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"a hopeless optimist" is very funny!!!
I don't think Obama was aware of paradox inherent in the phrase (not because of he's not smart but because even intelligent people are often not adequately sensitive to the language).
It is lovely as well, especially in its context: That Obama would maintain his optimism in the face of what he's faced with such a pure phrase. I think it should stick to him . . . and for all of the right reasons.