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Rahm’s secret weapon: Fundraiser clicks with mayor

She’s the daughter of a Palestinian immigrant-turned family doctor in tiny Camden, Ark. He’s the first Jewish mayor of Chicago and the son of an Israeli-born, big-city pediatrician.

She’s a striking Southern belle with a syrupy sweet voice that could charm the socks off a hard-nosed businessman. He’s a bull in a china shop with a cartoonlike reputation for pushiness and brute-force politics. 

Fundraiser extraordinaire Anne Olaimey and her boss, Rahm Emanuel, are an odd couple. But it’s a 14-year political marriage, still going strong, that has filled Emanuel’s campaign coffers with tens of millions of dollars at every level.

As of June 30, Emanuel had $8.3 million in the bank to rebuild his tarnished image and bankroll, what could be a protracted re-election campaign that includes two rounds, instead of one.

“He’ll get half a sentence out. She’ll finish it,” said William Brodsky, chairman and CEO of the Chicago Board Options Exchange, which has given Emanuel’s campaign $35,000 since October, 2010.

“They communicate, almost without speaking,” said Grosvenor Capital Chairman Michael Sacks, a close friend and chief business adviser to the mayor.

Lori Healey watched Olaimey work her fundraising magic to the tune of $32 million in corporate donations that bankrolled the 2012 NATO Summit.

“Every CEO — whether a business leader or a mayor — needs someone you can just be yourself with. Jackie [Heard] was that person for Rich [Daley]. Anne is that person for Rahm. Their personalities work together,” said Healey, who served as executive director of the NATO Host Committee.

In a rare interview with the Chicago Sun-Times at a hotel down the street from Emanuel’s South Loop campaign office, Olaimey described her relationship with Emanuel as “like a sister-brother team.”

They talk by phone three times-a-day to “check in” about fund-raising strategy, scheduling and meeting the rigid goals they have established together.

He’s the closer when he needs to be with a lot more pleases, thank yous and cheesecakes than his take-no-prisoners reputation would lead anyone to believe.

But she decides whom to target and feels out corporate lobbyists to determine how much money is even available for political donations.

She also talks to CEOs she knows from the trade missions they went on together during her days as business liaison for the U.S. Department of Commerce in the early years of President Barack Obama’s administration.

“People know me, so I’m able to pick up the phone and call somebody. I didn’t come to Rahm as, ‘Teach me how to do this.’ I came to him already seasoned [saying], ‘Here’s what I think we should do.’ It’s a very sophisticated operation,” said Olaimey, 43, who started in her 20s as an unpaid intern at the Democratic National Committee.

“Rahm is a very demanding person. He’s had my job and he did it beyond well. But I like that it’s tough. I like being kept on my toes. . . .  I try to deliver the exact number. I don’t feed him bull – – – – . . . I’m not afraid of him if he yells at me. I don’t care. He’ll sass me. I’ll sass him back.”

Olaimey acknowledged that the unlikely partnership works, in part, because her soft-sell Southern charm is the perfect complement to Emanuel’s brashness.

“I disarm everybody. I don’t have any airs about me. I make it easy for people to come up to him,” she said.

Alyssa Mastromonaco served under then-White House chief of staff Rahm Emanuel during her days as director of scheduling and advance.

She has witnessed firsthand the unbelievable chemistry between Emanuel and Olaimey.

“They are, personality wise, sort of polar opposites. Anne is this effervescent, wonderful person from Arkansas who’s unbelievably upbeat and can take the edge off anybody. Rahm can be really tough. Somehow together, they are very yin and yang,” said Mastromonaco, one of Olaimey’s closest friends.

“She likes that she never knows what Rahm is gonna throw at her, and he likes that he can always, always count on her. Rahm has really strong ideas of what should happen. Anne takes those ideas and makes them really work.”

Mastromonaco and Olaimey are part of a high-powered network of fundraisers in Washington, D.C., that makes Olaimey all the more effective.

The sorority also includes Stephanie Cutter, the deputy campaign manager for Obama’s 2008 and 2012 campaigns, who now serves as co-host of the CNN program, “Crossfire,” and Julianna Smoot, Obama’s 2008 finance director and former deputy campaign manager who’s now the chief fundraiser for the Obama library.

Mastromonaco said Olaimey’s insights into what makes Emanuel tick helped her adjust to her new boss.

“Rahm can be a very intimidating person, but Anne really helped me to understand the magic of Rahm. He’s one of the most creative, smart and hardworking people I’ve ever worked for. Because of her great relationship with him, my relationship with [him] was all the better for it,” she said.

When former Mayor Richard M. Daley announced his decision to retire from politics in September 2010, Olaimey was one of the first people Emanuel contacted. According to Olaimey, he said, “If I do this, you’re coming with.”

They had worked together on his 2002 campaign for Congress and at the Emanuel-chaired Democratic Congressional Campaign Committee, which engineered the 2006 Democratic takeover of the U.S. House.

Together, they raised $14 million to bankroll Emanuel’s 2011 mayoral campaign, $6 million of it in the first six weeks as they raced to beat a Dec. 31 deadline before fundraising limits took effect.

Next came the NATO Summit to deliver on Emanuel’s bold and risky guarantee that the event would be privately financed.

“It’s not easy to make a donation to the NATO summit when you don’t get something for it,” Healey said.

“NATO had pretty stringent rules and regulations about how sponsors could and couldn’t get recognized and what events they could and couldn’t attend. Anne was very good at pushing as hard as we could on their behalf and making sure sponsors got access to the events they wanted.”

As mayor, Emanuel has sworn off contributions from city contractors and lobbyists, but he accepted donations from attorneys and developers whose projects must be approved by City Hall.

He also has reimbursed Chicago taxpayers for $14,000 in travel expenses tied to trips that included political fundraising.

Olaimey sloughs off suggestions that the mayor’s well-oiled fundraising machine has somehow pushed the envelope.

“Everything we’re doing and everything that we’re taking is completely, 100 percent legal,” she said.

And what about unwritten understandings of future city assistance?

“We don’t do that. Every email — before I hit ‘send,’ I go, ‘How would this look on the front page of the New York Times?’ Every phone call I’m on, I talk like I know it’s being taped by the FBI. I don’t work like that. I don’t do it,” she said.

If Emanuel wins re-election — or even if he doesn’t — Olaimey hopes to graduate from political fundraising to a nonprofit job that, perhaps, incorporates her fundraising savvy with her generosity, humor, intellect and people skills.

But then, she has been saying that for years and she’s still in the thick of it.

“I am so fortunate, so lucky and so appreciative of all the good friends I have, the jobs I have and what I’ve gotten to do and see. Who am I? We didn’t grow up knowing anybody. We’re not fancy people. My dad’s from Nazareth, Israel. He came over here not knowing anybody. Seventeen years old,” she said.

“Some people get confused and think, ‘They give me money.’ No. Fundraisers — we’re like toll booth people. Everybody’s replaceable. The cars are still gonna go through and collect the money.”

Sacks says the sorority girl from a Friday Night Lights-style town in Arkansas will not easily be replaced.

“Fundraising is a tough business. To be successful, you have to be, all at once, aggressive and strong, nice and sweet. She’s great at it. She’s as successful a political fundraiser as there is,” he said.