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Wouldn't a guy retiring after winning a Cy or MVP constitute "going out on top?" I agree it's something that shouldn't happen very often (extremely rare, I would say - Koufax did it in real life, but that was related to arm troubles). That example almost refutes the "guys hanging around til the bitter end" argument (though have been some real life examples of that too - usually because a guy is close to a milestone).
I say almost because the hanging around til the bitter end seems to happen much more than it should.
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