I think mathematicians looking at that expression would curl their lips in mild disgust, but also evaluate it to True.

I can think of some more interesting examples when it violates intuition gained from mathematical notation.

When looking at `a == b == c` we naturally assume that not only `a == b` and `b == c` but also `a == c` because equality is assumed to be transitive.

The problem is that in Python we can make `==` operator to do literally whatever we want, so in Python `==` doesn't have to be transitive.

You may argue that no reasonable person would define equality in such way that is not transitive.

To which I would reply that approximate comparison of floating point numbers looks perfectly reasonable to me.

    EPSILON = 10**-9

    class Foo:
        def __eq__(self, other):
            return other.bar - EPSILON <= self.bar <= other.bar + EPSILON

As someone who trained in mathematics, I would 100% say that mathematicians would evaluate it as true. It's not the cleanest way to write it, but intent is clear.