Now no one at her former office could say how the ex-alderwoman could be reached.  

The question may seem of merely local interest, but in fact it has a national valence. For Tillman is more than just a marquee name in Chicago politics. She is also known to have a close friendship with the most prominent politician to emerge from the city in recent years, Senator Barack Obama. It is a testament to that friendship that during his 2004 senate run, Tillman, the legendary political boss of Chicago’s largely black Third Ward, was among the politicians whose backing for the fresh-faced former community organizer helped deliver him Chicago’s predominantly black wards, where Obama won more than 90 percent of the vote – no small achievement for a novice politician struggling to emerge from the shadow of iconic South Side figures like ex-Black Panther Rep. Bobby Rush, who defeated Obama in a 2000 Congressional race. More recently, Obama reaffirmed his relationship with Tillman when, to the dismay of much grassroots opposition, he endorsed her last year in an ultimately unsuccessful quest to retain her post as assemblywoman for the Third Ward.

And yet that defeat, which dramatically reduced Tillman’s profile, also marked a small victory for Obama, if only in terms of public relations. Indeed, no one benefits more from Tillman’s sudden anonymity than the senator. As he struggles to broaden his appeal across the country, especially among the white, working-class voters who remain skeptical of his candidacy, the last thing Obama needs is for further scrutiny to be directed at the circle of controversial supporters and political allies in Chicago who aided his rise from lowly activist to senator to would-be president of the United States. A case in point is Obama’s longtime friendship with his outspokenly anti-American pastor, the Reverend Jeremiah Wright, which precipitated a damaging political backlash against his campaign that has yet to subside.

Dorothy Tillman is another such figure. A veteran of Chicago’s combative politics, Tillman possesses one of the city’s more outsize personalities. Best known for her collection of garish, broad-brimmed hats and her unstable behavior – she once brandished a handgun at a City Council meeting –Tillman also has gained fame or infamy, depending on whom one consults, for her revealed record of municipal corruption, her uncompromising views on race, and her professed anti-Americanism. It is precisely those views that underlie her support for black empowerment, an ideological obsession that, as in the case of Jeremiah Wright, sometimes has shaded into overt racism. Meanwhile, Tillman’s preferred causes – prominent among them her championing of reparations for slavery – place her well outside the mainstream of the American electorate even as they endear her to many in Chicago’s black community.

Now, as Obama makes his pitch to the American people – a pitch resting largely on the biracial candidate’s presumed ability to resolve racial disputes and to distance himself from the corrupt ways of establishment Washington – his ties to politicians like Dorothy Tillman raise troubling questions about his judgment, his independence, and his ability to bring about the “change” that has been the rhetorical cornerstone of his presidential campaign.

Tillman’s political résumé has a certain heft.  She began her career in her native Alabama, where at the age of 16 she joined the civil-rights movement and worked as an organizer with Dr. Martin Luther King’s Southern Christian Leadership Conference (SCLC). When King decided to shift his operations from the South to Chicago in 1965, Tillman was sent to the city to lay the groundwork for his arrival.

She struggled with this charge. The black and white moral situation in the segregated South, which made organizing relatively easy (if physically dangerous) there dissolved into gray ambiguity in the north, where racism was more subtle and where a local black power structure was invested in the status quo. The confrontational style of Southern activists like Tillman ill-suited Chicago’s black residents, and the reception she received was not a warm one. “Blacks in Chicago actually allowed other blacks to go on television and say they were not wanted in Chicago,” Tillman would later complain. “As a matter of fact, we could not find a church pastored by a black minister…that would give the SCLC office space. Therefore, we ended up with a white pastor.” Outraged, Tillman dismissed Chicago’s blacks as “Uncle Toms.”

Primarily to blame for the weakness, as she saw it, of the black community, was Chicago’s machine politics. In her judgment, it had made blacks dependent on the patronage of the city’s white Democratic establishment. So debilitating was this dependence, Tillman charged, that “[b]lacks in this city were worse off than any plantation down South.”

Tillman, along with more radical elements in the black community, settled on a single solution: What was needed was a politics of black empowerment that would build up an independent black political machine to counter the dominant white one that had coopted black leadership since the turn of the century.

Tillman would get her chance to realize this vision in the 1984. When elected alderman Tyrone Kenner was forced out of the city council after being convicted for extortion (he had been collecting commissions for “selling” city jobs), then-mayor Harold Washington tapped Tillman to fill the vacancy. Despite initial resistance – one alderman reportedly refused to support the appointment because Tillman had called him an obscene name – she won the backing of the council and the voters. For the next 23 years, Tillman would represent the Third Ward in the City Council. In that time, her tenure would come to be distinguished less by any significant accomplishments than by Tillman’s advocacy of some decidedly sectarian causes.

