My Favorite Wiretappers

We're so used to the idea that our telephones and computers can be tapped at any time that we forget things haven't always been this way. There was a 30-year window of time between the widespread adoption of the telephone in the late 19th century and the legalization of wiretapping in criminal investigations. It took a splashy Supreme Court case in 1928 -- full of Seattle-area bootleggers and one early radio star -- to convince the public and the justice system that wiretapping was a "reasonable" form of search and seizure and therefore didn't violate the Fourth Amendment.

Think about it -- for three decades in the early 20th century, it wasn't legal for the coppers to tap your telephone. You could call your fellow revolutionaries in the socialist party and chat about taking over the government without worrying that some dork would misinterpret your discussion as a terrorist plot and arrest you. And you could make plans for serious bootlegging over the phone, which is a convenient way to communicate when the police aren't allowed to listen in.

That's exactly what Roy Olmstead thought back in the prohibition era. A former police officer in Seattle who came to be known as "King of the King County Bootleggers," old Roy wasn't one of those small-time liquor-pushers with a still in his backyard. He used newfangled widgets like telephones and radios to create a global, black-market moonshine-smuggling service. He had boats and automobiles (more modern gadgets!) and thousands of happy customers. When he married his second wife, Elsie, he got the idea to set up a radio station in their mansion (built with liquor money of course). KFOX was Seattle's first commercial broadcasting studio, and Elsie was the darling of the local radio waves. She had a children's show featuring bedtime stories that were supposedly laced with covert references to drop-off points for rumrunners.

Eventually, Roy's operation and Elsie's radio show got so big that the police were bound to take notice. But Roy was smart enough that they couldn't seem to get any hard evidence on him -- they needed to catch him in the act, and it just didn't seem possible. So they attached a device to the copper telephone wires leading into his house, and tapped his phone. That's when the law nailed the Olmsteads. They recorded several conversations between Roy and his colleagues that made explicit reference to the bootlegging business.

Roy didn't give up, though -- he claimed the wiretap evidence was inadmissible because the tap was an "unreasonable" search of his house and therefore violated the Fourth Amendment. Because telephones were relatively new technology -- they were about the same age as the Internet is now -- nobody was really sure if Roy's attorneys were right. The case climbed all the way up to the Supreme Court in 1928. And that's when Olmstead v. United States changed forever the way we think about telephones. You know what happened: The justices decided wiretapping was a reasonable form of search, and Roy went to the pen for four years.

Seventy-six years later we're asking ourselves the same questions about the Internet. What exactly is a "reasonable" search of somebody's electronic data? Are you violating people's privacy if you look at the headers of their e-mails but not the bodies? Is it OK for your ISP to keep records of where you go on the Web?

One group, the Open Net Initiative (, is trying to answer some of these questions by taking a hard look at how Internet surveillance works throughout the world. ONI brings together people from Harvard Law School, the University of Cambridge, and the University of Toronto to tackle the related problems of Internet filtering and tapping. John Palfrey, executive director of Harvard Law's Berkman Center for Internet and Society, said ONI is using Net surveillance techniques to spy on the spies.

The group is tracking how Internet filtering technologies -- such as those used in libraries to prevent people from looking at offensive materials -- are used in countries like China to block Web sites deemed subversive by the government. Filtering programs can also track who is trying to visit the sites and keep tabs on anyone attempting to gain access to forbidden information. Censorship and spying are thus achieved in one fell swoop. "We watch to see when a site's traffic is being blocked, or when people's e-mail doesn't get through for political reasons," Palfrey said. He added that countries with political filtering schemes often buy the software and hardware to implement it from the United States.

As Roy and the heavily filtered Chinese dissident group China Labor Bulletin found out, the future of telecommunications technology is practically inseparable from the future of wiretapping. Next time you're feeling lonely online, just remember that somewhere out there, somebody is probably listening.

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