

Usage share of operating systems, 2009.
From
StatCounter.com
(and see their main site).
DOS and Windows, despite being harder to use than the Apple Mac, soundly defeated the Mac in sales in the late 1980s and early 1990s. By the mid-1990s, the competition was over. Microsoft had won. And it is still dominant today.
The paradox is not why the techies did not use the Mac (I used DOS because it had a command-line). The paradox is why ordinary corporate and home users did not buy the Mac, which would have made their lives much easier.
David Gelernter has an interesting theory in The Aesthetics of Computing, 1998 (Ch.2, "The Paradox of Beauty"). He suggests that Windows won because the Mac was too easy to use, at a time when computers were meant to be hard to use.
He makes the comparison with cars, where every advance in ease-of-use, such as electric starters and even closed tops, was resisted by the "macho" car culture, which preferred cars to be hard to use. We see this even today, where computerised control in cars is resisted especially by Europeans, who prefer to do by hand many absurd and tedious jobs - such as managing the clutch and engine speeds - that could easily be handled by a computer.
It could well be argued that even today, for most users Windows is harder to use than the Mac, and people who buy the Mac are being quite sensible.
For me, UNIX is easier to use than either the Mac or DOS/Windows because of its powerful programmable command-line. I didn't actually find the Mac easy to use, since it didn't allow me write short command-line scripts.
This leads to another reason why the Mac may have failed: It was too extremist in having (until Mac OS X) no command-line at all, and forcing you to use windows and menus instead of just having it as an option. The Mac had an extremist philosophy, whereas DOS/Windows and UNIX were more tolerant of multiple different styles of interface. I say that the Mac is a better user interface, but of course I'm saying (patronisingly) that it's a better interface for other people. I don't really believe it's a better interface for me.
So maybe the Mac lost because it lost the power users, who preferred UNIX and DOS throughout the 1980s. Not because they were being macho, but because no-command-line really isn't a good interface for power users.
However, the rest of the world can be accused of being irrational for following the power users' line.
Because the OS is so fundamental to all applications, there is a tendency to standardise on an agreed OS. This can be done 2 ways:
or:
In both cases, all applications run on a common platform.
The disadvantage of the 2nd case is that you are at the mercy of whatever the monopolist decides to give you.

Usage share of Web browsers, 2009.
From
StatCounter.com
(and see their main site).
Free enterprise works because competition leads to better products and better choice.
Sometimes, in rare circumstances, this doesn't work, and, for whatever reason, the market turns into a monopoly in which there is seemingly no competition.
For example, who outside Microsoft believes that Word, Excel and IE gained their dominance in the word processor, spreadsheet and browser markets (respectively) by simply being the best products? Rather, these products gained it largely because they came from the company that made the Operating System. No one else had a chance. The latecomer Internet Explorer's rapid and total defeat of the pioneer Netscape is just the most spectacular example of this. Once something is bundled with the OS, competition in that market segment is effectively over, no matter how much of a late entry Microsoft was.
There is a strong case that this is one of those situations where government should intervene to try to restore some competition in the industry.
But what should they do?