I'm of mixed opinions about him. On the one hand, he's been influential in making Pycon more friendly to women, which I support[1]. On the other hand, he appears to have swallowed the feminist kool-aid without reflection. He has a knee-jerk reaction whenever an alleged case of "sexism" comes up - he is inclined to take the side of the "oppressed" group and facts be damned. He takes a guilty until proven innocent standard for people with a Y chromosome.
[1] The anti-harassment policies of Pycon are a gold-standard for the industry
That's why the "disheartening". He's obviously very smart and compassionate. I add a Code of Conduct to all my sites now, largely because of his example. The way he flew off the handle so quickly without taking the time to understand first really bothered me.
He was part of pronoun-gate? That was one of the stupidest, most counter-productive brouhahas of all time. Something tells me that purging your best devs for being insufficiently progressive is not going to attract more females.
Alex Gaynor was the catalyst for pronoun-gate, and reflects a prevailing attitude among a large number of the founding and old-school Django developers. I had the privilege to meet them and spend some social time with them at a past PyCon and I saw some of the attitudes firsthand, but they were remarkably more muted and respectable in person. Online, well...
So he's a flawed human being who makes mistakes just pg and the rest of us. What really is scary to me is the group dynamic that has come out of this "social justice" movement in that it seems to fueled by very loud public commentary about very small events. The pronoun incident with libuv really just took this to level of absurdism.
I blame it on universal college education. At least I ran into this stuff in college for the first time. SJW stuff is too alien and strange for most people to believe without indoctrination. But now there is an audience demanding burning of sexists and racists, the definitions of which have been expanded to include any person of a non-protected class that mentions sex or race.
After reading his tweets, my opinion of Jacob Kaplan Moss is more unmixed. I would never want to work with him on anything, even something as small as a lemonade stand. Keep that SJW BS out of tech and in English departments on the East Coast, where it belongs.
[1] The anti-harassment policies of Pycon are a gold-standard for the industry