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Operator overloading is bad in its own right, but it's a subclass of the larger problem here, which is the "well, if you squint a little, it kinda makes sense" approach to design.
I think this sort of thing survives for two reasons. First, because most languages evolve, and evolution is messy. Second, because nerds get a little dopamine hit every time they learn about a quirk like this -- they can use it to signal their superior command of the language.
One fateful day, a bored programmer thought, "What if I designed a language that was just quirks all the way down?" and Perl was born.
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