Current Status: Ring-Tone Merchant
Scott Richter has never claimed to be anything more than a "high-volume electronic marketer" and, unlike many of our contenders for the spam crown, he's never spent a day in a prison jumpsuit. Yet spammish activities have cost him big in other ways. In 2005, he agreed to pay Microsoft US$7 million to settle a lawsuit over bulk e-mail sent by his company, OptinRealBig. The suit charged that OptinRealBig used fake subject lines and falsified addresses. He settled another suit brought by then New York Attorney General Eliot Spitzer and agreed to abide by federal laws concerning bulk e-mail. He even got himself removed from Spamhaus.org's Register of Known Spamming Operations (ROKSO), considered the authoritative source on junk e-mailers.
But in January 2007 Richter's new company, Media Breakaway, was sued for--yes--sending deceptive and unsolicited commercial e-mails to MySpace users. Last June, an arbitration panel awarded MySpace US$6 million in damages and attorneys' fees. The 41-year-old Richter also recently made headlines as one of the principals behind Ringaza.com, a site accused of charging customers US$7 to $10 a month for "free" ring tones.
Spam Royalty Rank: Raja of Ring Tones
Christopher William Smith
Current Status: Serving 30 Years in Big Sandy Prison, Inez, Kentucky
As proprietor of the Xpress online pharmacy, the 28-year-old Smith built up a fortune estimated at US$24 million by selling prescription drugs illegally across the Net. When FBI agents raided Smith's home in May 2005, they found a Lamborghini in the driveway and cereal boxes stuffed with more than $1 million in cash. But they didn't find Smith--he was already on the lam in the Dominican Republic. When he returned a few weeks later, he was arrested at the airport.
In November 2006, a federal jury convicted Smith on nine counts of drug running, wire fraud, money laundering, and racketeering. In a separate case, AOL sued Smith for sending billions of spam e-mails and won a judgment of US$5.3 million. But what earned Smith that 30-year stretch was even more special: While awaiting trial in March 2006, Smith was caught on tape ordering a hit on a witness's children from a jail-house phone.
Spam Royalty Rank: Prince of Pills