Unix, Linux and Java just to name a few highly successful worse is better paradigms. List the number of multi-billion dollar Lisp startups - I can think of only one that comes close - ITA ($700 million), and that was bought out by a C++/Java shop, namely Google.
The lisper follows up his essay with another: http://dreamsongs.com/Files/worse-is-worse.pdf (this IS written by Richard Gabriel, only under pseudonym, look at your wiki article: "Gabriel later answered his earlier essay with one titled Worse Is Better Is Worse under the pseudonym "Nickieben Bourbaki" (an allusion to Nicolas Bourbaki)." - last line of "Effects" section) which presents slightly different opinion :)
Also, I'm afraid Java is a perfect counterexample for "worse is better". It does everything and then some, but there are better (like, worse - less complicated, easier to use, more focused) solutions for almost everything Java does... And Java is still insanely popular.
Lastly, you seem to want to equate popularity with quality, and then you give Linux as an example. Surely, Windows is better because it's installed on many more PCs than Linux?
Worse is a fuzzy term - let's define it. Worse in this case means things that can be used by many average people to do the things that they want without mental contortions and actually ship useful products to billions people.
Java does that. Linux does that. Windows does that. Lisp doesn't.
And note - your article wasn't written by the author - it was written by someone else.
Ok, this is what I was asking at the beginning, writing the question: "In what sense?"
You're entitled to your own definition of words, in this case you defined "worse" (and this definition is very popular, too!) and it's ok. My perspective is different and so my definition is - I don't care about "average people" at all, I like very much "mental contortions" and I enjoy making more than shipping, and so "worse" for me means something different altogether.
I just wanted to what you meant by "worse", really. I won't agree with you here, but I understand and accept your opinion.
I edited my previous post in reply to your note at the end.
You'll notice that most successful systems empower the common man (or unit) (capitalism/democracy/distributed systems/self-policing/bottom up ideas) and the most "ivory tower"/"top down" like systems don't perform nearly as well (totalitarianism/communism).
There are limits of course, and always complexity, but distributed incentive based systems appear to empirically work rather well.