When I last spoke to Ashwini Chhabra in April, the always dapper Taxi and Limousine Commission deputy was explaining local rules that protect riders from the downside of e-hailing apps like Uber. So I didn't anticipate Chhabra's sudden move from regulator to corporate fixer.

But looking back at the revolving door between Uber and former Bloomberg administration officials, I should've seen it coming.

On Monday Chhabra—the TLC's former deputy commissioner for policy & planning and a former senior policy advisor to Bloomberg—announced his new role as the first head of policy development and community engagement for a multi-billion dollar company that wants to put taxis out of business.

Chhabra switched sides just days after city officials voted unanimously to extend a successful pilot program testing out apps like Uber, Hailo, and Taxi Magic in a yellow taxis. According to the New York Times, the former official is already singing CEO Travis Kalanick's anti-regulatory tune:

During his tenure as deputy commissioner for policy and planning, Mr. Chhabra said, the agency did not always progress as quickly as he would have liked on smartphone apps.

"I won't say that at New York T.L.C., we always got it right," he said. "Regulators often move slower than entrepreneurs."

On stage at last year's TechCrunch Disrupt in New York last April, Chhabra sort of telegraphed his move. During a panel with the CEOs of Hailo and Sidecar, moderator Ryan Lawler asked Chhabra why the taxi commission had chosen Uber as the first e-hailing approved for yellow cabs, when Uber had previously flouted local regulations and been shot down by the agency, which warned drivers they faced fines or suspension for using the app.

"What happened there in between them thumbing their nose at you?" asked Lawler.

"I have a four-year-old, so I've got thick skin," Chhabra responded, comparing the company to big baby billionaires. "You can't hold a grudge and operate effectively in government." Besides, he added, "You can't work for Mike Bloomberg and not be thinking about what's next and how do we leverage technology to make whatever this is better."

Funny that Chhabra should mention the mayor as a couple Bloomberg veterans were also, at one point, on Uber's payroll. Bradley Tusk, who managed Bloomberg's 2009 mayoral campaign, began assisting Uber with its considerable regulatory hurdles around the country in mid-2011. His company Tusk Strategies, a bipartisan political firm, also represented the secretive, anonymous donors behind Use Your Mandate, among other campaigns. (I've reached out to Uber to confirm that he's still helping the company and will update the post when I hear back.)

Meanwhile, Stu Loeser became a spokesperson for Uber after leaving "the longest tenure of a press secretary in City Hall for decades" in December. In a New York Times piece about Loeser's departure, Tusk himself described Loeser and Bloomberg as "almost like an old married couple at this point." Loeser and his firm still consult for Uber, but are not on staff.

When I poked into whether this gave Uber a political advantage last April, Loeser told Valleywag:

"Thanks for the vote of confidence, but Uber handled the approval process with the TLC themselves. And because Uber streamlined their e-hail process so significantly, there wasn't much for the TLC to not approve."

At the time, Allan Fromberg, a spokesperson for the TLC said having Tusk and Loeser in Uber's corner didn't give them a leg up, "aside from them being savvy professionals, not really."

It should be noted that there are City Hall alums on the opposing team as well. Randy Mastro, a former deputy mayor for the Giuliani Administration and Bill Thompson's biggest fundraiser, represented livery drivers and black car station owners in their failed lawsuit to try to stop e-hailing apps for taxis. Then there's former TLC chairman Matthew W. Daus, current president of the International Association of Transportation Regulators, a vocal critic of Uber who coined the phrase "rogue" app.

Connected lobbyists are no guarantee that decisions will go your way. Tusk was hired by Stanford University to help their bid to build an applied sciences campus on Roosevelt Island, which ultimately went to a partnership between Cornell University and Israel's Technion.

As the stakes (and valuations) rise, it seems inevitable that the tech industry will co-opt not just the media that once covered them, but the authorities that used to govern them, as well.

To contact the author of this post, please email nitasha@gawker.com.

[Image via Getty]