Earlier quoted context omitted.
I would claim the dictators -- even the "benevolent" ones--tend to do this more often than committees, as they have more inherent power to do so: the committees tend to get stuck in backwards compatible land forever (for better or for worse). I mean, look at Larry Wall or Guido Van Rossom with their respective debacles. Bjarne Stroustrop couldn't mess up in that way even if he seems to want to. As another example, HT…
Which Guido van Rossum debacle are you referring to? I can't think of one where he unilaterally caused a mess by dictating a hampered "second system" into life, as your comment seems to imply, but may just me misunderstanding or being ignorant. The closest thing I can imagine is where he actually resigned as benevolent dictator after having to meditate the walrus operator design committee/community, which is not a go…
I dunno... maybe read this? (edit: I forgot to add the link, lol; I have now added it ;P.) If you weren't there at the time, maybe it is easy to pretend none of this had happened, but it was a super big deal and there were the same kinds of bullying campaigns to get people to upgrade even when stuff was clearly slower and more broken and you knew it would become easier to port later.
https://gregoryszorc.com/blog/2020/01/13/mercurial%27s-journ...
Frankly, it all started to finally turn around in the Python 3.3-3.7 timeframe, with the biggest turning points being 3.6/3.7, which is when Guido finally was cracking under community pressure against his agendas and decided to start forming a committee to manage the language, before stepping down... until just now I hadn't realized that that was probably the thing that truly saved that language.