George started cheerleading in high school at Andover. As Andover was an all male school, you can forget the theory that he did it to hang out with the female cheerleaders. This story (link taken from the "where did George go to High School" thread) suggests he did it because he enjoyed entertaining a crowd.
http://www.nytimes.com/library/politics/camp/061000wh-bush.htmlIt doesn't suggest his being a jock hanger-on had anything to do with it. But I would guess it did. We didn't have male cheerleaders where I went to high school, but when the girl's basketball team went up against the #1 team in the state, the boy's team got some cheerleader type outfits and did an excellent job of rallying the school around our gals (who lost in the final seconds). I can see where Georgie might have wanted to do the same for his jock friends.
Which I suppose makes him an excellent athletic supporter.
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