Haha I was just thinking about that.
He remains mayor of Carmel-by-the Sea, not staying in only for one term.
In 1993, after Unforgiven, Eastwood decides to end his movie career, having done the best he possibly could. He runs in the Special Election to fill the 17th Congressional seat after it is vacated by Leon Panetta, who leaves to direct the OMB. He runs as an Independent and wins.
In 1999, Eastwood runs for Governor, this time as a Democrat. He either reverses the crippling energy deregulation or successfully blames it on Wilson.
In 2001, an alternate 9/11 occurs. On the list of targets was the Golden Gate Bridge. Eastwood addresses the state, and subsequently the nation, while Bush is still sitting in the elementary school in Florida, that there seems to be an organized terrorist attack on America. Eastwood is seen as "America's Governor" and as a political rival of Bush. He supports the invasion of Afghanistan but not Iraq.
Eastwood is quicker to sue the EPA in the suit that is know as Massachusetts v EPA in OTL, bolstering his standing again.
He wins on the Democratic ticket in 2004. Bob Graham seems like a really good VP choice for him, delivering Florida.
How about that?