Obama’s Erstwhile Political Ally Dorothy Tillman is another potential Jeremiah Wright

It has been a difficult few weeks for the friends and political associates of Barack Obama.

In Detroit, Obama’s pal, former Mayor Kwame Kilpatrick has plead guilty to an assortment crimes and resigned his office to begin a prison term. Closer to home, convicted political fixer Tony Rezko is due to be sentenced shortly before election day. Reports have indicated that Rezko has begun cooperating with prosecutors in an effort to reduce his sentence. Federal investigators have also conducted a search of the home of Will County Executive Larry Walsh, who served with Obama in the Illinois Senate. Walsh was one Obama’s poker playing friends and questions have been raised about the number of federal grant dollars that Obama showered upon Will County after meeting with lobbyists employed by Walsh.

In the gone, but not forgotten category is Dorothy Tillman a/k/a “The Cat in the Hat.”

An Alabama court sentenced former Chicago alderman Dorothy Tillman to pay a $350.00 misdemeanor fine and serve a ten day jail sentence as the result of her disorderly conduct arrest in a Montgomery hospital during March of 2008. Tillman has pledged to appeal the verdict. She blamed the arrest on police brutality.

Tillman’s arrest was captured on tape by a hospital security camera. Tillman is clearly recognizable on the videotape due to her wearing one of her signature hats that have become the politician’s personal trademark. A quarrel erupted when Tillman could not immediately secure a medical report for her elderly aunt from the hospital staff. In the ensuing fight, Tillman had to be subdued by hospital security officers and removed in handcuffs.

Tillman was always an outlandish cartoon caricature of a race baiting politician. She first raised her public profile by shouting insults at interim Chicago Public Schools Superintendent Angeline Caruso during school board meetings. Community activists wanted Caruso, a white appointee of former Mayor Jane Byrne, out and a black appointee in, so Tillman used to heap verbal abuse on the beleaguered superintendent during public sessions of the board.

Tillman’s aldermanic career began as the result of her being appointed to the position by Harold Washington following his historic mayoral election in 1983. Tillman lost the 1983 election to the incumbent alderman, Tyrone Kenner, but the 3rd Ward seat became vacant a few months later when Kenner was convicted on charges of extortion and fraud. Washington tapped Tillman for the vacancy and the City Council eventually acquiesced and approved the appointment after a period of opposition. Alderman Bernard Stone was a vocal opponent of Tillman’s appointment on account of her disgraceful prior behavior in various public forums.

In the City Council, Tillman distinguished herself by wearing outlandish hats on every public occasion.

The late Mayor Harold Washington privately described Tillman as a “loser,” who was “abrasive,” “insecure,” and “too loud.” He concluded his comments by adding “She does not know how precincts work in terms of providing services.” The mayor’s comments were secretly recorded and made public by a former city worker who had considered running against Tillman in the 1987 elections.

While one may criticize Washington for promoting Tillman, in fairness, the mayor did not have many blue ribbon candidates to choose from when appointing someone to the vacancy. The 3rd Ward has been historically one of the poorest and crime infested ghettos in the city. Following Washington’s sudden death in November of 1987, Tillman continued to serve in the council and had to branch out and find new political allies. Having assumed the political position of ward committeeman, Tillman reached out to the Democratic Machine.

In 1991, during the middle of redistricting negotiations, Tillman shocked her colleagues by brandishing a gun during the heated discussions on the aldermanic map. Apparently, Tillman was able to obtain the ward boundaries and election precincts that she desired without bloodshed. Tillman made further headlines during 2000 when she created a controversy by demanding that the Palmer House remove two waiters from a banquet that she sponsored and replace the servers with two African American waiters. Tillman, who made herself a career out of decrying discrimination at every opportunity, was promptly denounced as a bigot. Even Mayor Richard M. Daley rebuked her in a public statement.

In the City Council, Tillman directed her efforts to enacting an ordinance that would require firms doing business with the city to disclose whether or not the firms had any historical ties to the promoting the institution of slavery through using slave labor directly or by selling and trading slaves. The ordinance was enacted in 2002, over one hundred and thirty-six years after slavery was abolished by the ratification of the 13th Amendment to the US Constitution. There was a method to Tillman’s madness, however, as she saw the disclosure and reporting ordinance as a prelude to securing slave reparations for descendants of former slaves.

In an unusual public television broadcast of “Chicago Tonight” that bordered upon the surreal, Tillman launched into a fiery attack of a Chicago attorney, Joseph Morris, who was chosen as the nominal conservative guest on the news program during a discussion of the subject of slave reparations. WTTW host Phil Ponce was placed in the unusual position of having to raise his voice in protest and order the alderman to halt her vitriolic attack upon the mild mannered Morris.

Barack Obama, “the Unreformer,” has had a curious relationship with Dorothy Tillman. It is not one that the presidential candidate would like to have publicized since Tillman is as a controversial and unstable in her racially charged rhetoric as Obama’s former pastor, the Reverend Jeremiah Wright.

Obama contributed $1,500.00 to the 3rd Ward Democratic Organization in March of 2004. Tillman was serving as the Democratic ward committeeman in addition to her position as alderman at the time. Obama’s contribution coincided with the primary election in which he secured the Democratic nomination with Tillman’s backing. Local opposition to Tillman was growing in the 3rd Ward and she was seen as a vulnerable incumbent in 2007.

Despite his supposed commitment to ethics and reform, Barack Obama endorsed Tillman for reelection as alderman in 2007. Obama’s endorsement disappointed labor activists and reformers who were openly critical of his choice. The endorsement did not help. Tillman, who had failed to obtain a majority in the aldermanic election, lost the run-off election to Pat Dowell. Obama attempted to justify his decision by pointing to the fact that Tillman had been one of the key supporters of his US Senate bid. In reality, Mayor Richard M. Daley and Tillman had a quiet political pact in place for several years. Daley considered the obstreperous Tillman to be a useful idiot in the council. To many observers, it seemed as if Obama had merely followed suit with the Daley camp in making his endorsement.

In the 2008 primary, Tillman did not seek another term as ward committeeman and Dowell defeated Tillman’s associate, State Representative Kenneth Dunkin (D-5th), and succeeded Tillman as the party leader in the 3rd ward. After twenty-five years in politics, Tillman appeared to be out at long last.

One question that Obama definitely does not want to be aired is whether or not he supports slave reparations payments to the same degree as does his friend Dorothy Tillman? It is an open question. Which Obama can you believe? The radical race demagogue of his two books or the nuanced and posturing candidate on the campaign trail? It is a controversial and divisive issue that Obama cannot afford to discuss.

Former President William J. Clinton suffered some embarrassment by issuing a series of controversial executive pardons while he was completing his second term. If elected in November, one wonders if Obama will begin pardoning his corrupt political associates during the Inaugural Ball. Given the scandals that Obama needs to contain for the next few weeks, some Democratic cronies are depending upon Obama to call off the prosecutorial dogs or to cut them loose from jail in January.

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Dan Kelley is a regular columnist for the Chicago Daily Observer