I would argue that Russia is in a better position to win tactically then the West is. They have the greater correlation of forces, and a shorter supply line. They also have the line in the sand in terms of what happens in terms of attacks on Russian soil or on russian citizens.
Putin is also banking that Obama will back down.
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My name is Ozymandias, King of Kings;
Look on my Works, ye Mighty, and despair!
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