As someone who is a former Windows programmer, a Wine hacker and a security expert, I cannot escape the notion that many of Windows security weaknesses are a direct result of a deliberate design decisions made by Microsoft. This is not to say that Microsoft maliciously designed the entire system, starting with the API, going through the security and users system, and ending with the program features, based solely on "usability" and "convenience", with "security" either being discarded as unimportant or not being considered. Either way, it appears to me that many of the design decisions behind the way Windows were poorly made, security wise.
One of those rare Great Posts on Slashdot... An argument backed by facts and features not widely known in the GroupThink