Of these the most polarizing was reparations for slavery. It does not exaggerate her role in the reparations movement to say that during her time in elected politics Tillman was its leading – and arguably most acerbic – proponent. In 2001, for instance, Tillman hosted the first ever “National Reparations Convention for African-American Descendants of African Slaves” in Chicago. Under Tillman’s direction, the convention drafted a “national plan” that would have compelled the federal government and American corporations to provide reparations to the descendants of American slaves.

Never a serious contender for adoption into law, the plan nevertheless cast a spotlight on Tillman’s radical views on race and her rabid anti-Americanism. “America,” Tillman has said, “is one of the cruelest nations in the world when it comes to black folks.” Only reparations could atone for this cruelty. “America would not be the America it is today without slavery,” Tillman has claimed.

Nor had the country made any progress since the slave era, in her opinion. Slavery, Tillman insisted, had “put the freed slaves and their descendants at a disadvantage that will never be overcome without reparations” – a statement that surely would have come as a surprise to the nearly fifty percent of black Americans who today own their own homes and who have made steady gains in the American economy in recent decades. But evidence of expanding opportunity and growing prosperity for black Americans failed to impress Tillman. Declaring that “America owes blacks a debt,” she pledged to accept nothing less than full reparations as just recompense.

Extreme as it is by national standards, the reparations issue nevertheless enjoys broad support in communities like Chicago’s South Side. That Tillman adopted it as her signature cause only improved her political fortunes. It is telling that in 1987, when Obama was in the early stages of his career as a community organizer, Tillman carried the Third Ward with nearly 80 percent of the vote. Later, when Obama courted the black establishment to support his political ambitions, he would directly benefit from the clout that politicians like Tillman had amassed by championing racially divisive but locally popular causes.

And it is here that Obama’s political roots on the South Side become particularly problematic. It would be sufficiently embarrassing for Obama to be associated with the leader of an unabashedly racial cause that alienates most Americans. But ever worse for the candidate’s ambitions to inspire the country is that Tillman is not the only member of Obama’s support group in Chicago to have taken up the cause of reparations. In June of 2007, the chapter of the National Coalition of Blacks for Reparations (NCOBRA) in America held its annual conference in Philadelphia. Consistent with its mission to win reparations for the “genocidal war against Africans” created by the slave trade and its alleged “continuing vestiges,” NCOBRA selected a keynote speaker who shared its extreme views. That speaker was none other than Reverend Jeremiah Wright.

It’s impossible to understand the popularity of reparations in communities like Chicago’s South Side without first understanding the worldview from which the spring. Unmistakably racial, it is a view that sees blacks as prisoners of American history, incapable of improving their lot without the aid of the federal government and the crutch of black solidarity.

No one speaks for that view with more determination than Dorothy Tillman. In 2001, the alderwoman touched off a citywide scandal when she made a racial scene at a restaurant. While attending a political reception at Chicago’s posh Palmer House Hilton hotel, Tillman reportedly demanded that she be served by only black waiters. Two white waiters later brought suit against Tillman, charging that she had them removed from the reception. Even Chicago Mayor Richard Daley was moved to reproach Tillman, chiding that “I can't say to you that, because you're black, white, Hispanic, Asian or a woman or male or your sexual orientation and I don't like you, you have no right to serve me. That's not what we stand for.”

In fact, it was what Tillman stood for. In the aftermath of the scandal, the alderwoman seemed genuinely puzzled what all the fuss was about. "It is not personal against anybody. I am just pro-my people,” she explained, adding: “Being pro-black is not being pro-racist.”

In the black community, meanwhile, Tillman was praised for her defiance. Jay Thomas Willis, a columnist for Louis Farrakhan’s newspaper, The Final Call, hailed Tillman for her commitment to racial politics. “I admire Mrs. Tillman for speaking out on the issues and putting her money where her mouth is,” he wrote. As for complaints of racism, these were not to be taken seriously: “Whenever blacks talk about getting what they want, whites call it reverse discrimination.”

It comes as no surprise that Tillman’s unapologetic commitment to racial politics also has won her the approval of one of the country’s leading racists: her friend and fellow reparations advocate Louis Farrakhan. In 2005, Tillman was an honored guest at a lecture by Farrakhan, and returned the compliment by praising the minister as a patron of the community. “We have always supported the minister when others were running away,” Tillman gushed. “I am thankful for the role for the role that we played.”

Considering his campaign’s promise to do-away with divisive politics, one might think that Obama would jump at the chance to distance himself from race-centric supporters like Tillman. So it is revealing of the candidate’s lingering loyalties to radical black leaders like Tillman, and a sign of his deference to the popular prejudices of the community she represents, that he has failed forcefully to repudiate the politics of racial resentment that continue to thrive on Chicago’s South Side. 

Instead, Obama has staked out positions that might be characterized as evasive. That was most apparent on the fraught question of reparations. When asked by CNN’s Anderson Cooper last July where he stood on reparations, Obama gave a rambling response in which he backed unspecified “investments” in education. And though he ultimately declined to join Dennis Kucinich in openly supporting reparations, his equivocal answer allowed him to please both the majority of the country that opposes them and those elements of the black community for whom they remain a cherished cause. As a demonstration of Obama’s ability to appease different constituencies, it was an impressive performance. But those seeking real leadership from the candidate, not least on the fractious question of race, would have been disappointed. 

