Julissa Brisman

Clicking on a link, Davis navigated to breaking news out of Boston: A masseuse had been shot three times on the 20th floor of a Marriott hotel. There was a blurry security-camera image of the man the press had already dubbed the Craigslist Killer, and below that a picture of the victim, a sultry-looking woman with long light brown hair. It was Julissa Brisman, a sweet, funny, street-smart 26-year-old with pouty lips and a serious Paris Hilton fixation who had recently quit Davis’ employ to go independent. She was one of the Manhattan Madam’s favorite girls.

“I was shocked, devastated, heartbroken, but I wasn’t surprised,” says Davis. “I told her to be careful. Craigslist is full of creeps.”

It was a simple idea that changed everything: a no-frills hippie flea market updated for the Internet age, a place to go to buy a toaster, rent an apartment, or score some meth and hook up with random strangers for the afternoon. It helped to nearly destroy the newspaper industry in America, and it transformed the sex trade. It began 14 years ago when painfully shy über-nerd Craig Newmark started an e-mail list publicizing tech-themed events and job opportunities in San Francisco. Soon Craigslist was everywhere, a self-governing global community of online buyers and sellers, a for-profit business that operated more like a public service. Today Craigslist is an indispensable resource for tens of millions of people worldwide: With 40 million posts a month and sites in 570 cities and 50 countries, it is one of the icons of Web 2.0, as recognizable a brand as Facebook or Google. Yet it only employs 30 people, and the whole operation is run out of a ramshackle Victorian house in the Sunset District of San Francisco.

One of the new media’s signature success stories, Craigslist symbolizes the possibilities of the brave new online world we’re still in the process of figuring out. “The Internet reminds us that people are basically trustworthy,” Newmark has said. But there’s a lot of wiggle room in that “basically.” Like all online community experiments over the past 20 years—from MySpace to Second Life—the site has a utopian side that leaves it open to any creep with a dark fantasy life. What’s terrifying about the Craigslist Killer is what he represents: how the Internet can make crime push-button easy, and unlock psychosis as easily as libido.

Which is why the brutal murder of Julissa Brisman capped a perfect storm of negative publicity for the embattled Web site. Bad enough that the killer used the Erotic Services section to lure Brisman to the crime scene, but this wasn’t his first time. Four days earlier he allegedly tied up and robbed another masseuse he’d contacted through Craigslist, Trisha Leffler. And two days after the Brisman slaying, he allegedly struck again, this time in Warwick, Rhode Island, holding at gunpoint a stripper who advertised lap dances on Craigslist. The assailant fled only after the stripper’s husband burst into the hotel room.

Police arrested Phillip Markoff (left). Cameras at a Boston Marriott caught footage (right) of Julissa Brisman's alleged killer.

Boston cops quickly arrested Philip Markoff, a tall, blond, and outwardly respectable 23-year-old med student at Boston University who fit nobody’s profile of a serial sicko (see below). He was charged with Brisman’s murder in addition to the assaults on the two other women. Investigators searching Markoff’s apartment found a gun hidden in a hollowed-out book, a stash of hand restraints, as well as 16 pairs of women’s panties under the bed. (It’s not yet known how many times Markoff may have struck, but as Kristin Davis points out, many Craigslist sex-related crimes are never reported out of fear and embarrassment.)

The Craigslist Killer fits a disturbing pattern: The month before, New York radio reporter George Weber was stabbed 50 times, allegedly by a troubled teenager he met through a Craigslist posting offering $60 for rough sex. In April chubby-faced teenage misfit Michael Anderson was sentenced to life in prison for the shooting death of 24-year-old Katherine Olson, a Minnesota preacher’s daughter who had innocently replied to a fake ad Anderson placed on the site looking for a baby-sitter.

The bad news for Craigslist mounted. Also in April authorities arrested 24-year-old Shawn Skelton in Kent, Washington after he allegedly posted a Craigslist ad titled “A strange desire,” looking for a woman to have sex with and then kill. And in early May convicted sex offender John Steven Burgess pleaded guilty in Los Angeles to involuntary manslaughter in the death of 19-year-old Donna Jou. Burgess said he plied Jou with alcohol, cocaine, and heroin after meeting her on Craigslist, then dumped her body in the ocean when she overdosed.

Adding to the pressure on the company, in early May South Carolina attorney general Henry McMaster threatened the prosecution of Craigslist CEO Jim Buckmaster for facilitating prostitution. This was the first time a law enforcement official had tried to hold Buckmaster personally responsible for the criminal activity associated with the Web site. Craigslist was being attacked from every direction.

There have always been criminals willing to exploit the latest advances in technology, but the crimes linked to Craigslist of late have become increasingly frequent and bizarre. From murderers, rapists, and child molesters to flimflam men and blackmailing femme fatales, the site stars a cast of characters straight out of a James Ellroy novel.

Trusting strangers is the basis of Craigslist. It’s one big communitarian experiment, all very admirable, except for one thing: The ability to connect vast numbers of strangers to one another is only a good idea if the people being connected are decent human beings.