There's a difference between not being afraid of coming across as cringeworthy, and coming across as cringeworthy. The former doesn't ennoble the latter, and for someone who chose the role of not only originating ideas but seeking also to make them popular, the latter is a real problem.
A good point re him having two roles. Speaking your mind and expressing yourself freely are both paramount for a good thinker, while both are anathemas for anything that has to do with people’s opinion and politics. Maybe the two roles just don’t combine very well.
It might be similar to the concept of code-shifting in linguistics. That depends on the ability to "read a room", and whatever Stallman's virtues, that has never seemed to me to be among his skills.
To draw a comparison which will certainly infuriate everyone, Stallman might usefully be considered as a Wozniak desperately in need of a Jobs.
He's like Cassandra, except a tad insufferable instead of cursed.
Social skills are boring to work on, but he's a political activist; those should be a priority for him. He's usually right, but that doesn't mean he has to say things all the time! (Or, rather, he could probably pick more opportune moments, while retaining most of the frequency, and be listened to more.)
Plus, the kinds of jokes you make with your friends are not necessarily the kinds of jokes you should be making on stage, during a talk about free software, in front of a wide audience of strangers. Though I hear he's got a lot better at this in the last half-decade, so perhaps this criticism is no longer warranted.
His social skills are fine, and he has been immensely successful and changed the entire face of computing. I find it strange that people condescend about his appearance and manner because he has as of yet failed to transform the entire technological world to his vision.
The reason FOSS exists is because of how charming and convincing RMS was and is.
I condescend about his manner because when he slipped up, he slipped up big-time. Not just a single-word blunder, but entire paragraphs. (He does this less nowadays, from what I can tell.)
He was charming and convincing within the environments in which he needed to charm and convince people. I reckon those were largely informal settings, in what I've heard referred to as "tech-bro" cultures. Those skills don't generalise.
The easiest way for eccentric people to gain social acceptance is to fit in. That was never an option for Richard Stallman, so he must've been charming and convincing. I couldn't have done what he's done. That doesn't automatically mean he's good at every kind of social interaction – and he most certainly wasn't, in the early 2000s. He made enough public slip-ups that I might need two hands to count them!
He's a political activist. One slip-up is enough for your enemies to discredit you. He can't afford as many as he's made, and certainly not any more. That's why I say he needs to focus on social skills; there's still work to do, and he's still one of the few people doing it, and he needs social credibility to be able to do so.
(I suppose his biggest mistake was spreading himself across so many causes, and hence making himself a lot of enemies… But I'm not going to criticise him for that; it's better than I've ever done.)
> I condescend about his manner because when he slipped up, he slipped up big-time
In his failure he seems to have achieved success greater than pretty much anyone else in the tech industry. The GPL and the laughably successful strategy behind it is one of the main planks underpinning the modern tech industry, and Stallman was one of the key characters to set in motion that agglomerative process that is the modern OSS stack.
Stallman has arguably had a more transformative impact on the software industry than any CEO in recent history. It is a weak argument, because any one man can only do so much, but it is there. More than can be said about most people.
If that is his contribution with slip-ups you must have high expectations for him.
The slip-ups I'm referring to were largely spur-of-the-moment social blunders; there's only one general principle I know he has that I think is wrong. If he hadn't made those, there'd be less fodder against him, so he could do more. I'm glad he's not making them as much, but he's still doing it enough that he had to resign from the FSF to prevent it from being dragged down by association with him.
I haven't heard any “Richard Stallman ad-libbed one of his comedy skits badly and made members of the audience feel uncomfortable” stories since 2010 at the latest. I haven't heard he got better; I've just stopped hearing complaints. From this, I infer that he got better.
One of the more hidden benefits of people being more willing to raise concerns like this is that people bad at noticing that they're doing stuff wrong get told it – and then, if they care, they get better. (And if they don't get better, keep shaming them; even if they care, just caring isn't enough.)
I would rather people focused more on legitimate complaints like these, even though they aren't snazzy enough to make newspapers; making up stuff like “Richard Stallman supports child sexual abuse” helps nobody (except sensationalist newspapers, but they're not worth helping), whereas calling out the many small components of systematic injustices (e.g. many women feeling excluded from tech and hackerdom because they're women) helps many.
Well, I can attest from personal experience that he was still stuffing his foot in his mouth that way as late as 2016; I didn't leave the talk, but I saw enough people do so that it was clearly not by happenstance.
I've discussed the incidents of that talk before on Hacker News, at considerable length and in the face of the same anger borne of discomfited hero worship that seems to attend every criticism of Stallman's behavior. If you're interested in the details of that discussion, I'll ask you to find it in my comment history here, as I have occasions today both more urgent and more appealing than to attract yet another tiresome crowd of would-be shouters-down.
I remember back in the late 90s at one of (GNU/)Linux shows (was it in Paris?) RMS arrived and started singing this song, many people joined in marching, it was a very happy and positive event. Of course everybode knew it's a kind of joke, just like the whole St. iGNUcius thing, but at the same time the general idea of sharing the code with others as opposed to hiding it seemed quite serious and meaningful. And so it continues to this day.