That's a different question than "Has it confused a whole lot of high school students?"
"The misuse of the equality operator is only one minor detail, but if people care so little about such details, how can they be trusted to look after the more important ones?"
Assuming by "more important ones" you mean more important mathematical ones, that's extremely easy to answer: They can't and they haven't. Very few programming languages look anything like conventional mathematics. Most of the popular programming languages are wildly adhoc from a mathematical perspective. But while some mathematically-inclined folks consider that some sort of damning criticism, they must also address the fact that there are no known practically useful languages that are not at least partially adhoc. Haskell is the closest and the community is well-aware of the places where even it cuts substantial mathematical corners. However, the developing languages that don't cut mathematical corners are only useful on toy problems right now, with the occasional triumphant breakthrough on a very particular problem. It's hard to program in languages where successfully creating a "sort" algorithm is a modestly impressive feat.
Compared to the other wild liberties taken relative to conventional mathematics, rewriting two parallel horizontal lines to mean "assignment" is hardly even interesting... after all, assignment itself, as an operation embedded in time, isn't very "mathematical", requiring rather a lot of formal machinery to represent, and goodness help you if you try to formalize what a multi-core system is really doing. It's merely one of the more obvious deviations from math, but arguably the more numerous and profound subtle ones are much more important.
There isn't really anything more to debate. Your position appears to be that such details are "uninteresting", even for an aspiring high-level language like Python, because there are harder problems to solve. I suspect many academics would disagree, which I infer from their language designs.
I have no doubt that beginners soon learn any different meaning of "=" over time, but why reuse the operator in the first place? Is it really making it "easier" for the beginner? At least with BASIC the context switch was easier as it was strictly imperative. Python tries to mix in more declarative concepts.
The misuse of the equality operator is only one minor detail, but if people care so little about such details, how can they be trusted to look after the more important ones?