Kottke called Stallman's rider (the whole thing) "crazy and amazing". Then he quoted the parrot thing, probably because it tickled his fancy. I don't agree that that constitutes "ridicule", in Winer's words.
Kottke's chosen words aren't always meant negatively. ("Here's to the crazy ones...")
In Kottke's context, he's given a fair description: the rider is, objectively, quite peculiar and illuminating about Stallman's intense priorities. But whether a reader takes that as a reason to shun and ostracize Stallman, as with disrespectful 'ridicule', is up to the reader.
Do we think Kottke would counsel Stallman, if we were in some bizarro universe where Stallman sought others' advice, not to include those two paragraphs, because they're too ridiculous?
I think it's equally likely Kottke would chuckle and say, "the bit about the parrots is crazy and brilliant, better even than the Van Halen thing... move it up higher!"
Read Stallman charitably. Read Kottke charitably. Read everyone charitably.
This!
Always, every day. You might make the world a little bit better in the process, but you will make your life a good bit less stressful, just by being a bit more charitable, a bit less suspicious.
If this isn't ridicule, then what is?
I agree that "crazy" is not exactly high praise, but it's a very overloaded term these days. I don't think it's meant to be as mean as Winer and everyone else is taking it.