On his last day as President Obama's chief of staff, Rahm Emanuel accepted a going away gift from his White House colleagues -- a big fish wrapped in Chicago newspapers.
It got a good laugh.
And Emanuel, 50, who is expected to launch a campaign for Chicago mayor next week with a "listening tour" in the city's neighborhoods, didn't even have to unfurl the publications to read what has become increasingly apparent: His road to the big office in City Hall is not going to be easy.
The brusque former North Side congressman's lack of ties to the city's large minority communities has been duly noted. His Chicago residency status (he rented out his house during his stint in Washington) is being questioned by some of his many would-be opponents. And his links to Wall Street -- he earned $17 million plus as a banker between his service as an adviser in the Clinton administration and election to Congress in 2002 -- are being examined anew.
"His brand is, in many ways, attractive, but it's a fairly narrow brand," says Laura Washington, a political analyst and columnist for the Chicago Sun-Times. "It's about clout, money, connections and power."
"To win, he has got to stand for a lot more than that," Washington says, particularly in a diverse city that is facing an economic crisis and high unemployment rates, particularly in minority neighborhoods.
And especially when he is seeking to replace powerful Mayor Richard M. Daley, who has occupied the office for more than two decades, and has been seen as himself more connected to the powerful and moneyed than those in far less affluent neighborhoods, she says.
Daley is the son of the late Mayor Richard J. Daley, who ran the city from 1955 until he died in office 21 years later.
The field of candidates will emerge by the week of Nov. 15, when prospective mayoral contenders are required to submit nominating petitions containing at least 12,500 signatures. Voters, who don't register for a party but 90 percent of whom typically request Democratic ballots on Election Day, will go to the polls on Feb. 22. If no candidate pulls more than 50 percent of the vote, a run-off contest will be held April 5.
The new mayor will take office May 16.
Emanuel, who was born in Chicago but spent much of his youth in suburban Wilmette, has powerful support. Obama, who calls Chicago home, is in his corner, and that means something -- whether or not the president decides to endorse his former adviser. Emanuel also has strong money ties to Hollywood, Wall Street and Chicago's LaSalle Street business community.
"But he's still seen as something of a carpetbagger," says Dick Simpson, a former city alderman and head of the political science department at the University of Illinois, Chicago.
"He grew up in the suburbs, not the city, and has spent more time on The Hill than in Chicago," Simpson says. "And there has been a feeling of 'anybody but Rahm' among aldermen and committee members not particularly looking forward to another strong mayor."
Though Emanuel lacks foot soldiers in the city, he has name recognition and money -- some estimate that he could raise up to $5 million for his run. (And foot soldiers, notes 20th Ward Alderman Willie Cochran, "can be bought.")
Strategists say that he should run strong among predominantly Jewish "Lakefront Liberals." And though Daley won't openly endorse him, a number of the current mayor's people -- including his brother, former Commerce Secretary William Daley -- are likely to be supportive behind the scenes. As will the city's powerful business community.
In his White House remarks Friday, Emanuel teared up when remembering his parents, recalled his mother marching with Dr. Martin Luther King Jr., and made reference to the Chicago Bears.
"He's trying to show a better side," says Simpson, to counterbalance his well-earned reputation as a profane taskmaster and enforcer.
"All of that is meant to signal that he might be more friendly than thought," Simpson says.
Criticism aside, Emanuel is clearly seen as a leading candidate, if not the leader. But his competition is not inconsequential.
Simpson and others have pointed to these contenders -- all Democrats -- from the white, African-American and Latino communities (and yes, they all say, racial politics will figure strongly in a contest where coalition-building will be the key to victory. The city of 2.8 million is 42 percent white, 36.8 percent black, and 26 percent Latino):
-- White community: Cook County Sheriff Tom Dart and 2nd Ward Alderman Bob Fioretti
-- African-American community: Baptist minister James Meeks and former Illinois Sen. Carole Moseley Braun
-- Latino community: Rep. Luis Gutierrez, 1st Ward Alderman Manuel Flores and City Clerk Miguel Del Valle
First-term Alderman Fioretti, elected from a predominantly black ward, says he doesn't know what path Emanuel's campaign may take.
"I just know he's got a lot of money," Fioretti says.
And about the effect Obama's support -- if not endorsement -- might have on his former chief of staff's campaign?
"The city of Chicago loves President Obama," Fioretti says. "But will voters follow who he endorses for mayor if he goes that far? I don't think so."
After all, the alderman says, when Obama launches his 2012 campaign, does he really want to give his opponents more "Chicago politics" fodder by dipping into a mayor's race?
Many Chicago Democrats are advising the president to stay out.
"If Barack Obama endorses Rahm Emanuel, it will come back to haunt him," says Delmarie Cobb, a Chicago Democratic activist and political strategist.
Cobb says Emanuel has few connections to the black community and that leaders in the Latino community have been disappointed by the Obama administration's lack of progress on immigration reform.
"There is a very vocal black community in the city of Chicago, and there is no way that this community, which voted for Barack, is going to sit back and let the president anoint Rahm Emanuel," adds Cobb, who says she believes the administration has done little for the African-American community since Obama has been in the White House.
"If you elevate this race to a Washington contest, it becomes a referendum on the president," says Cobb, who supported Hillary Clinton's bid for the Democratic presidential nomination in 2008.
And he, and Emanuel, might not like the outcome.
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