A gritty, ambitious fixture of the Connecticut Democratic Party for decades, Blumenthal, at 31, was the youngest U.S. Attorney in history when Jimmy Carter tapped him for the post in 1977. He made his name prosecuting drug traffickers and organized crime, and in 1990, he was elected attorney general, a position he would hold through four re-elections. In 2000, when Senator Joe Lieberman opted to continue his senatorial campaign during his vice presidential bid, it hampered Blumenthal's career trajectory—had Lieberman bowed out, Blumenthal was a shoo-in to become his successor in the Senate.

As it turned out, fate had other plans, and Blumenthal's ascension would have to wait. In the meantime, the man took on various crusades with a zeal that ingratiated him to law-and-order types and progressives alike. He banned ATM fees, sued Microsoft and Big Tobacco, and orchestrated a national campaign against misleading sweepstakes mailings. His enthusiasm for courting the national spotlight brought the occasional criticism of attention-seeking—"The most dangerous place in Connecticut is between Dick Blumenthal and a TV camera," quipped back in 2000—but he remained more or less a popular figure in his state. Currently, the tanned 63-year-old is laying the groundwork for a 2012 Senate run.

Rather than disregard the unassuming two-page letter on his desk that fall day, Blumenthal found a new cause at which to throw himself with characteristic vigor.

Cook County Sheriff Thomas Dart sued Craigslist, saying it facilitates prostitution
Courtesy Cook County Sheriff's Department
Cook County Sheriff Thomas Dart sued Craigslist, saying it facilitates prostitution
Connecticut Attorney General Richard Blumenthal has asked Craigslist to eliminate the Erotic Services category
Courtesy Connecticut Attorney General's Office
Connecticut Attorney General Richard Blumenthal has asked Craigslist to eliminate the Erotic Services category

"Every brick-and-mortar establishment has a responsibility to protect the safety of its employees, patrons and the general public," says Blumenthal. "And so too does an Internet site."

The first thing he did was fax Craigslist a short missive on Connecticut attorney general letterhead, as well as a copy of the irate mother's original complaint. "I am certainly concerned that children may have access to such explicit material," he wrote. "I would appreciate your review and response to the complaint, as well as any suggestions for improvement."

Twenty-four days after Blumenthal's first fax, an attorney for Craigslist replied with a four-page letter that effectively said, "Thanks, but no thanks." Lawyer Barry Reingold made clear that Craigslist officials sympathized with the woman's "desire to protect her children from personal advertisements that are intended for adult eyes only," but it was quite frankly out of their hands. He suggested that she install a web-content filter, which, he pointed out, is "freely available, easy to use and effective."

The law-and-order East Coast prosecutor and the Left Coast live-and-let-sin entrepreneurs couldn't have been cut from more different cloths. Blumenthal was a sergeant in the Marine Corps; Newmark adopted a purple peace sign as the logo of his company. Blumenthal, a Brooklyn native, hails from a well-to-do family and holds degrees from both Harvard and Yale; Newmark, a Jersey boy, is more humble in stature as well as pedigree, having earned his computer-science degree from Case Western Reserve University in Cleveland.

Over the course of the next several months, both factions bantered back and forth over conference calls, with Craigslist executives gradually growing more receptive to making some concessions. In early 2008, Newmark and Buckmaster agreed to amp up their enforcement of the site's terms of use and introduced a telephone-verification requirement. As a result, the number of posts for erotic services in Hartford, Connecticut, dropped from about 400 per day to 50, according to Craigslists's web metrics.

But when a Connecticut woman was arrested on March 19, 2008, for prostituting herself on Craigslist, Blumenthal jumped back on the case, livid that sex-worker ads were still polluting the site.

"I am astonished and appalled by Craigslist's refusal to recognize the reality of prostitution on its website—despite advertisements containing graphic photographs and hourly rates and widespread reports of prostitutes using the site," he wrote the company. "Craigslist must determine now what type of site it is. If it's truly concerned about the issue, it must devote resources and technology to eliminate these postings from its site."

Frustrated by what he perceived to be stonewalling, Blumenthal went public. In March, he appeared in the daily New Haven Register to accuse Craigslist of profiting from prostitution, and then laid into Buckmaster and Newmark for allegedly dragging their feet in implementing the agreed-upon changes.

Baffled, Craigslist brass went on the defensive and fired back on the site's blog. "We were disappointed that he chose to ignore our recent progress in dramatically improving compliance with our terms of use, shocked at the bizarre assertion that we are 'stonewalling,' and frankly stunned to hear Craigslist recklessly slandered as 'profiting from prostitution,'" wrote Buckmaster. "Craigslist will not be used as a punching bag for false and defamatory statements."

In July 2008, the sides arranged their first face-to-face sit-down. Buckmaster and two Craigslist attorneys made the cross-country trek to Rye, New York, just beyond the Connecticut border, halfway between Hartford and New York City. They met Blumenthal and a few of his subordinates in a coffee shop and, over the course of a few hours, hashed out an agreement.

Under the accord, Craigslist began asking advertisers to provide valid identification, in addition to charging Erotic Services advertisers a nominal credit-card fee ($5 to $10) per ad, enabling the company to confirm users' identities and establish a digital fingerprint. Craigslist also vowed to donate all profits from the sex category to various charities, particularly those that address child exploitation and human trafficking.

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