Obama’s relationship with Tillman undermines more than his promise to forge a national consensus on race. It also threatens his pledge to transcend the cynical corruption that, as he tells it, has made politics a dirty word. Indeed, it would be difficult to find a better example of dirty politics-as-usual than the career of Dorothy Tillman.

It was not supposed to be that way. Not least because she was replacing a disgraced public official, Tillman’s appointment to City Hall in 1984 was hailed as part of a broader effort to renovate the city’s black communities. “When I first came here, I inherited a very corrupt, dirty, nasty ward, and we came in and launched a clean-up campaign,” Tillman would later recall.

But the campaign foundered from the start. Premised on two conflicting aims – to eliminate corruption on the one hand, to promote black empowerment at all costs on the other – Tillman’s tenure often fell short of the grand hopes with which it began. Before long, critics took to charging that Tillman abused her authority as alderwoman in order to secure city funds for development projects. While community groups had their requests denied, Tillman seemed always to have her hands on the city’s purse strings.

Allegations of this sort came to a head in 2006. A local newspaper, Lakefront Outlook, decided to launch an investigation into Tillman’s financial books. What it discovered was a pattern of suspicious financial irregularities stemming from her pet project, a taxpayer-funded facility called the Harold Washington Center. According to the paper’s findings, the center, built directly across the street from Tillman’s war office, was marred by tax violations, its operations no more improved by the fact that Tillman was engaging in blatant nepotism, hiring family members to staff the financially troubled institution. Thus, one of Tillman’s daughters ran both the center and the catering service that supplied it.

On the strength of these and other revelations, Tillman’s challenger Pat Dowell, a former deputy executive in Chicago’s Department of Planning and Development, was able to paint Tillman as being “out of touch with the people in the community.” With her penchant for playing the race card – Tillman had long adopted the tactic of assailing the mere presence political opposition as evidence of “racism” – rendered ineffective against her black opponent, Tillman was voted out of office.

Tillman’s loss came despite the support of most the city’s black community, and her most prominent supporter was Senator Obama. Explaining that Tillman was “a very early supporter of my campaign” for the Senate, Obama endorsed Tillman in the Third Ward race.

It was in many ways a strange move. In light of Tillman’s record of corruption and her comparatively thin record of achievement, Obama’s support for the incumbent struck many as a betrayal of the political promises, especially ethics reform, that had gotten Obama elected in 2004. James Shapiro, the state chairman for the Independent Voters of Illinois-Independent Precinct Organization, noted that Obama’s support for Tillman showed a preference for “political expedience” over principle. Media coverage was similarly critical. The Chicago Tribune suggested that Obama’s endorsement “reflects his deference to Chicago's established political order and runs counter to his public calls for clean government.”

For his part, Obama was unrepentant. There was no “conflict” between his support for ethical reform generally and his support for one of the city’s most corrupt politicians, he said. And while the defense strained credulity, it demonstrated the debt that Obama still owed to politicians like Tillman.

That debt is well established. During his 2004 Senate run, Obama faced a powerful challenge from his opponent, multimillionaire businessman Blair Hull. With a $29 million campaign war chest that he used to court the city’s black political class, Hull was heavily favored to win. Obama’s endorsement by established black politicians like Tillman gave him a local credibility he lacked and, along with unconfirmed but scandalous claims that Hull had abused his ex-wife, helped lift the novice politician to an upset.

With his endorsement of Tillman in 2006, in the face of grassroots opposition, Obama repaid the favor. If doing so violated the high-minded rhetoric that has driven his campaign for president, it was nevertheless a price that Obama was willing to pay.

Barack Obama’s defenders protest that their candidate does not share the more militant racial views of his allies on the South Side. This is likely true, but it is irrelevant. As a young organizer in the 1980s, Obama sincerely sought to improve the lot of blacks in troubled communities. In doing so, however, he assembled a community of vocal supporters whose political views, especially but not solely on matters of race, are an affront to the national reconciliation that the Illinois senator has said he hopes to achieve as president. 

The story of Obama’s meteoric ascent from Chicago’s streets to the national stage is, in the end, the classic story of the Faustian bargain. To fuel his rise up the political ladder, Obama needed to downplay both his history, as the son of a white middle-class mother raised by his white grandparents, and his résumé, as the fortunate son who made his way from exclusive Hawaii private schools to the hallowed halls of Columbia and Harvard. In the world of Chicago’s South Side, Obama found the answer in his alliance with radical religious figures like Rev. Wright and his political counterpart in Dorothy Tillman. The fact that he repaid their support with friendship and, when the opportunity arose, political backing, may be a credit to Obama’s integrity. But it is a damning indictment of the kind of politics – anti-ideological, non-partisan, post-racial – that he now claims to represent.