According to the city, the Taxi King controls 860 cabs (Freidman says he actually operates more than 1,100). That’s more than anyone else in town. Factor in the hundreds of vehicles he has in Chicago, New Orleans, and Philadelphia, and he’s almost certainly the most powerful taxi mogul in the country. Freidman makes money by leasing the cabs to drivers on a daily or weekly basis. ... To own a cab in New York, you need a medallion—a metal shield displayed on the vehicle’s hood—and there are a fixed number issued by the New York City Taxi & Limousine Commission (TLC). Until very recently, medallions were a good thing to have a lot of. In 1947, you could buy one for $2,500. In 2013, after a half-century of steady appreciation, including a near-exponential period in the 2000s, they were going for $1.32 million. ... desperate medallion sellers are trying to fob off their little tin ornaments for as little as $650,000. ... This has had a profound effect on Freidman, whose net worth appears to be in free fall. ... The day the cap was defeated, 22 of Freidman’s companies, owning 46 medallions, filed for bankruptcy. ... “Honestly, I would love the piece not to be about ‘We had breakfast at Cipriani, then we walked over to his Park Avenue apartment, then we got into his Ferrari.’ ” ... If Uber is chiefly responsible for driving down the price of taxi medallions, Freidman played a big role in driving it up in the first place. Allow him to explain his strategy: “I’d go to an auction, I’d run up the price of a medallion, then I’d run to my bankers and say, ‘Look how high the medallions priced! Let me borrow against my portfolio.’ And they let me do that.” ... According to the Citibank bankruptcy filing, Freidman’s companies owe roughly $750,000 on each Citibank medallion.

The thing to do, Kalanick argued, was to make the service a low-cost accessible luxury. "If Uber is lower-priced, then more people will want it," he explains. "And if more people want it and can afford it, then you have more cars on the road. And if you have more cars on the road, then your pickup times are lower, your reliability is better. The lower-cost product ends up being more luxurious than the high-end one." Kalanick had been resisting Camp’s overtures to become CEO, but it was this insight that got him excited: Uber could be huge. ... All that struggle and setback from his first two startups set up Kalanick almost perfectly for what was to come. "If you looked at everything he’s done, I don’t think there was another human who was more destined to build Uber," says Angelo Sotira. "You had peer-to-peer networks, aggressive dealings, large lawsuits." ... This new, subdued Travis Kalanick who claims he’d never heard of a libertarian seemed to me a significant overcorrection from the badass antigovernment crusader he has played for the past few years—and also just one sliver of his actual personality. That in itself is telling. Kalanick is not the kind of person who clings to beliefs, or even a fixed sense of himself. ... Some Silicon Valley founders pride themselves on being visionaries; Kalanick exults in an ability to read the data, revise, and adapt, likening running Uber to driving a car without a clear destination in sight. ... As of this summer, Uber has cars on the road in 15 Chinese cities with plans to be in 50 next year. The results so far have been astonishing: In just nine months, three Chinese cities (Chengdu, Guangzhou, and Hangzhou) have each already accounted for more rides than New York.

On a typical day Westlake finances 750 cars. It currently has 336,000 outstanding loans, each originating from one of the 23,000 dealerships it works with (everyone from CarMax to small mom-and-pop used car lots). ... most of Hankey’s borrowers aren’t average–they are financial underachievers with credit scores below 600. Many have bankruptcies, past repossessions or limited credit histories–things that make them unattractive to traditional lenders. That’s where Hankey steps in. While Westlake offers loans as low as 1.65%, it specializes in financing credit-challenged car buyers–at an eye-popping rate of 19%, more than double the average for used car loans. ... They typically shell out $344 per month over 49 months, or $16,860 on a $12,000 loan. That translates to an extra $3,920 in interest over the life of the loan when compared to the 3.67% rate a borrower with good credit gets when buying a new car, according to Experian. Sure, each month the company has to write off about $17 million in unpaid loans, but it still banks a profit of around $20 million. In 2014 Westlake netted $230 million on $600 million in revenues. ... He joined forces with the ride-share leviathan in September 2014 as its only outside financing partner. Spanish bank Santander had been working with Uber, offering a lease-to-own program, but that relationship ended earlier this year. Would-be Uber drivers who are looking to purchase a car can get pre-qualified online in a matter of minutes. ... so far a greater portion of its Uber drivers are behind on their payments compared to its typical subprime borrowers, apparently not earning enough to cover the costs.

