From 1984 to 2006, Democrat Dorothy Tillman was an alderman (City Council member) in Chicago’s largely black Third Ward. Well known for her revealed record of municipal corruption, her uncompromising views on race, and her professed anti-Americanism, she is a longtime friend of Barack Obama. During her time in elected politics, Tillman became the leading -- and arguably most acerbic -- proponent of reparations for slavery. Claiming that America remains “one of the cruelest nations in the world when it comes to black folks,” Tillman continues to declare that the U.S. “owes blacks a debt.” In 2004 Tillman was among the politicians whose backing of Obama’s U.S. Senate run helped the latter win the vote in Chicago’s predominantly black wards.
In 2005 Tillman was an honored guest at a lecture by Louis Farrakhan, whom she praised as a patron of the community.
In 2006 a Chicago-area newspaper, Lakefront Outlook, launched an investigation into Tillman’s financial books and discovered 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 office, was marred by tax violations. The investigators further found that Tillman was engaging in blatant nepotism, hiring family members to staff the financially troubled institution. As a result of these revelations, Tillman lost her 2006 re-election bid for the City Council -- notwithstanding the support she received from her most prominent endorser, Barack Obama.
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