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Rahm Emanuel: Why Chicago mayor bid may be his toughest race yet

Rahm Emanuel was sent off from his post as White House chief of staff by President Obama on Friday. Political analysts say he won't have it easy trying to win the race for Chicago mayor.

By Staff writer / October 1, 2010

President Obama and outgoing White House chief of staff Rahm Emanuel embrace at Emanuel's send-off on Friday.

Larry Downing/Reuters

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Chicago

Rahm Emanuel’s transition from the White House chief of staff to a Chicago mayoral candidate will not be an easy one.

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Despite a national profile and an impressive $1.2 million campaign fund that together will likely boost him to the front of the race, Mr. Emanuel faces several obstacles that political insiders here say will make his campaign the toughest yet of his political career.

The challenges are directly connected to Chicago’s deeply entrenched political culture, which is sustained by lifelong alliances. It rewards political insiders who have an institutional relationship with its neighborhoods and have built tight coalitions with its minority communities.

“It’s not as easy as waltzing back to Chicago to take the ring and think no one is going to care … that’s not quite the way it works here,” says Dick Simpson, a political science professor at the University of Illinois at Chicago and a former alderman.

Emanuel’s greatest strength is as a fundraiser, first for campaigns by national Democratic Party stars ranging from Bill Clinton to Barack Obama, and second for his own successful run to represent Illinois’ Fifth District in Congress. Yet Chicago political experts say his reputation for aggressively strong-arming donors to write big checks may have left many here feeling bruised.

“You make a lot of friends but you make a lot of enemies too,” says Ann Lousin, who teaches law at the John Marshal Law School in Chicago. “He’ll be a terrific fundraiser, but I don’t know many people who feel close to him.”

Emanuel’s strongest support is likely to come from lakeside voters, who are predominantly white and represent the wealthiest residents in Chicago, says Charles Dunn, a political analyst and former professor at the University of Illinois in Urbana. “There is a significant base there … and it’s a big-moneyed base,” he says.

Mr. Dunn says the city’s business community will also favor Emanuel’s run because of his history as a Washington power broker. Because “his pockets are overflowing with IOUs,” Emanuel will be able to call in past favors, an advantage, Dunn says, that will not exist for any of his competition.

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