The only way one can defend the claim that "the best program will eventually win" is to define "best" as "the one that wins."

I have to agree, and your example of windows is an excellent one although I think most people who complain about it are just venting general frustrations about computers and attaching "Windows" as a focus. I find few people who actually hate Windows, most think MicroSoft is the be-all and end-all ... most, but not all. I find that those of us who have used computers long enough to remember the pre-MicroSoft days are much more likely to say we dislike MicroSoft and actually mean it quite literally. But that just adds support to your comment - most people who use computers have used MicroSoft products from the beginning and have always assumed that if MicroSoft wasn't the really very good then they wouldn't have become so big and because they believe that they support MicroSoft which makes MicroSoft get bigger - totally circular and all based on PR and marketing skills rather than real quality of product.

I still remember when it was extremely unusual for a computer to crash and when it did it was a either a hardware problem or you were running a very poorly written program - and operating systems simply did not crash ever - so yes, winning has nothing to do with being the best, and the most popular also has nothing to do with being the best.

[btw, I've worked with computer for 33 years now, started on mini-mainframes and mainframes long before anyone even thought a home computer was anything other than science fiction so I actually was working with computers when MicroSoft came on the seen and experienced the world of computers before MicroSoft.]