This, of course, is not an entirely original thought. But I think that it is interesting to juxtapose the unique strengths Barack Obama posseses, versus the equally amazing weaknesses he must overcome.
Here's my take: Obama is obviously intelligent, erudite, and charismatic. But he is not terribly likable, and fails to connect with many average Americans.
There's a famous story about two 19th century British prime ministers, William Gladstone and Benjamin Disraeli, that I think helps illustrate Obama's weakness.
It was often said of Prime Minister Gladstone that when you had dinner with him, you came away thinking he was the the most charming man you’d ever met. Conversely, after dining with Disraeli, one came away feeling that you were the smartest, most charming person in the world.
The great politicians, such as Ronald Reagan and Bill Clinton, are like Disraeli. They make you feel better about yourself. Obama is Gladstone -- an impressive politician, but the ability to connect with average Americans is not his strength.