ON FEBRUARY 25, 2009, a then 34-year-old career con man named David Anthony Whitaker left the Wyatt Detention Facility in Central Falls, Rhode Island, and slid into the backseat of an unmarked government car. He was dressed in traditional prison garb—khaki pants, brown shirt, handcuffs, leg irons. A federal agent sat beside him. A second car followed to make sure nobody trailed them or attempted an ambush. Not that anyone expected trouble. This was merely standard procedure when transporting a government cooperator.

That’s what Whitaker was now: a cooperator. It felt surreal. One year ago he was in Mexico, living the most fulfilling life he’d ever known in his chaotic, troubled years on the planet. He had been bringing in obscene amounts of money by selling black-market steroids and human growth hormone online. He had a multimillion-dollar apartment in a country club in Guadalajara. He had a cabin in the mountain town of Mazamitla. He had lots of cars—an orange 4Runner, a BMW, a Jeep. He’d even funded the construction of a local hospital. Sure, he had to live under an alias and was on the run from US Secret Service agents who were trying to nail him for a long-standing multicount fraud complaint. But he had a lawyer on retainer, and at least the local cops were easy to pay off.

That life ended on March 19, 2008, when a Mexican immigration agent nabbed Whitaker and brought him back to LAX, where the Secret Service promptly arrested him. He was facing a potential sentence of 65 years in prison. Sixty-five years. That meant spending the rest of his life behind bars. The thought was unbearable.

Whitaker began thinking of ways to knock years off his sentence. He considered providing the names of the drug users, pushers, and doctors who had patronized his online steroid business. They were mostly easy marks, and Whitaker was quick to take advantage of them. For a while he bottled sterile water in 1-milliliter vials, marketed it as a steroid called Dutchminnie, and sold it for $1,000 a pop. Not only did clients fall for the scam, they sent back photos showing how they’d bulked up after using the “drug.”

But he quickly realized that he could offer the government much more than the names of a few juicers. At one point during a meeting with Whitaker and his lawyer, the Feds asked him how he had grown his online enterprise. Whitaker’s answer was immediate: He had used Google AdWords. In fact, he claimed, Google employees had actively helped him advertise his business, even though he had made no attempt to hide its illegal nature. It was reasonable to assume, Whitaker said, that Google was helping other rogue Internet pharmacies too.

If true, this would be a bombshell. This was Google, after all. Since its founding, the search giant had prided itself on being a different kind of corporation, the “don’t be evil” company. And for almost as long, its open-to-all-comers ad policy had come under scrutiny. Online pharmacies were a particular sticking point; in 2003, three separate congressional committees initiated inquiries into the matter. On July 22, 2004, a month before Google went public, Sheryl Sandberg—at the time Google vice president of global online sales and operations—testified before the Senate Permanent Subcommittee on Investigations. Legislators had proposed two bills that would regulate online pharmaceutical sales, but Sandberg argued that the measures would be unduly burdensome. She said that Google employed a third-party verification service to vet online pharmacies. She also described Google’s own automated monitoring system and the creation of a team of Google employees dedicated to enforcing all of the company’s pharmaceutical ad policies. “Google has taken strong voluntarily [sic] measures—going beyond existing legal requirements—to ensure that our advertising services protect our users by providing access to safe and reliable information,” she testified. Neither bill made it out of committee. (Sandberg, now Facebook’s chief operating officer, declined to comment or be interviewed for this story.)

The agents seemed skeptical of Whitaker’s claims and spent the next 10 months following up on them. But they apparently found the story plausible, because now Whitaker was being driven to a Providence, Rhode Island, postal inspector’s office to launch the US government’s undercover investigation into one of the world’s most admired, profitable, and powerful companies.

As soon as they entered the postal inspector’s office, the Feds explained the ground rules. Whitaker had to be completely honest with them; one lie and any possible deal was off. From now on, he would be known as Jason Corriente, the fictional CEO of a fake Rhode Island–based marketing firm called Maxwell and Associates. The FDA had already secured an 800 number, a bank account, and an answering service. His job: to buy advertising for SportsDrugs.net, a website that sold HGH and steroids from Mexico, no doctor’s prescription required.

With his talent for prevarication, Whitaker was well suited to the task. Throughout his checkered past, he had assumed false identities, sold nonexistent products, and written bad checks. But he’d never faced such high stakes. If he couldn’t somehow lead Google into breaking the law again, he’d probably die in prison.

An agent handed Whitaker a list of phone numbers of Google employees and a phone hooked up to a recorder, then told him to dial.

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