Clint Eastwood
Famous Actor, Director, Producer
Mayor Carmel-by-the-Sea - 1986-1988
Governor of California - 1991-1999
President of the United States - 2001-2009
1990 Gubernatorial Election - 50% Eastwood, 44% Feinstine
1994 Gubernatorial Election - 55% Eastwood, 39% Garamendi
2000 Presidential Election - 51% Eastwood/Engler, 45% Gore/Lieberman
2004 Presidential Election - 56% Eastwood/Engler, 41% Dean/Clark
John Engler
Businessman
Governor of Michigan, 1991-2000
Vice President of the United States, 2001-2009
Rumored Presidential Candidate, 2008, declined
Presidential Candidate, 2012 (Dropped out after a poor performance in New Hampshire)
The best timeline.