Last week, "Internet marketer" Scott Richter got off with a slap on the wrist in one of the most high-profile spam cases in recent months. New York attorney general Eliot Spitzer sued Richter, president of OptInRealBig.com, back in December for sending deceptive junk email, and promised to seek millions in damages. But in a somewhat mysterious move, Spitzer wound up offering a settlement in which Richter paid only a $40,000 fine plus $10,000 for legal fees. Richter will also have to provide Spitzer's office with copies of all emails that he sends out in the future.

In this case, OptInRealBig served as a middleman between an alleged spam company called Delta Seven Communications and another company called Synergy6. Experts have speculated that Richter's middleman status made it hard to prove that his company had been spamming. Cases against Delta Seven and Synergy6 are still pending.

Also still pending is Microsoft's parallel suit against Richter, which also accuses him of spamming. Of course, Microsoft's motivations for suing Richter are probably more complicated than outrage on behalf of all those poor HotMail and MSN users who had to wade through his alleged spam.

You see, Microsoft is using Bonded Sender, a program that would supposedly separate "legitimate" Internet marketers and bulk mailers from spammers. Working with a California company called IronPort, Microsoft will gain access to a white list of bulk mailers who have paid a fee and demonstrated that they have no record of spamming. Companies participating in the Bonded Sender program will be allowed to send their email ads to HotMail and MSN users, along with thousands of other ISPs.

Given Microsoft's investment in IronPort's Bonded Sender program, it seems they may soon be in the business of serving as middlemen between email marketers and their webmail users. In other words, it sounds like the software megacorp is about to start competing with Richter. Of course, Microsoft could always call off its suit if Richter claims to have been rehabilitated -- especially if he manages to become a Bonded Sender!

In the spam wars, sometimes it's hard to tell the spammers from the antispammers.

The situation gets even more complicated when you consider the fact that IronPort does more than pick and choose winners in the junk email business. Bonded Sender will punish most the people who aren't even sending advertisements -- groups like Internet activists MoveOn.org, who send out millions of emails to alert their members to upcoming political events and issues. If these groups don't pay their Bonded Sender fees, ISPs like HotMail will likely spamblock their email -- regardless of whether users have specifically opted in to receive it. When it costs money to "go legit" as a bulk mailer, the biggest losers won't be people like Scott Richter. They will be nonprofit organizations, activists, and individuals who rely on email lists to talk to their communities.

[This post was modified slightly on 8/3/2004.]