It's a tough thing. If you vote for someone with no ties to Washington, you are "voting for someone with no experience." If you vote for someone entrenched in DC, you are "voting for a career politician." It's a lose/lose proposition haha
Obama came from Chicago politics. He was "new to DC" like John Carmack is "new to Occulus Rift". He might be working with a different crew now, but he's bringing a lot of "experience" to bear.
When he was elected to the Senate, he was new to DC. When he was elected to the Presidency as a sitting US Senator, not so much.