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Their daydream was that Michelle Obama would come home to lead the city, but in the realm of possibility they weren't sure who else could seriously challenge Rahm, for one simple reason.
"You'd need lots and lots of money," as one of the west-siders put it.
It's not an abstract theory. Mayor Emanuel has alienated a few large swaths of Chicago. His poll numbers have tanked. Other elected officials have begun to question him—openly, no less—and some leading ministers have yearned aloud for a mayor who shows some "heart for the people." But Emanuel continues to make the kinds of friends who keep on giving.
Even more than Mayor Daley before him, Mayor Emanuel has the ability to bury opponents under piles of checks from the wealthy and well connected. Potential rivals across the nation took note when he raised $14 million in about four and a half months leading up to his 2011 mayoral election romp. If anything's changed since then, it's only that he's added a second prolific campaign committee and can host meetings with friends, donors, and favor seekers right in City Hall.
Perhaps there's no better example of the advantage of incumbency than how players involved in the city's despised parking meter privatization deal have ended up enhancing Emanuel's campaign funds.
Emanuel has repeatedly vowed to fight the deal, going so far as to contest bills submitted by the firm that controls the street parking system. More quietly, though, he deployed city attorneys to help Chicago Parking Meters LLC fend off a challenge to the deal in court. And they were successful. Last November a judge dismissed the challenge, ruling that the deal may be lousy but can't be considered illegal as long as the city claimed to be benefiting from it.
Two months later, Winston & Strawn, the high-powered firm that represents Chicago Parking Meters, held a reception for Emanuel that yielded at least $22,500 for his campaign coffers, according to state records.
That's a good chunk of change in the neighborhoods where the mayor is planning to close schools. But it barely ranks the firm in the top echelon of Emanuel donors. Since he was sworn in, 15 other firms or households have given more than Winston & Strawn.
Topping the list is another prominent law firm, Kirkland & Ellis, whose partners contributed nearly $109,000 to the mayor, much of it at a December fund-raiser. The city's top lawyer, corporation counsel Steve Patton, was previously a partner at Kirkland.
Nearly as generous were the leaders of Chopper Trading, a financial trading firm whose CEO, Rajiv Fernando, has hosted fund-raisers for Emanuel and President Barack Obama. Chopper employees gave about $108,000.
In fact, lawyers, financial investors, and venture capitalists dominated the list of mayor's biggest donors, just as he's made time in his schedule to meet with them privately. Among the notable contributors:
* Grosvenor Capital Management, a hedge fund whose CEO, Michael Sacks, is an unpaid Emanuel adviser and the appointed head of World Business Chicago, the city's economic development agency ($60,000).
* Lawyers at Jenner & Block, which has done millions of dollars of legal work for the city, much of it related to O'Hare expansion ($30,000).
* Partners at Schiff Hardin LLP, which has been paid millions of dollars to defend police-related lawsuits and work on city bond sales ($25,000).
* A couple of pipe fitters' unions also sent checks. The United Association and Illinois Pipe Trades each donated $50,000 after Emanuel hiked fees to pay for new water and sewer lines.
* Smaller donations were also sent in from employees of the Chicago Cubs, which has been angling for a deal with the city to help fund Wrigley Field renovations; Greenberg Traurig, whose lawyers helped draw up the city's billboard privatization deal; and Katten Muchin, the firm that put together the parking meter deal and now employs former Mayor Daley.
Not surprisingly, there were no checks from teachers' unions.
Add it all up and the mayor is sitting on about $2 million in campaign money—and this is the fund-raising off-season for Emanuel. He can, and will, turn on the spigot whenever he's ready.
A political adviser for Emanuel didn't get back to me, thus missing the chance to explain how supporters believe in the mayor's approach to fixing Chicago's economy, streets, and schools.
Anyone mulling a challenge in 2015 needs to raise at least $5 million and get the endorsements of some corporate CEOs, says one veteran Democratic strategist. It's about more than having cash to spend. "The media still needs to keep score, and one of the places they get stats to keep score is fund-raising," the strategist says. "If tomorrow someone announced they'd raised a million dollars from individual donors, that would get people's attention."