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.

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

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.

But those relationships may also create the perception he is out of touch with the minority voting blocs that matter in getting elected to the mayor’s office. Far afield from the high-rise condo buildings that line Lake Michigan are blue-collar communities largely populated by blacks and Hispanic immigrants.

About 28 percent of Chicago’s residents are Hispanic, a sharp increase from 20 percent in 1989, the year Chicago Mayor Richard M. Daley started his first term. Mayor Daley is credited for successfully building ties with Hispanic voters by creating the Hispanic Democratic Organization, a powerful coalition of community leaders loyal to city hall.

Critics say Emanuel has done little to build support among blacks and Latinos. Some fault him for keeping immigration reform and civil rights issues from the White House agenda.

His challengers are predominantly all minority candidates, including James Meeks, a state senator and local Baptist minister, Chicago City Clerk Miguel del Valle, Rep. Danny Davis (D), and Rep. Luis Gutierrez (D). Many minority leaders, including several aldermen, have already made public statements saying they will not support Emanuel’s candidacy.

“These are potentially very serious disadvantages,” says Dunn.

Compounding Emanuel’s difficulties is the expected candidacy of Cook County Sheriff Tom Dart. Mr. Dart, who is white, is well-liked among black and Latino voters because of his highly publicized refusal to evict renters of foreclosed buildings and his aggressive involvement in punishing the owners of a historic black cemetery in Chicago’s south suburbs who illegally exhumed 300 bodies for profit.

Emanuel’s greatest challenge may be overcoming the perception that he is an outsider in a city that relishes local pedigree. He was born in Wilmette, a wealthy North Shore suburb, and most of his political life has been spent in Washington. Many here recall a dramatic moment during his 2002 run for Congress when he was derided as a “millionaire carpetbagger” by Edward Moskal, the late president of the Polish American Congress, a political action committee that endorsed his opponent.

He also suffered from a revelation earlier this week that he is having difficulty actually returning to Chicago as a resident, when the Chicago Sun-Times reported the leaseholder of Emanuel’s home in the Ravenswood neighborhood refused his request to move out early. Local election laws stipulate that any mayoral candidate must prove they are a city resident for at least one year before election day. The issue is expected to become one opponents will use against him during the campaign.