Hi! Being from Chicago with friend's and relatives in all parts of government, I can give you my insight.
After law school (I hate Harvard) Mr. Obama chose to become a community advisor and practice some law. He had already chosen his ultimate goal. This man is extremely narcissistic and began following the writings of Saul Alinsky.
He lived in Hyde Park, a very integrated section of Chicago. He became involved with member's of "The Weather Underground," where he was further taught their way of doing things.
Enter Emil Jones, the head of the Illinois State Senate. He was Obama's mentor and taught him Chicago style politics. Obama runs and wins a seat in the Illinois Senate. He was actually losing, but the incumbant got caught up in a scandal.
Obama runs for Congress and loses by a margin of 2-1 to incumbant Bobby Rush (former Black Panther). Obama returns to Illinois Senate.
Obama gets re-elected to the Illinois Senate. His voting record is nothing to brag about and he barely writes a bill. Approximately 127 times he votes present.
Obama runs for the Illinois Senate with heavy backing from Senator Dick Durban and the head of the Illinois Senate. The race was close with his Republican advisary, when Obama's opponent got wrapped up in a sex scandal. The Republican's (for some reason) brought in Alan Keys from Maryland (also African-American) to run against Obama. Most Republlican's did not vote in that race. Talk about Obama's opponent's having luck.
Obama becomes a US Senator. When Senator Kylwas asked how much he knew about Obama, he replied; He came to the Senate and didn't seem to care about making friend's. He barely wrote any legislation but he was running for President the day he arrived.
Obama runs for President. David Axelrod runs his campaign and pulls the wool over the eyes of most American's. People had no idea of what he stood for but voted for him.
I hope that helps.