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The Messy Politics of Illinois and Uber

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    As Uber plows into the taxi industry in Illinois with its eye on dominating Chicago, the fast-growing ride-share start-up has recruited a powerful ally to handle the messy political side of things.

    The news that President Barack Obama's former adviser and campaign strategist David Plouffe has joined the company as senior VP of policy and strategy delivers a strong message to its enemies: Uber means business. How dare you disrupt our disruption? You're going down.

    Here in the Land of Lincoln, Plouffe's hiring adds another layer of awkward personal politics to the Great Uber Debate. It's an increasingly tangled web: Plouffe worked in the White House alongside Rahm Emanuel when the Chicago mayor was Chief of Staff. Emanuel, trying to strike a balance between Uber-friendly and cabbie-considerate, recently passed a bill that restricts Uber drivers from picking up passengers at O'Hare, Midway and McCormick Place. (Ay, but there's a loophole: City transportation brass reserve power to open the commuter centers to ride-share disrupters, thereby cutting into the traditional cab territory.)

    Further complicating matters, Emanuel's brother, Hollywood super-agent Ari Emanuel, has invested in Uber. The Democratic mayor, up for re-election in February, is a long-time friend of Bruce Rauner, an ex-venture capitalist running a successful grassroots campaign for Illinois governor on the Republican ticket. Despite their history -- the two are vacation buddies -- Emanuel is toeing the party line to support incumbent Gov. Pat Quinn in what's shaping up to be a close race on Nov. 4.

    So is Obama. And Quinn, threatened by Rauner's momentum, has tapped the president's election team to help him hold onto his Democratic base in Chicago -- a crucial, make-or-break voting bloc for the Machine.

    "Mr. Quinn is hiring lots of Obama campaign vets and stretching to motivate Chicago voters, especially African-Americans. That's almost certainly why you'll see Mr. Obama here sometime in the fall campaigning for Mr. Quinn," wrote Crain's Chicago Business' Greg Hinz in his Monday column.

    As for Rauner, he's pulling a Rand Paul and making a play for the youthful, pro-innovation, libertarian-leaning, testosterone-heavy techie vote. The Winnetka businessman declared his love for Uber in late July, calling for Quinn to veto the General Assembly's ride-share regulation bill which would mandate commercial insurance and background checks for drivers -- restrictions that Uber desperately wants to prevent.

    "Ride-share drivers should have insurance and background checks. But Pat Quinn shouldn’t sign this bill – it sends another signal that Illinois is closed to innovation," said Rauner, talking out of both sides of his mouth in a wishy-washy statement. 

    Following the Plouffe bombshell, Rauner issued another messsage of Uber-solidarity urging Quinn to squash the legislation without offering solutions for how to improve it.

    "David Plouffe’s first order of business should be to encourage Governor Pat Quinn to veto the anti-ride sharing bill pending right here in President Obama’s home state," he said. "Ride-sharing companies like Uber are exactly the type of innovative companies Illinois should be welcoming and recruiting - I know it and the President’s top people know it. Pat Quinn should know it too."

    Unlike Quinn and Emanuel, Rauner's in a position where he can publicly cozy up to Uber -- and its tech bro fans -- without worrying about backlash from taxi interests and supporters.

    If he prevails in November, Gov. Rauner will have to tone down his rhetoric -- at least in public. But he'll have plenty of allies to help Uber on its path to world domination.