Both Uber and Lyft tell The Verge that the past year has seen a surge in public officials interested in giving the companies taxpayer dollars for public transit contracts. For the companies, it’s an appealing new way to establish themselves as vital infrastructure, especially in low-density communities like Altamonte where running traditional mass transit can be expensive. Given the pace at which these partnerships are coming together, it’s possible to imagine ride-hail companies taking on the role of all-encompassing, smartphone-driven public transit providers, one town at a time. ... The pilot program is unusable for people without a smartphone or credit card, and the company attempted to have the city sign an unusually far-reaching nondisclosure agreement. ... At a subsidy rate of 25 percent — and assuming the ridership would grow annually by 100 percent — Uber would receive roughly a million dollars per year from the city. A potential indication of Uber’s aspirations, the chart also included a scenario in which Altamonte would pay Uber a full 100 percent subsidy, putting the town on the hook for up to nearly $7 million in ride-share funding over a two-year span. ... Martz settled on a 20 percent subsidy for any trip within Altamonte, and 25 percent for rides to and from the city’s commuter rail station. Martz foresees the yearlong pilot costing taxpayers less than a hundred thousand dollars, far cheaper than building a new bus system. Nor does it involve navigating the regional transit authority or negotiating with potentially unionized public employees.

Under Cheng, Didi has expanded in just four years to 400 Chinese cities. The service lets users digitally hail and pay for taxis, private cars, limousines, and commuter buses. Cheng says 80 percent of all taxi drivers in China now use Didi to find passengers. So many people use the app, it can be difficult to get a cab during rush hour without it. Investors recently valued Didi at $35 billion, making it one of the most valuable private companies in the world. Uber, with operations in almost 500 cities on six continents, is worth $68 billion. ... Cheng was born in Jiangxi province, a landlocked region in eastern China famous for being the cradle of Mao Zedong’s Communist revolution. His father was a civil servant, his mother a mathematics teacher. He says he excelled at math in high school but during his college entrance exams neglected to turn over the last page of the test, leaving three questions blank. He got into the Beijing University of Chemical Technology, less prestigious than the upper-echelon schools. ... it turned out that Didi had a few advantages over the competition. Some were copying Uber’s U.S. strategy of working with limousine and town car chauffeurs. But there are far fewer black cars than yellow cabs in China. ... Instead of imitating competitors and giving away smartphones to drivers, an expensive proposition for a capital-strapped startup, they focused on providing their free app to younger drivers who already had phones and were likely to spread the word about Didi.

Self-driving technology has become a fixation for Kalanick. Developing a driverless car, he’s often said, is “existential” to Uber. If a competitor managed to get there first, it could easily replicate Uber’s core service (shuttling passengers) without its single largest cost (paying drivers). ... According to the legal complaint filed on behalf of Google’s driverless car division—as almost everyone at Waymo still refers to it—the company began investigating Levandowski last summer after learning that Uber had paid about $700 million for his months-old company. Google’s suit, filed in a San Francisco federal court, says its investigators uncovered a trove of digital evidence that hint at an unprecedented theft. According to the suit, Levandowski used his company laptop to download 14,000 design files from Google’s car project. ... At issue is a business that both companies believe will be worth hundreds of billions or even trillions of dollars a year. And though both companies like to portray driverless cars as some near-term inevitability, this dispute shows just how messy the race to get there could prove to be.