According to CNet’s Stefanie Olsen, Microsoft is reportedly in discussions to buy Claria, the notorious firm responsible for many of the unwanted pop-up ads and malware infections that are battled by consumers the world over.

According to BitsofNews.com, this move “underscores just how eager Microsoft is to catch up with Google, the search and advertising giant.” Eager?!?! How about desperate? Picking up Claria for its advertising network is like buying a nuclear test site because the lack of anything standing affords a great view of the mountains. Just ignore the 3-headed rabbits populating the poisoned ground and you’ll be fine.

There are plenty of other ad networks out there, most of which got to be successful without engaging in deceptive, unfair, and tortious activities.

Claria is a long-standing pariah among consumers, and its advertising reach is directly tied to its years of distributing malware and encouraging abusers to taking advantage of security holes in Microsoft’s operating system to install the software surreptitiously and without permission. Claria claims to be migrating its business model to one focused on more legitimate forms of business. But like the Gotti family and their garbage hauling business, it’s going to take them some time to stop living off their “other” gigs.

To get an idea about how brazen Claria is these days, you really need to check in with Ben Edelman, who is doing yeoman’s work tracking the malware industry. His analysis of Ezone.com gives you an excellent example of how Claria takes advantage of inexperienced users to get their malware installed on the computers of unwitting consumers.

Dan Gillmor has also done an excellent job of encapsulating the Valley’s thoughts on Claria in his posting this morning. As he notes, neither company would be enhanced by a union. Although, as I will explain, I think it may actually be a better match than you might think.

When I served as an expert witness for a group of a dozen companies suing Claria, I learned a lot about their business practices. Unfortunately, I can’t really talk about any of the juicy details that I learned. Suffice to say, there was ample evidence in the record to make it worth Claria’s while to settle those suits — which they did last year.

Over the last several years, I’ve also had the opportunity to work fairly closely with executives at Microsoft on a number of issues related to privacy, security, and spam. While I have known a few really wonderful people who have passed through the doors at Microsoft, I’ve also found that in far too many instances, seeing a lengthy stint at Microsoft on someones bio is an all-too-reliable warning sign of someone you shouldn’t turn your back on.

Too many of my experiences with those who have risen to executive positions at the Redmond giant, and those alumni who have since moved on to build their own ventures, have been marked by bald-faced dishonesty and an utter vacuum when it comes to issues of ethics and honor. And the infection doesn’t stop there. I’ve learned that when Microsoft inserts its tentacles into various “independent” organizations, it has had remarkable success in driving out anyone with principles and stacking the organization with bought-and-paid-for apologists.

Yes, yes, I freely admit that I’ve got a chip on my shoulder when it comes to the ways in which I’ve been screwed by Microsoft over the years. But I’ve also learned that there are two kinds of people in this community: those who have been screwed by Microsoft, and those who keep begging for it as long as the money keeps flowing.

The irony is that, putting together what I know about Claria with what I’ve I came away from my experiences with Microsoft, I think Claria would be an excellent fit for the Redmond culture.