FDR 1936 Campaign Speech: 'I Welcome Their Hatred'

He was to the manor born, but he could connect with the common man in an extraordinary way.

I read that the only politician he feared was Huey Long. Long was a charismatic person who had a platform for the masses. He was able to deliver his message with belief and hope. Whatever you think of him, he was a master politician.
If someone comes along with his personality, they will sweep the vote. Obama was in that mold, but his race was a crippling factor unfortunately. Fortunately, it wasn't too crippling. In addition, Obama does not enjoy campaigning like Long did. He gets into the fight, but he stops that mode after elections. You have to be a campaigner all the time in some way.