Alright, here goes:
The POD is 1954. Franklin D. Roosevelt Jr., a Representative from New York, wins the gubernatorial nomination as he intended. Roosevelt then defeats the Republican nominee.
Governor Roosevelt has a popular record as Governor, and he impresses Senator John F. Kennedy in 1958, when he narrowly defeats Republican Nelson Rockefeller. Roosevelt runs for President in 1960, and wins the Democratic nomination. He defeats JFK, LBJ, and all the others for the nomination, and he selects Sen. Kennedy as his running mate. (Roosevelt/Kennedy: One of the awesomest tickets evar

)
President Roosevelt serves from 1961 to 1969, and he's pretty successful. He's succeeded by Richard Nixon, who still gets involved in Watergate and is succeeded by Gerald Ford in '74. President Ford gets primaried by Ronald Reagan in '76, and Reagan wins the general election. Reagan is a popular President from 1977 to 1985, and he wins re-election by a near-unanimous landslide in 1980.
The third President Roosevelt highly inspires his cousin, Theodore Roosevelt IV. Since TTL's GOP is more conservative, Roosevelt joins the Democratic Party, although he's more of a moderate Democrat. Roosevelt runs for Governor of New York in 1978, and wins the election. He is re-elected overwhelmingly in 1982, and despite much speculation, he declines to run for President in 1984 (he recognizes a suicide run when he sees one). He is re-elected to a third term in 1986, but again declines to run for POTUS in 1988 - again, he feels that he cannot defeat George Bush. But when 1992 comes around, and Theodore Roosevelt is serving his fourth term as Governor of New York, he feels confident enough that he can win. So he runs for the Democratic presidential nomination, and he wins an uber-victory - he's a centrist with both business credentials, has a huge record as Governor, there is no Mario Cuomo to challenge him, he isn't disliked by liberals like Clinton was, and, of course, he's a Roosevelt, and therefore has lots of name recognition and is RICH.
Therefore, Governor Roosevelt wins the nomination overwhelmingly (I doubt Clinton would even run). He selects Arkansas Governor Bill Clinton as his running mate, since Clinton is a charismatic small-state Governor who is in ideological tune with Roosevelt. And so the Roosevelt/Clinton ticket defeats Bush/Quayle overwhelmingly in November. I'm not sure if Perot would run.
So there you have it. Roosevelt/Kennedy in 1960, and Roosevelt/Clinton in 1992, all in the same timeline.
