The biggest problem in Obama's world, and with many others on the Left, is that Obama wanted to be friends with Putin. When Obama whispered in Putin's ear and told him, 'I know you may not like me now sweetheart, but I will be more flexible for you later, darling.' he meant it. He was begging Putin to give him a chance to be 'friends'.
Obama was raised and trained that the Soviet Communist system was the 'ideal' and he wanted to ally himself with it. He did not intend to make America an ally of Russia, but he did intend to make himself a friend of Russia. However, Putin has no respect and no use for Obama. And that hurt Obama deeply.
If Putin was a politician in America, he would be labeled a fanatic "right wing extremeist". This has thrown Obama and the Left for a loop. The American Left's verision of a 'Leftist' is a sweater wearing, latte sipping, homosexual vegan, who is elite, rich, and self-sanctified. To have Putin, who's position is the very definition of a 1960's verison of Leftism or Communism, come out as a homo hating, shirtless macho man White guy, who shoots bears on the weekend for fun, has thrown them all into a tizzy. They don't know what to do now. Their version of Leftism is weakness, Putin's version is strength.
The American Left now views their once hero as a neanderthal, and Putin views them as weak, stupid, bleep, and never the twains shall meet. This elitist, intellectual, feckless, 'tolerant', version of what the American Left calls 'Leftism' always gets crushed by reality anytime it is rolled out on the world stage.