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I legitimately think the phrasing on this one is wrong if you're expecting unchecking it to be the way to avoid a dark pattern. The follow-up explanation is written as though there's a double negative, but there isn't one here.
That being said, Matz also isn't a fan of static typing. Static type annotations exist in the form of RBS, but no one that matters in the Ruby eco-system is pushing static type annotations in .rb files themselves.
Also, after seeing TypeScript, I'm very happy about that.
I myself am unsure where I stand on RBS. I wouldn't mind more use of it in my gem dependencies, but would probably not like it if it was enforced everywhere.
For now I'll stick with improving my test/spec-writing skills, and maybe some runtime type checking like https://literal.fun/
I think RBS is a decent tool, I don't mind it as long as it never becomes a requirement for anything. I hate the trend of statically typed dynamic languages because it's all of the pain without the main benefit (native speed).
I set this up for my daughter on her MacBook, and she quite enjoys the custom cursors. It definitely requires some technical expertise even after installing the app though, as it doesn't ship with extra cursors; you have to configure them yourself.