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George Herbert Walker Bush

Raised in Greenwich, Connecticut

Lieutenant JG, US Navy (1942-1945) and awarded Distinguished Flying Cross

Star first baseman for the Yale University baseball team and member of Skull and Bones & Phi Beta Kappa

Self-made millionaire in the Texas oil industry

Son of US Senator Prescott Bush (1953-1963)

Congressman from Houston (1967-1971)

Ambassador to the UN

Chairman of the RNC

Envoy to China

Director of the CIA

Vice President of the US (1981-1989)

President of the US (1989-1993)

Bush was able to appeal to the working class folks by stressing his political career in Texas, and his love of country music and pork rinds.

Despite presenting himself as a southerner, Bush was never able to fully escape his New England roots, e.g. summer vacation home in Kennebunkport, Maine.

His biography in Wikipedia states that he got his start in the oil business after graduating from Yale with the help of his father who was on the board of Brown Brothers Harriman. To do this, he moved his growing family to Texas where the Republican party at that time was barely in existence.

Suppose Bush decided not to move to Texas and follow his dad in the investment banking business. While Barbara raises the kids in Greenwich, George commutes to his job in Manhattan and is the family's breadwinner.

After his dad retires from politics in 1962, I can envision George entering politics in Connecticut and establish himself as a pro-business, socially liberal politician (Note: when Prescott first ran for the Senate in 1950, he was criticized for his ties to Planned Parenthood which hurt him among Catholics) instead of a Reagan-style conservative.

In this scenario, he probably would not become President of the US. Jeb and George W. would probably follow their dad's moderate politics if they decided to run for office. They would probably move to New York or Massachusetts.

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