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In October, the mayor and Wasson unveiled a pilot program in 70 Chicago public schools to encourage parental involvement by offering parents $25 on new Walgreen Balance Rewards cards if they picked up their children's report cards.

Emanuel said Wasson volunteered after the mayor explained the problem while the two men attended a charity dinner.

"And Greg says, 'We're in, we'll do it,'" Emanuel told reporters.

In December, Emanuel stood in a new Walgreens store before a phalanx of news cameras while urging city residents to get a flu shot. Later that month it was disclosed that Walgreen had received the no-bid contract to do wellness screenings for thousands of city employees.

City officials said that while no bids were sought, they also talked to representatives from the rival CVS pharmacy chain before deciding on Walgreen.

"After a review of both Walgreens and CVS, including the greater access to 24-hour pharmacies that Walgreens offers, the city chose us as a provider for these health care services," Walgreen spokesman Michael Polzin said.

While the value of the city contract will max out at $700,000, the partnerships are likely to boost foot traffic in Walgreens stores. Even more, Emanuel provides the type of celebrity endorsement that businesses value.

"So to have a mayor attached to your brand in that way -- and you haven't paid for it -- gets you a good deal of results," Northwestern's Calder said.

Some of the most successful partnerships are forged through World Business Chicago, the nonprofit organization Emanuel significantly expanded in size and influence. The organization, which meets privately with Emanuel to strategize on economic development, has become a power center for the area's business leaders. Wasson and many other top CEOs are on the board of directors.

World Business Chicago was central to one of Emanuel's first big efforts to get the business community to pony up for the city -- a fundraising call for the 2012 NATO summit.

Much like Daley's call for private aid when he was trying to lure the 2016 Olympics here, Emanuel sold the NATO summit as an effort to put Chicago on the national stage. Major companies donated $33 million for the summit.

The requests didn't stop there.

Some have been traditional capital projects, such as Exelon, CNA and Boeing donating millions of dollars for the Bloomingdale Trail project and other companies pledging support for the $55 million Maggie Daley Park project. Others have been more obscure, such as Wal-Mart paying $25,000 to fund door-to-door visits to make sure children show up for the first day of school.

Business and political insiders say Emanuel does much of the asking himself, reminiscent of his days as a legendary political fundraiser for Daley and national politicians, including President Barack Obama. He personally and relentlessly works his cellphone contact list, one day quietly pressing a CEO for help and the next calling just to schmooze.

His friendship with William Brodsky, chairman and CEO of the Chicago Board Options Exchange, serves as one example of how the mayor's path through the halls of politics and business have led to strong ties. CBOE was a NATO sponsor and Brodsky serves on the World Business Chicago board.

"I've had a long, very positive relationship with the mayor," said Brodsky, who met Emanuel years ago while they were raising campaign money for Daley and continued the relationship while Emanuel was a key White House staffer. In his investment banker period, Emanuel worked with the CBOE, Brodsky recalled.

The mayor helped CBOE and other city exchanges win favorable state tax code adjustments in Springfield in 2011. But Brodsky said there "never ever has been any quid pro quo."

"It's not necessary because we all have the same motivation -- how to make the city more competitive," he said.

Privately, several city business leaders say that while they support Emanuel's leadership, they'd like to see a more cohesive plan for tapping the private sector -- and for measuring results. Some pointed to the mayor's most recent and largest ask -- $50 million over five years to fund as-yet unspecified anti-violence programs.

"There's no plan, there's no measuring outcomes," said a prominent business executive who spoke on condition of anonymity.

With some business leaders still miffed that $10 million in unused NATO donations were allocated to other projects and not returned to contributors, the executive said, "Everyone is looking at each other and saying, 'Here it comes again.'"

Still, the business community is stepping up again, in part because of faith in the initiative's leadership.

Tom Wilson, chairman, president and CEO of Northbrook-based Allstate Corp., is center stage among business leaders on the project along with Loop Capital's Reynolds.

Wilson said he had been working for about 18 months with Emanuel and Cook County President Toni Preckwinkle on a collaborative effort with the business sector to develop a coherent anti-violence strategy.

But the idea that businesses would raise $50 million for a large-scale effort wasn't raised until Feb. 20, about three weeks after the shooting death of 15-year-old Hadiya Pendleton brought Chicago's rising homicide rate into the international spotlight.

Emanuel held a news conference to showcase the effort, including Allstate's pledge of $5 million. So far the business community has pledged $18.5 million, Emanuel spokeswoman Sarah Hamilton said Monday.

Wilson sees his involvement as falling in line with a long tradition of corporate involvement in civic affairs, one that goes back to early 20th-century Chicago.

"Daley leveraged that, and Rahm does as well," he said. "I think it's a smart move by a politician, as opposed to demonizing business. It's smart for his objectives."