I have watched a ton of interviews with Jack and find him extremely inspirational and what he does (and has done) being truly amazing. Easily one of my favorite entrepreneurs to follow.
With Twitter, I get the sense he lost control of the company a long time ago because of a combo of monetization and culture.
So basically he helped build the greatest communication platform in the world and instead we get what Twitter is today.
This kind of weak Twitter Blue announcement, to me at least, just shows at what a lost the platform is for making money in a way that isn't engagement driven (aka, rewarding flaming-type behavior).