If you're willing to play the "in this market segment" game, you can make anybody a winner. OpenBSD totally has a lock on the "paranoid dudes in their mom's basement who think Debian is too damned corporate" market segment.
The PC dominates overall because it is a generic business machine. But can you say the same about cellphones?
I think you can. "A generic mobile device". There, I said it.
The PC, in hindsight, I think was obviously a case of fully proprietary (Apple) vs. mostly open (the PC, with DOS and later Windows). One can easily say, "It's the applications!" And you'd be right...but why were there more apps for PC than Mac? Bigger market, sure. But, if Apple could stop people from making applications for the Mac, and Microsoft couldn't, I know which OS I'd be developing for. And that's the situation here. Apple are basically being bastards to their customers and their developers, and because Apple products are really attractive, extremely well-executed, and generally good and useful, people haven't immediately noticed what a bastard Apple is being about the whole thing. But, I think Matt's right. People will notice that Apple is treating them like crap, with abusive contracts, abusive terms for distribution of applications, and anti-competitive practices with regard to who gets to make and sell apps for the iPhone. It's already happening, and Apple will either wise up, or lose out.
You could even say that with Vista's DRM, even the PC is heading that way, where the open platform will eventually be relegated to a niche enthusiast market.
Nobody is saying that Microsoft is open, or good for consumers. At least, I didn't take Matt's post to indicate that at all. He merely used the early PC vs. Mac war as an interesting historical precedent for what's going to play out in the mobile market and for the very same reasons: Cost, availability of apps, and control (i.e. who controls your device: you, or the manufacturer?).
I think the comparisons are pretty obvious and pretty difficult to argue against. The current behavior and direction of Microsoft (and its own historical abusive behavior) is irrelevant. Nobody is going to argue that the PC was a less open platform than the Mac in the 80s and 90s, and changes in the landscape since then don't alter history.
So it is easy to imagine the cell market being dominated by the most shiny thingy.
I think it'll be dominated by the cheapest thing that does what people want, just like PCs. It is becoming a commodity...as most mass-manufactured goods do.