By Chris Lane
By Jeff Balke
By Aaron Reiss
By Angelica Leicht
By Dianna Wray
By Aaron Reiss
By Camilo Smith
By Craig Malisow
"Obama can't bring those issues up if he wants to be elected," Lucas says. "And that's the travesty of the situation that we find ourselves in as African-Americans."
In the presidential campaign, Obama has been criticized for a shady land deal and other past ties to Tony Rezko, the Chicago real estate developer and ubiquitous political donor who now faces federal charges of attempted extortion and money laundering.
In a debate held last month before the South Carolina primary, Hillary Clinton charged that Obama had legally represented Rezko "in his slum landlord business in inner-city Chicago." The issue was turned back on her a few days later when an old picture of a smiling Clinton posing with Rezko surfaced on Drudge Report.
Though it didn't make national news, Obama inflamed many residents in his old state Senate district last March when he endorsed controversial Chicago alderman Dorothy Tillman in a runoff election.
Flamboyant and unpredictable, Tillman is perhaps best known for once pulling a pistol from her purse and brandishing it around at a city council meeting. The ward she represented for 22 years, which included historic Bronzeville, comprised the city's largest concentration of vacant lots.
Just three months before Obama made his endorsement, the Lakefront Outlook community newspaper ran a three-part investigative series exposing flagrant cronyism and possible tax-law violations that centered on Tillman and her biggest pet project, a taxpayer-funded cultural center built across the street from her ward office that had been hemorrhaging money since its inception.
The series won a national George Polk Award, among the most coveted prizes in journalism. Not bad for a 12-page rag with a circulation of 12,000 and no Web site. I had already left the Outlook and had nothing to do with the project.
In the end, Tillman lost the election despite Obama's endorsement, which critics said countered his calls for clean government. Obama told the Chicago Tribune that he had backed Tillman because she was an early supporter of his 2004 U.S. Senate campaign.
Many speculate Obama only bothered to weigh in on a paltry city council election during his presidential campaign as a gesture to Chicago's powerful Mayor Richard M. Daley, a Tillman supporter. Even so, Obama should have remained neutral, says Timuel Black, a historian and City Colleges of Chicago professor emeritus who lived in Obama's state Senate district.
"That was not a wise decision," Black says. "It was poor judgment on his part. He was operating like a politician trying to win the next step up."
Obama has spent his entire political career trying to win the next step up. Every three years, he has aspired to a more powerful political position.
He was just 35 when in 1996 he won his first bid for political office. Even many of his staunchest supporters, such as Black, still resent the strong-arm tactics Obama employed to win his seat in the Illinois Legislature.
Obama hired fellow Harvard Law alum and election law expert Thomas Johnson to challenge the nominating petitions of four other candidates, including the popular incumbent, Alice Palmer, a liberal activist who had held the seat for several years, according to an April 2007 Chicago Tribune report.
Obama found enough flaws in the petition sheets — to appear on the ballot, candidates needed 757 signatures from registered voters living within the district — to knock off all the other Democratic contenders. He won the seat unopposed.
"A close examination of Obama's first campaign clouds the image he has cultivated throughout his political career," wrote Tribune political reporters David Jackson and Ray Long. "The man now running for president on a message of giving a voice to the voiceless first entered public office not by leveling the playing field, but by clearing it."
Three years later, in September 1999, Obama was already preparing his first national campaign. He ran for U.S. Congress against veteran incumbent Bobby Rush, a former co-founder of the Illinois chapter of the Black Panther Party.
Rush painted the largely unknown freshman lawmaker as an out-of-touch elitist, and won the 2000 primary by more than 30 percentage points.
Three years later, in January 2003, Obama announced his bid for the U.S. Senate, where he cruised to victory thanks to the self-destruction of his top opponents in both the primary and general elections.
Obama joined a crowded field of seven candidates vying to fill an open Senate seat being vacated by retiring two-term incumbent Peter Fitzgerald. For months, he polled in the middle-of-the-pack behind frontrunner and former securities trader Blair Hull, who spent $30 million of his own fortune on the primary.
But Hull's campaign imploded just weeks before the election when his divorce files were unsealed, revealing an ex-wife's charges of verbal and physical abuse.
Obama unleashed a barrage of television ads just before the election, when the other candidates had largely depleted their war chests. He won the nomination with 53 percent of the vote.
In the general election, Obama squared off against another multimillionaire: Jack Ryan, who later dropped out of the race after a judge ordered his divorce files unsealed. The documents revealed that Ryan's ex-wife, actress Jeri Ryan, a former Miss Illinois best known for her role as Seven of Nine on Star Trek: Voyager, accused him of trying to coerce her to perform sex acts in public.