Initially, rather than designating Presidents as insiders and outsiders, I was going to designate them as Senators and Governors. However, several Presidents, including George H.W. Bush, would not have fit into these categories.
No, George H.W. Bush was never a U.S. Senator, but he was much more of a Washington insider than Barack Obama, or even Dick Cheney. In fact, when George H.W. Bush ran for President in 1988 - and in 1980 - the one thing that everyone could agree on was that he had a long resume, even if he couldn't seem to hold a job for very long.
For the record, Bush had held elected office in Washington at one time, having served as a U.S. Congressman in the 1960s. From there he held several posts in Washington (with a brief exodus to Beijing), ranging from the highly political Republican National Committee chair to the highly unpolitical head of the CIA (a job that kept him off of Ford's 1976 ticket).
Did this experience help him? Perhaps. In my view, Bush's greatest personal success was the liberation of Kuwait, achieved by forging a broad coalition with agreed-upon objectives - objectives which were accomplished. I don't know if "no new taxes" truly qualifies as a blunder, but I'm sure that some disagree with me.
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