I'm not sure what a "big ass type system" is, and I disagree that the number of actual problems is trivial. However, I'm in no more position to say what Ruby should be than you are, and I'm sorry you're so opposed to static types that even attempting to support them is a minus in your book.

However, even with TypeScript ascendant, the vast majority of people programming JavaScript write vanilla dynamic JS. I don't think dynamically typed Ruby is ever going to die. Whether large enterprise codebases will standardize on requiring type signatures is a different matter, because the benefits always outweigh what downsides you see in static typing once you surpass a certain scale.