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An idea that I had was, Former Governor of New York Mario Cuomo making a comeback in the 2000s. In this scenario, Bill Clinton nominates Cuomo to serve as United States Ambassador to Italy, and Cuomo serves in that position from 1995-1997 (I was thinking this would help his foreign policy credentials). Cuomo runs for Governor of New York in the New York Gubernatorial Elections of 1998 and 2002, and wins the rematch against George Pataki. Sometime in early 2003, Cuomo announces his candidacy for President of the United States. Could Cuomo win the nomination in this scenario? I think him serving as Governor between 1999-2003 would give him a 9/11 boost. If he wins the nomination, can he defeat George W. Bush? For a VP nominee, I was thinking he'd pick either Dick Gephardt or Bob Graham. If Cuomo wins in 2004, can he defeat John McCain in 2008?

Another option could be Daniel Patrick Moynihan retiring in 1994, and Cuomo running for US Senate instead of re-election as Governor. Or, Cuomo defeating Al D'Amato in 1998.
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