WEARING leg irons and guarded by federal agents, David Whitaker posed as an agent for online drug dealers in dozens of recorded phone calls and email exchanges with Google sales executives, spending $200,000 in government money for ads selling narcotics, steroids and other controlled substances.
Over four months in 2009, Mr. Whitaker, a federal prisoner and convicted con artist, was the lead actor in a government sting targeting Google Inc. that yielded one of the largest business forfeitures in US history.
"There was a part of me that felt bad," Mr. Whitaker wrote in his account of the undercover operation viewed by The Wall Street Journal. "I had grown to like these people." But, he said, "I took ease in knowing they knew it was wrong."
The government built its criminal case against Google using money, aliases and fake companies - tactics often used against drug cartels and other crime syndicates, according to interviews and court documents. Google agreed to pay a $US 500 million forfeiture last summer in a settlement to avoid prosecution for aiding illegal online pharmaceutical sales.
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Google acknowledged in the settlement that it had improperly and knowingly assisted online pharmacy advertisers allegedly based in Canada to run advertisements for illicit pharmacy sales targeting U.S. customers.
"We banned the advertising of prescription drugs in the US by Canadian pharmacies some time ago," the company said in its sole comment on the matter.
"However, it's obvious with hindsight that we shouldn't have allowed these ads on Google in the first place."
The half-billion dollar forfeiture, although historically large, was small change for Google, which holds $US 45 billion in cash. But the company's acceptance of responsibility opened the door to potential liability for taking ads from other people involved in unlawful acts online, such as distributing pirate movies or perpetrating online fraud.
Google has long argued it wasn't responsible for the actions of its more than one million advertisers. But the forfeiture paid by Google represented not just the money it made from the ads, but also the revenue collected by illegal pharmacies through Google-related sales.
In an important shift, the settlement "signals that, where evidence can be developed that a search engine knowingly and actively assisted advertisers to promote improper conduct, the search engine can be held accountable as an accomplice," according to Peter Neronha, the lead prosecutor.
Unknown is whether the company will toss aside advertisers as a result. "If Google were to adopt a much more restrictive definition of problematic advertisements, everyone would immediately notice a drop in their revenue," said Eric Goldman, director of the High Tech Law Institute at Santa Clara University.
The government's case also contained potentially embarrassing allegations that top Google executives, including co-founder Larry Page, were told about legal problems with the drug ads.
Mr Page, now Google's chief executive, knew about the illicit conduct, said Mr Neronha, the US attorney for Rhode Island who led the multi-agency federal task force that conducted the sting.
"We simply know from the documents we reviewed and witnesses we interviewed that Larry Page knew what was going on," he said in an interview after the August settlement.
Mr Neronha declined to detail the evidence, which was presented in secret to a federal grand jury. Other people familiar with the case said internal emails showed Sheryl Sandberg, a former top Google executive who left in 2008 for Facebook Inc, had raised concerns about the ads.
Prosecutors could have used that evidence to argue Google deliberately turned a blind eye to lawbreaking to protect a profit stream estimated by the government in the hundreds of millions of dollars.
Ms. Sandberg declined to comment through a spokesman. Mr. Page also declined to comment.
"We ban not just ads but also advertisers who abuse our platform, and we work closely with law enforcement and other government authorities to take action against bad actors," said Kent Walker, Google's general counsel.
Mr Whitaker's story, told here for the first time, presents a different picture. Shuffling into federal court in handcuffs and beige overalls last month, the 37-year-old prisoner looked like he could pass for an employee of a Silicon Valley start-up.
'It was very obvious to Google that my website was not a licensed pharmacy,' said David Whitaker, the prisoner who acted in the sting.
The Tennessee native suffers from bipolar disorder, according to court submissions by his lawyers, and has a history of manic spending and fraud sprees. When he was 16-years-old, Mr. Whitaker took his mother's credit card, rented a private jet and flew his girlfriend for a shopping spree in Knoxville, the documents said.
Mr Whitaker's path to undercover operative began in 2005, when he took millions of dollars in orders for Apple iPods and other electronics at below market prices and skipped town without filling the orders, according to his account and court documents. He hopscotched around the US in a private jet, evading arrest and protected by a private security detail. He briefly rented a Miami mansion for $200,000 a month.
He fled to Mexico in 2006 and started an Internet pharmacy, selling steroids and human growth hormone to US consumers through Google ads, he said. The two substances sold in the US by prescription only are sought by body builders to add muscle and by older consumers seeking to slow the signs of aging; they aren't approved in the US for such uses. Google's policy prohibited advertising their sale online.
"It was very obvious to Google that my website was not a licensed pharmacy," Mr. Whitaker wrote to the Journal. "Understanding this, Google provided me with a very generous credit line and allowed me to set my target advertising directly to American consumers."
Mr Whitaker was arrested in Mexico in March 2008 for entering that country illegally and returned to the US to face charges of wire fraud, conspiracy and commercial bribery in the iPod case. Mr. Whitaker told US authorities about the alleged role Google played in helping his Mexico-based pharmacy.
