Many free-market thinkers have cheered Uber‘s ability to shake up entrenched taxi interests through superior use of technology in the absence of government guarantees.

Those same thinkers are less likely to enjoy Karen Weise’s feature story in the latest issue of Bloomberg Businessweek. It focuses on former Obama operative David Plouffe’s efforts to help Uber cozy up with local politicians in targeted markets.

Charlie Hales, the mayor of Portland, Ore., was running a zoning hearing last December when he missed a call on his cell from David Plouffe, the campaign mastermind behind Barack Obama’s ascent. Although Hales had never met him, Plouffe left a voice mail that had an air of charming familiarity, reminiscing about the 2008 rally when 75,000 Obama supporters thronged Portland’s waterfront. “Sure love your city,” Plouffe gushed. “I’m now working for Uber and would love to talk.”

Hales, like many mayors in America, could probably guess why Plouffe was trying to reach him. Uber’s made a name for itself by barging into cities and forcing politicians to respond. It started in 2010, providing swanky rides at the tap of an app in San Francisco. “I pushed a button, and a car showed up, and now I’m a pimp,” Chief Executive Officer Travis Kalanick said four years ago. The company has since expanded to take on lower-cost taxi service in more than 300 cities across six continents, ballooning to a $40 billion valuation. At the time of Plouffe’s call, Uber already operated in several Portland suburbs, and over the previous few months Hales’s staff had asked the company to please hold off on a Portland launch until the city could update taxi regulations. Plouffe may be a big name, but Hales didn’t immediately call him back.

The next day, City Hall heard from a local reporter that Uber cars would hit the streets that very evening. The company’s unauthorized kickoff put Hales in a bit of an artisanal pickle. Portland had just become the first city to explicitly allow short-term rentals through Airbnb and other sites, and welcoming Uber could help build the city’s sharing-economy brand, a logical extension of its communitarian roots. On the other hand, aggression is so not the Portland way.