Not canon, of course, but I like the explanation in one of the novels that the "R" was some sort of personal insult Mitchell frequently used towards Kirk at the Academy.
James Retarded Kirk?
James Retrograde Kirk?
James Redneck Kirk?
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Mitchell: "No, really, it used to be 'R.' Wouldn't you change it to 'Tiberius' if your middle name rhymed with a part of the female anatomy?"
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