Federal prosecutors, seeking to test the allegation, set up a task force in early 2009 with Mr. Whitaker's help. On weekdays, he was escorted from the Wyatt Detention Facility in Central Falls, Rhode Island, to a former school department building in North Providence, R.I. There, under the watch of federal agents, he set a snare for Google.
Posing as the fictitious Jason Corriente, an agent for advertisers with lots of money to spend, Mr Whitaker bypassed Google's automated advertising system to reach flesh-and-blood ad executives. Federal agents created www.SportsDrugs.net, designed to look "as if a Mexican drug lord had built a website to sell HGH and steroids," Mr. Whitaker said in his account of the sting.
Google first rejected it, along with an anti-aging website called www.NotGrowingOldEasy.com. But the company's ad executives worked with Mr. Whitaker to find a way around Google rules, according to prosecutors and Mr. Whitaker's account.
The undercover team removed a link to buy the drugs directly - instead requiring customers to submit an online request form and Google approved it.
"The site generated a flood of email traffic from customers wanting to buy HGH and steroids," Mr. Whitaker said.
To pay Google's fees for the growing online traffic, undercover agents made payments every two or three days with a government-backed credit card.
Federal agents grew more brazen. They created a site selling weight-loss medications without a prescription, according to Mr. Whitaker and people familiar with the matter. They also added another site selling the abortion pill RU-486, which in the US can only be taken in a doctor's office.
Google's ad team in Mexico approved the site, so US consumers searching for "RU 486" would see an ad for the site. Google ad executives allowed the agents to add the phrase "no prescription needed."
Days later, federal agents added links to buy the drugs directly. Such sales broke US laws prohibiting the sale of drugs from outside the country and without a prescription. "There were photos of the drugs, descriptions, labels that clearly printed out that we were shipping without a prescription and it was from Mexico," Mr Whitaker said.
By the end of the operation in mid-2009, agents were buying Google ads for sites purportedly selling such prescription-only narcotics as oxycodone and hydrocodone. Agents also got Google's sales office in China to approve a site selling Prozac and Valium to U.S. customers without a prescription.
"Google's employees were instrumental in bypassing policy regarding pharmacy verification," Mr Whitaker told the Journal. "The websites were blatantly illegal."
At the agents' direction, Mr Whitaker said he signaled his illegal intent to Google ad executives, including Google's top manager in Mexico. As a tape recorder ran, he walked Google executives through the illegal parts of the websites. He said he told ad executives that US Customs had seized shipments, for example, and that one client wanted to be "the biggest steroid dealer in the United States."
Agents at first ignored the flood of orders. But as the ersatz sites morphed into full-fledged Internet pharmacies, they worried that clients, some sick, would be expecting medication.
So customers were told they had to become members by filling out an online form and to receive a "membership kit." The kits never arrived, but it stopped users from placing orders, Mr Whitaker said.
In the summer of 2009, US agents visited Google's headquarters in Mountain View, California, to tell corporate executives about the evidence they had collected. Prosecutors served grand jury subpoenas and eventually collected four million pages of internal emails and documents, as well as witness testimony.
The federal task force, which also included the Food and Drug Administration's Office of Criminal Investigation, was preparing criminal charges against the company and its executives for aiding and abetting criminal activity online, prosecutors said.
Google hired attorney Jamie Gorelick, the former deputy US Attorney General under President Bill Clinton. Two years later, the company reached a settlement with the government, a decision that stopped the likely introduction of emails to top Google executives had the case gone to trial.
"Suffice to say this was not two or three rogue employees at the customer service level doing this on their own," said Mr Neronha, the U.S. attorney. "This was corporate decision to engage in this conduct."
Six private shareholder lawsuits have so far been filed against Google's executives and board members, alleging they damaged the company by not taking earlier action against the illegal pharmacy ads.
Google has other potential legal exposure. Record companies and movie studios say Google willfully profits from illegal Internet piracy - an issue raised last week, when Congress dropped antipiracy legislation after opposition from Internet companies, including Google.
A 2011 study commissioned by NBC Universal estimated that nearly a quarter of all Internet traffic relates to pirated movies, TV shows and games. "There's big business in being agnostic about what sites you place your ads on," said Jay Roth, national executive director of Directors Guild of America, which backed antipiracy legislation.
Online scams pose another potential legal threat. Searches relating to mortgage refinancing have been among the most popular on Google, Eric Schmidt said in 2009 when he was chief executive. An investigation by Consumer Watchdog, a consumer advocacy group, found that a large number of companies selling "mortgage modification" on Google bore the hallmarks of fraud.
The special inspector general's office for the Troubled Asset Relief Program in November said it had shut down 85 alleged online loan modification schemes that defrauded homeowners through Google ads.
"Google has a natural long-term financial incentive to make sure that the advertisements we serve are trustworthy so that users continue to use our services, and we aren't afraid to take aggressive action to achieve that goal," the company said.
To end the sting, federal agents killed off Mr Whitaker's fictional character. They sent the Google employees a final email, allegedly from Jason Corriente's brother, saying the online entrepreneur died in a car crash.
Mr Whitaker, who pleaded guilty and faced a maximum 65-year prison term, was sentenced in December to six years, following what federal prosecutors called "rather extraordinary" cooperation. He is due for release in two years.
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