Action Sports with Leigh Roche

Bruce Rauner, the wealthy philanthropist who two weeks ago won an upset victory for governor of Illinois, is an enigma to many or most veterans of the political scene in President Barack Obama’s home state — but not to Chicago Mayor Rahm Emanuel.

The two men have a genuine friendship that dates back a decade and a half, to Emanuel’s brief but lucrative stint at the investment firm Wasserstein Perella in the late 1990s. There, the future White House chief of staff helped cement a half-billion dollar deal for Rauner’s company GTCR.

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In the heat of the 2014 campaign, Emanuel and Rauner kept a careful distance from each other — Rauner, after facing attacks from Republican primary opponents over his affinity for the man conservatives know as Obama’s Beltway enforcer; Emanuel, to allay suspicion on the left that he wasn’t fully invested the reelection of a Democratic incumbent with whom he publicly clashed. It was an embarrassment to both when the Chicago Tribune published a splashy August story on their friendship, featuring photos of the pair strolling together at a posh Montana resort four years earlier, Emanuel with a bottle of expensive wine in his hand.

Now, as Emanuel girds for a perilous reelection fight this winter, he and Rauner are joined by a rare bond in national politics: a relationship that could prove decisively helpful to them in governing but utterly radioactive within their respective parties. Bill Daley, the former Commerce secretary who succeeded Emanuel as Obama’s top staffer, called the ties between the mayor and Rauner a mutually beneficial link that also carries real political risk on both sides.

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“Rahm’s constituency, which he will face in three months, is a very different constituency than Bruce Rauner will ever have on his side,” Daley warned. “They have fundamentally different electorates and bases. In this state, it’s especially stark.”

But Emanuel also has much to gain from his relationship with Rauner, who holds the power to fortify or unwind much of what Emanuel accomplished in his first term. Rauner opposed a public pension overhaul Emanuel brokered in Chicago and has vowed to undo tax hikes enacted by outgoing Democratic Gov. Pat Quinn, raising the prospect of deep cuts in government spending that could fall with a hammer-blow on the mayor’s city.

Emanuel, a legendary figure in Washington, enters his reelection campaign this winter buffeted by urban crises: a wave of violent crime, an embarrassing teachers’ strike and a showdown over public pensions that enraged powerful labor unions. The mayor is taking the race seriously enough to launch an early round of television advertising this week.

He faces a pair of lower-profile, lightly funded challengers this February — Alderman Bob Fioretti and Cook County Commissioner Jesus Garcia — who have criticized Emanuel as an out-of-touch footman for the Chicago financial elite that backed Rauner so enthusiastically. (Rauner lost Chicago-based Cook County by more than 30 points, making it the only county in the state won by Quinn.) In a phone interview, Fioretti questioned the propriety of the relationship between Emanuel and Rauner — “somebody that helped give Rahm a fortune in a few months.”

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“People in the city of Chicago, wherever I go, are amazed that somebody [Emanuel] could make so much money in such a short period of time and really not do the hard work,” Fioretti said, referring to the more than $18 million Emanuel collected over a few years in finance. “It seems like Wall Street is directing his administration.”

Emanuel’s allies would object to that characterization. Speaking anonymously, backers of both Emanuel and Rauner stressed the independent, headstrong personalities both men carry into the political arena, disputing that either would be overly influenced by the other. (Said one Rauner backer: “He’s a billionaire who’s six-foot-four, who can call his buddies anytime and say, ‘Quit giving to Rahm.’”)

But Emanuel and Rauner plainly do share an overlapping set of political allies and objectives. They publicly differ on a string of crucial issues — Rauner’s opposition to the pension deal, for instance, or Emanuel’s vocal support for hiking the minimum wage — but they have a common interest in education reform and budgetary discipline. As mayor, Emanuel appointed Rauner to an advisory role leading Choose Chicago, a tourism and business promotion board from which he resigned to run for governor.

The two men draw on a heavily interlinked network of financial backers. Of the top 25 contributors to Emanuel’s Chicago Forward PAC, more than a quarter also contributed to Rauner’s campaign, according to a review of state and city finance records. One shared benefactor, billionaire Ken Griffin, was among the largest individual donors to the mayor’s committee while offering Rauner nearly $5 million and the use of Griffin’s private plane.

Perhaps most importantly, Illinois’ political odd couple also shares the unenviable challenge of navigating the powerful state Legislature, controlled by Democratic supermajorities in both chambers and lorded over by state House Speaker Mike Madigan. For a Republican governor looking to enact an agenda under those restrictive conditions, or for a Democratic mayor hoping to ensure that any spending cuts don’t fall like an ax on his city, it helps to have a friendly partner in statewide politics.

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Daley, now a member of Rauner’s transition team, suggested Emanuel could serve as “a go-between to the legislative leaders” in areas where the governor’s agenda and Chicago’s priorities overlap. Illinois Rep. Mike Quigley, the progressive lawmaker who now holds Emanuel’s old seat in Congress, called the Emanuel-Rauner relationship a possible force for good in a state where politics is played in at least three dimensions at a tim...