Arguably those redesigns might have happened if the Python 2->3 transition hadn't received a decade of extremely vocal pushback

What’s funny is the breaking change that caused us the most headaches with 2->3 was the changes to fucking print.

I’m still finding broken print as a statement instead a function issues in codebases, somehow.

It’s the easiest one to fix, though. 2to3 does it easily. If it were the only change, we would not be having this conversation. It might have even not deserved a major version bump (given that even minor releases of Python don't conserve backwards compatibility).