10.02.10 6:59 PM ET
Rahm's Toughest Hurdle
Rahm Emanuel might seem an untouchable in the race for mayor of Chicago. He's got cash to burn, a virtual letter of recommendation from President Obama, and a reputation as an ass-kicker in a city that celebrates tough guys.
Before he thinks about getting cozy in Mayor Daley's chair, however, he'll have to contend with the sheriff in town, Tom Dart.
As the Cook County Sheriff, Dart, 48, has cultivated uncommon political street cred among Chicago's typically fractious blocs: liberal reformers, old Democratic Party machine loyalists, latte sippers along the lakefront, barber-shop customers on the South Side, and union hard-hats in the labor halls.
"Tommy Dart is one hot political property," said Don Rose, a longtime political strategist. "He is clearly the main competition for Rahm Emanuel."
Dart, who has yet to announce his candidacy—taking the same coy stance as Emanuel and 15 or so other possible contenders—has garnered glowing press in the last few years.
He reformed policies on foreclosure evictions, busted a prostitution ring on Craig'slist, cracked down on dog-fighting, and won praise among black clergymen for allowing them easier access to inmates in the county jail.
"It's very rare for a white politician," said Pastor Larry Barnes of the Temple of the Living Word Church, "to have earned the kind of trust that Dart has earned in the black community."
Dart has a local Democratic pedigree—his father, Bill Dart, was a lawyer for Mayor Richard J. Daley—and commands a strong following among the precinct hustlers needed for a ground campaign. He is a former state legislator who represented a district that was overwhelmingly African-American.
He is handsome and charming. He is also an Irish Catholic.
While it is "no longer a prerequisite" to be Irish Catholic to win City Hall in Chicago, as Rose put it, "it certainly doesn't hurt."
Emanuel would be the city's first Jewish mayor. William Singer, a former Chicago alderman, can vividly recall anti-Semitic taunts during his bid for mayor in 1975.
"The city has become more mature," said Singer, an Emanuel supporter. "I don't think I'm being Pollyanna-ish."
Emanuel will also face some skepticism among voters about his ties to Chicago. A child of the affluent suburb of Wilmette, Emanuel has spent much of his career in Washington. It does not help that he once misspelled he name of Cub former star Ryne Sandberg and gave the wrong address for Wrigley Field.
"He's going to have to overcome the idea that he's not really a Chicagoan," said Dick Simpson, a former Chicago alderman and now a professor at the University of Illinois at Chicago. "The carpetbagger thing has a ring of truth."
While Emanuel will be helped by his ties to Obama, who remains largely a hometown hero in Chicago, most analysts insist the coattails won't make the ultimate difference.
A group led by African Americans on the city council has been meeting in attempts to unite around a consensus black candidate. The February election will narrow the field to two, unless a candidate wins more than 50 percent of the vote. In a crowded field, more than one black candidate could mean that no African American makes it to the final runoff, which would be held in April.
Congressman Danny K. Davis, one of the potential black candidates, said some African Americans resent the notion that Emanuel believes he is headed back to Chicago "for a coronation."
Davis, 69, who served on the City Council between 1970 and 1990, suggested that "the Rahm mystique will fade" when he begins trudging for votes among ordinary Chicagoans at El trains and bus stops.
While Davis finds plenty of shortcomings he perceives in Emanuel, he has a hard time finding anything negative to say about Dart. "I had lunch with Tom at the jail two weeks ago," he said. "He's a good man."
“It’s very rare for a white politician to have earned the kind of trust that Dart has earned in the black community,” said Pastor Larry Barnes.
On Friday, while Emanuel was being given a fawning sendoff by Obama and other officials at the White House, Davis was having breakfast in a South Side union hall with trades workers.
Tom Dart was having breakfast there, too. Some of his loyalists in the Southwest Side precincts are making a prediction: If Emanuel tries to play hardball with Dart, the sheriff will eat his lunch.
Emanuel is a national figure, and Dart, for now, is scarcely known beyond the borders of Cook County.
Once upon a time, back in the early '50s, the same could have been said of a rising young Chicago politician named Daley.
Dirk Johnson is former Chicago bureau chief for Newsweek and The New York Times.