I never really got the "Worse is Better" essay. It obviously doesn't mean what everyone says it means and what it does mean isn't clear. This post points some of that out. For example, Worse in the essay was associated with simplicity. But the classic examples of Worse triumphing in the marketplace (the OP cites x86 as an example) are anything but simple: they are hypercomplex. Not only that, their complexity is largely what makes them Worse. Simplicity is rather obviously Better, not Worse. Smalltalk (which the OP cites as Better) is far simpler than its more successful peers. The more you look at the original essay, the more its conceptual oppositions seem muddled and at odds with history. I've concluded that it boils down to exactly one thing: its title. "Worse is Better" is a catchy label that touches on something important about technology and markets and means different things to different people.