Chicago mayor: If not Rahm Emanuel, then who?

The announcement by Chicago Mayor Richard M. Daley Tuesday that he will not seek a seventh term is presenting the city a situation it has not experienced in over 20 years: a free-for-all election Feb. 22 with as many as a dozen candidates expected to seek the top seat at city hall.

Mayor Daley has reigned relatively without challenge since he took office in 1989, earning him the nicknames “Mayor For Life” and “King Richard.” But with his public approval ratings at an all-time low, a parking meter deal that continues to earn public scorn, his administration pocked with many high-profile corruption scandals, and the city saddled with a $654.7 million budget shortfall, Daley is offering up the keys to a kingdom that, in its current state, will present any candidate a significant challenge to reform.

The best-known contender is White House Chief of Staff Rahm Emanuel who, on a talk show earlier this year, let slip his interest in running for the Chicago mayor’s office should Daley choose not to continue. While he certainly has the war chest to run – $1 million according to the Chicago Sun-Times – his viability as a candidate remains in doubt. Mr. Emanuel may be popular inside the Beltway, but in Chicago he is seen as brash and, having grown up in the city’s posh North Shore suburbs, an opportunist.

Larry Bennett, who teaches political science at DePaul University in Chicago, says an Emanuel win “would be a long shot” and, as a candidate, he “could be easily attacked” as someone who was not a consensus builder and would not necessarily understand the nuances of Chicago’s tribal political culture.

To Bernard Stone, a longtime Chicago alderman who represents the city’s 50th Ward on the far North Side, Emanuel “doesn’t have the experience and the know-how.” “Rahm is a strong arm … and I am not looking for a strong-arm mayor,” he told the Chicago Sun-Times.

US Rep. Jesse Jackson Jr. (D) is another national figure that publicly made it clear he intended to run for the mayor’s office, but his chances were diminished this summer when it became public in the federal trial of impeached Illinois Governor Rod Blagojevich that he met with Mr. Blagojevich’s representatives to discuss being awarded the US Senate seat previously held by President Obama.

That revelation did not prevent Mr. Jackson’s wife, the Chicago Alderman Sandi Jackson, from telling NBC Wednesday that she and her husband were both “considering” a run for Daley’s former seat. “My husband and I will sit down and decide if either of us will run,” she said.

While the field of contenders is long, here are several that political watchers here say top of the list:

Tom Dart. The Cook County Sheriff and former state senator was named one of Time Magazine’s “100 Most Influential People” last year for his bold stances, including his refusal to carry out evictions on foreclosed homeowners and the aggressive tactics he’s taken against gangs. He also has Daley’s pedigree: an Irish-American from the South Side whose father was a confidant of Mayor Richard J. Daley.

Edward Burke. One of the longest-serving aldermen in city council, Mr. Burke, who represents the 14th Ward, is the ultimate political insider and a fervent Daley loyalist. He too has a massive war chest and a statesman-like demeanor, but the challenge of his candidacy will be winning the black vote due to what Bennett calls “baggage from the Harold Washington years” when Burke, as leader of the city council, became the late mayor’s most visible public nemesis.

David Orr. The long-time Cook County Clerk is considered one of the city’s most respected, efficient, and even-keeled political figures in a city. Mr. Orr is particularly well liked by the progressives and is widely respected for his views that have run against the city hall grain, including his criticism of Daley’s controversial deal to privatize the city’s parking meters.

Patrick Fitzgerald. This notoriously tight-lipped US Attorney is praised in this city for successful convictions against many high-profile political figures and operators including former Illinois Governor George Ryan. He is also leading the continued federal case against Blagojevich. The Daley administration has not escaped Mr. Fitzgerald’s crosshairs – he successfully won a conviction against James Laski in the notorious Hired Truck scandal of 2006, which, as Chicago City Clerk, made Mr. Laski the highest-ranking Chicago official next to Daley to be sent to prison.

Luis Gutierrez. US Rep Gutierrez is not without scandal – he was criticized for using his influence to get his daughter a job with the Blagojevich administration and for lobbying Daley on the behalf of a real estate developer and campaign contributor. But Mr. Gutierrez always has been in the running for mayor in case Daley ever stepped down. He released a statement Tuesday that said he is talking with his family and supporters about “future plans.”

Besides the well-known, somewhat-known, and not-so-well-known political figures vying for the mayoral seat, there remains a strong possibility that a left field candidate from Chicago’s business community may step into the spotlight and announce their candidacy. Bennett says he expects to see mobilization among city business leaders to support a candidate who may benefit from not being perceived as representing the city’s vanguard political culture, which many see as corrupt and inefficient.

"Chicago has not produced a serious candidate for mayor who has been outside the broad party loop in a very long time,” says Bennett. “This is the moment for it.”

Mayoral candidates must file their petitions between Nov. 15 and 22 to get their name on the ballot.