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   shadowy conservative cabal were so effective that the Times later   
   declared Lehane to be the modern-day “master of the political dark   
   arts.”   
      
   After serving in the White House, Lehane joined Al Gore’s Presidential   
   campaign, as press secretary, and after Gore’s defeat he set up shop in   
   San Francisco. Despite the size and the electoral significance of   
   California, many campaign operatives viewed the state as a political   
   backwater, because it was so far away from Washington. But Lehane, who   
   had worked on the Telecommunications Act of 1996, was convinced that   
   Silicon Valley was the future, and he quickly built a business   
   providing his dark arts to wealthy Californians. When trial lawyers   
   wanted to increase the state’s caps on medical-malpractice jury awards,   
   they brought in Lehane, who helped send voters flyers that looked like   
   cadaver toe tags, and produced ads implying that doctors might be   
   performing surgery while drunk. A few years later, when a prominent   
   environmentalist hired Lehane to campaign against the Keystone XL   
   Pipeline, he sent activists into press conferences carrying vials of   
   sludge from an oil spill; the sludge was so noxious that reporters fled   
   the room. Then he hired one of the Navy SEALs who had helped kill Osama   
   bin Laden to talk to journalists and explain that if the pipeline were   
   approved a terrorist attack could flood Nebraska with one of the   
   largest oil spills in American history. Lehane explained to a reporter   
   his theory of civil discourse: “Everyone has a game plan until you   
   punch them in the mouth. So let’s punch them in the mouth.”   
      
   Video From The New Yorker   
      
      
      
      
   But Lehane’s efforts generally failed to impress the tech industry. For   
   decades, Silicon Valley firms had considered themselves mostly detached   
   from electoral politics. As one senior tech executive explained to me,   
   until about the mid-twenty-tens, “if you were a V.C. or C.E.O. you   
   might hire lobbyists to talk to politicians, or gossip with you, but,   
   beyond that, most of the Valley thought politics was stupid.” Within a   
   decade of Lehane’s move West, however, a new kind of tech company was   
   emerging: so-called sharing-economy firms such as Uber, Airbnb, and   
   TaskRabbit. These companies were “disrupting” long-established sectors,   
   including transportation, hospitality, and contract labor. Politicians   
   had long considered it their prerogative to regulate these sectors,   
   and, as some of the startups’ valuations grew into the billions,   
   politicians began making demands on them as well. They felt affronted   
   by companies like Uber that were refusing to abide by even modest   
   regulations. Other companies tried a more conciliatory approach, but   
   quickly found themselves mired in local political infighting and   
   municipal bureaucracies. In any case, “not understanding politics   
   became an existential risk,” another senior tech executive said. “There   
   was a general realization that we had to get involved in politics,   
   whether we wanted to or not.”   
      
   In 2015, San Francisco itself became the site of a major regulation   
   battle, in the form of Proposition F, a ballot initiative to limit   
   short-term housing rentals, which both sides acknowledged was an attack   
   on Airbnb. The proposal had emerged from built-up frustrations: some   
   San Franciscans complained that many buildings had essentially become   
   unlicensed hotels, hosting hard-partying tourists who never turned off   
   the music, didn’t clean up their trash, and—most worrying for city   
   leaders—hadn’t paid the taxes that the city would have collected had   
   they stayed at a Marriott. Other residents argued that Airbnb’s   
   presence was making it harder to find affordable housing, because it   
   was more profitable to rent to short-term visitors than to long-term   
   tenants. Proposition F would essentially make it impossible for Airbnb   
   to work with many homeowners for more than a few weeks a year. Early   
   polling indicated that the initiative was popular. Numerous other   
   cities had been considering similar legislation, and were eagerly   
   watching to see if lawmakers in San Francisco—where Airbnb was   
   headquartered—could teach them how to rein in the Internet giant, then   
   worth some twenty-five billion dollars.   
      
   Airbnb’s executives, panicked, called Lehane and asked him to come to   
   their headquarters; he showed up within minutes of their call, in the   
   sweatpants and baseball jersey that he’d been wearing at his son’s   
   Little League game. Lehane has the lean build of someone accustomed to   
   athletic self-torture—he runs daily, often fifteen miles at a stretch,   
   typically while sending oddly punctuated e-mails and leaving stream-of-   
   consciousness voice mails—and he has a boyish crooked front tooth that   
   offsets the effect of his receding hairline. To Airbnb’s leaders, he   
   didn’t look like much of a political guru. But, once Lehane caught his   
   breath, he launched into a commanding speech. You’re looking at this   
   situation all wrong, he said. Proposition F wasn’t a crisis—it was an   
   opportunity to change San Francisco’s political landscape, to upend a   
   narrative. The key, he told executives, was to build a campaign against   
   Proposition F as sophisticated as Barack Obama’s recent Presidential   
   run, and to deploy insane amounts of money as a warning to politicians   
   that an “Airbnb voter” existed—and ought not be crossed. He proposed a   
   three-pronged strategy, and explained to executives that what   
   politicians care about most is reëlection. If the company could show   
   that being anti-Airbnb would make it harder for them to stay in office,   
   they would fall in line. Lehane was soon named Airbnb’s head of global   
   policy and public affairs.   
      
   His first step in this role was to mobilize Airbnb’s natural advocates:   
   the homeowners who were profiting by renting out their properties, and   
   the visitors who had avoided pricey hotel rooms by using the service.   
   By the end of 2015, more than a hundred and thirty thousand people had   
   rented or hosted rooms in San Francisco. Lehane recruited several   
   former Obama-campaign staffers to lead teams who made tens of thousands   
   of phone calls to Airbnb hosts and renters, warning them about   
   Proposition F. The team members also urged hosts to attend town-hall   
   meetings, talk to neighbors, and call local officials. During this   
   period, the company—accidentally, it says—sent an e-mail to everyone   
   who had ever stayed in a California Airbnb, urging them to contact the   
   California legislature. The legislature was inundated with messages   
   from around the world. The Senate president pro tem called Lehane to   
   let him know that the message had been received, and to beg him to stop   
   the onslaught. “I kind of wish we had done it on purpose,” someone   
   close to that campaign told me.   
      
   The second part of Lehane’s strategy was to use large amounts of money   
   to pressure San Francisco politicians. The company brought on hundreds   
   of canvassers to knock on the doors of two hundred and eighty-five   
   thousand people—roughly a third of the city’s population—and urge them   
   to contact their local elected officials and say that opposing Airbnb   
   was the equivalent of attacking innovation, economic independence, and   
   America’s ideals. The relentless campaign posed a clear threat to the   
   city’s Board of Supervisors: if an official supported Proposition F,   
   Airbnb might encourage someone to run against him or her. “We said the   
   quiet part out loud,” a campaign staffer said. “The goal was   
   intimidation, to let everyone know that if they fuck with us they’ll   
      
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