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Google’s Web site acknowledges that it collects information about its users, but not names or other personally identifying information. It does, however, collect the names, credit card information, telephone number, and purchasing and credit history of those who sign up for such features as Google Checkout, a service that enables customers to make online purchases. In its five-page Checkout privacy policy, Google said that it may also “obtain information about you from third parties to verify the information you provide.” Google said it “will not sell or rent your personal information to companies or individuals outside Google”-unless individuals give their “opt in consent.” But even if consumers choose not to opt in, Google still retains a wealth of personal information, which it is free to use to better target search or YouTube advertising. This data, mingled with its search data and the data gathered by DoubleClick, induces privacy anxiety. Companies like eBay and Amazon.com, among others, also retain credit card and other personal information, but there is a difference: Google uses this data to assist advertisers, and eBay and Amazon do not have advertisers to assist.

This is where the specter of Big Brother enters the discussion. “In 1984, Winston Smith knew where the telescreen was,” observed Lawrence Lessig. “In the Internet, you have no idea who is being watched by whom. In a world where everything is surveilled, how to protect privacy?”

Big Brother comes in different guises. Under the federal Patriot Act rushed to passage after 9/11, the executive branch can, without a warrant or users’ knowledge, gain access to what Americans e-mail, search, read, say on the telephone, watch on YouTube, network with on Facebook, or purchase online. There are tens of millions of surveillance cameras on our streets and in buildings. Candidates for public office can be harmed by damaging leaks to reporters of the most private information, as nearly happened to Supreme Court nominee Clarence Thomas when his in-store video rentals were leaked, suggesting he was partial to pornographic films. Advertisers can pay Google and other companies to access better targeting data. Telephone or cable companies can offer free services in exchange for a record of a consumer’s every click, encoding the knowledge of every song they listen to, product they buy, ad they like. In recent years, AOL (among other companies) was publicly embarrassed when it extracted and shared the names of some users from the Internet protocol address found on every browser on every computer.

Google may be viewed with suspicion by many media industries, but it enjoys a well-deserved reputation for earning the trust of users. In its 2007 annual ranking of the world’s most powerful brands, the Financial Times and the consulting firm Millward Brown awarded Google a number one rating. Still it is hard to imagine an issue that could imperil the trust Google has achieved as quickly as could privacy. One Google executive whispers, “Privacy is an atomic bomb. Our success is based on trust.” The Interactive Advertising Bureau’s Randall Rothenberg employs a different image: “Privacy is one of those third rails with unknown amounts of electricity in it. People think about advertising and worry. That’s part of America ’s don’t tread on me attitude.” Yet Rothenberg is unsure about the amount of electricity in the privacy issue because he is acutely aware that Americans hold contradictory attitudes toward privacy; they tend to distrust governments, businesses, or advertisers that can spy on them, yet “if they really cared enough about privacy they’d never have credit cards. They’d never subscribe to cable TV” They wouldn’t parade their most private thoughts on Facebook. So how does a company like Google locate and not step on the third rail?

To find that third rail requires a degree of sensitivity not always found in engineers. Yet Google has at times been sensitive. When, in 2006, the Justice Department subpoenaed a number of Internet companies to turn over all child pornography search queries, Google, opposing the request as a “fishing expedition,” took the U.S. government to court and won. (The judge ruled that Google had to turn over fifty thousand suspicious URLs, but none of its user’s names.) “Unfortunately,” said Schmidt, “our competitors”-including Time Warner, Yahoo, and Microsoft-“did not hold the same position, and complied.” He is outspokenly critical of the Patriot Act, which he believes violates privacy and grants the president too much power. Schmidt implicitly agrees that privacy is a do-not-step-on third raiclass="underline" “If we violate the privacy of our users, then we’ll be hosed.”

Trust is essential to Google, as it is to much of modern commerce. If we didn’t trust waiters or Amazon, we couldn’t use credit cards. If banks didn’t trust that we’d pay back loans, they would not grant mortgages. Sergey Brin notes that users don’t like intrusive ads or junk mail, and Google deserves credit for siding with users against these, even sacrificing revenues to do so. From a user’s perspective, Google is not wrong when it says the more information it has about our search histories, the better the search results will be because it can anticipate a user’s intent. And it is also undeniably true that many users search the ads to comparison shop. “We think of the ad as content,” said Google’s vice president of engineering, Jeff Huber. The portrayal of Google as Big Brother frustrates people who work there. “It’s a fear of the possibility rather than the reality,” said Huber.

FEAR OF “THE POSSIBILITY” was enough to motivate privacy advocates. In May 2007, the Bush administration decided that the Federal Trade Commission (FTC), not the Justice Department, would look at whether the merger might violate antitrust laws, and the commission quietly began a preliminary investigation. Chester pushed for the FTC to broaden its probe to include privacy, and the agency scheduled a town hall meeting in November to explore those issues. “I got the hearing,” Chester boasted. “There’s nobody watching the store.”

Chester is not the stereotypical lobbyist, the ingratiator, the affable fund-raiser, the guy you’d join for a drink or a steak dinner at the Palm. Chester annoys people, concedes a senior FTC staffer, “but he is responsible for the hearing.” Chester helped persuade Democratic senators on the Judiciary Committee to conduct a one-day hearing in September 2007 focused on the merger and online advertising. Knowing that European governments have more stringent privacy protections, he urged the EU to hold up the merger until Google better explained its privacy policies. Chester stayed in touch with government regulators elsewhere. He filed additional complaints with the FTC. He had no expectation that the FTC would reject the merger. His best hope was that the FTC would compel Google to admit that its warehouse of data required more stringent privacy safeguards. Chester and Rotenberg were more hopeful that the European Union would reject the merger; and privately, Google officials conceded that an EU rejection would scuttle the deal.

By the end of 2007, it was apparent that privacy issues were gaining traction, spurred by a crescendo of news stories about real or potential invasions of privacy. Many were chilled when President Bush declared that under the Patriot Act he did not need judicial or congressional approval to wiretap the phones of anyone the executive branch suspected of consorting with, or knowing, alleged terrorists. It was revealed that telephone companies, at the request of the Bush administration but without court approval, turned over oceans of data concerning the phone calls and e-mails of individuals.