Chicago Mayor Rahm Emanuel has been one of the more famously partisan left-wingers in recent memory, but despite that reputation, he has been the happy recipient of millions in donations from Republicans in this political fight of his life. And desperate for support, Emanuel is turning to the city’s small GOP contingent to regain office.

Despite having the advantage of millions of dollars in his campaign war chest, Emanuel is still in a runoff election that months ago many thought he would easily avoid.

Much of the cash in that campaign war chest has been filled by donations from deep pocketed Illinois Republican moderates along with the usual who’s who of the state’s liberals. But as Josh Kraushaar reports, Emanuel has been quietly relying on a host of Republicans for support in this now contentious re-election campaign.

Illinois’ Republican Senator Mark Kirk, the state’s new Republican Governor Bruce Rauner, and super rich moderate Republicans have all rallied to Rahm’s side in this election.

Emanuel won the largest number of votes in last month’s city-wide election but did not reach the 50 percent plus he needed to win re-election outright. Jesus “Chuy” Garcia, Rahm’s closest opponent, received only 28 percent in the five-way election, but it was enough to keep Rahm under 50 percent. Hence, the mayor was forced into the first runoff election in Windy City history.

Since then, Emanuel has desperately tried several new tactics to win back a skeptical electorate. He even tried to dull his sharp edges in a recent campaign commercial trying to appear as Mr. Nice Guy instead of the tough-talking pol everyone knows he is.

With the election as close as it is, Rahm has been playing a double edged game by quietly promising business and moderate Republicans that he’ll keep their interests in mind while trying not to upset the left-wing power base in the Windy City.

Emanuel hopes to convince the city’s GOP voters that he is the more “conservative” candidate compared to the ultra liberal Chuy Garcia.

“The difficult task for Emanuel is to win their support while not alienating the more-progressive elements of the electorate,” Kraushaar reported on Wednesday. “So the mayor is raising big money from wealthy conservative donors while sending a subtle message in his campaign ads that is designed to scare the more-affluent constituencies in the city–without trumpeting support from the Right. He has welcomed Rauner’s quiet outreach for his campaign while also blasting the governor for his proposed budget cuts.”

But things are not going as well as Rahm had imagined they would only a few months ago.

“The people on Rahm’s campaign are really worried,” an Emanuel insider said. “I don’t feel like they think they have a good handle on how they take him down and win this thing. Rahm’s mystique was the inevitability of success, and once you strip that away, more voters think this thing isn’t a lock.”

For his part, Garcia doesn’t have much campaign cash but has racked up a series of important endorsements. He was the early recipient of support from the city’s teachers, but over the last few weeks he also got the nod from Jesse Jackson, and the city’s black ministers, as well as the powerful Service Employees International Union.

Garcia has come sometimes within double digits of Emanuel in this election that has become surprisingly competitive.

Follow Warner Todd Huston on Twitter @warnerthuston or email the author at igcolonel@hotmail.com