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Sam Gentile has a revelation while learning Python - and I think his explanation of his former bias explains a lot of how people talk past each other on dynamic typing:

VBScript, on the other hand, is a weakly typed language because you can concatenate the string '12' and the integer 3 to get the string '123', and then treat that as the integer 123, all without any explicit conversion. Also, unlike VBScript, Python will not allow you to reference a variable that has never been assigned a value. Then it hit me. I have been (naively) biased against late/dynamically bound languages because of the crap that is VBScript. This is coupled with Everything Is An Object. This is the kind of type system that has flexibility but certain safety at the same time and I can deal with that. It may not mean much to others but it unlocks a huge door for me.