the man in the high castle obviously sucks ass but a concept i think you could carry on is a weaker depression recovery leads to a loss in the cold war. perhaps al smith is elected over fdr and has smaller majorities due to catholicism, fails to recover much, and the US goes into WWII sort of already bruised. we still win of course, but the economy goes into recession (like many were expecting after WWII) and the soviets start gobbling up countries while the US keeps electing old righters until it inevitably collapses and gets replaced with a democratic socialist hybrid regime.
1933-1941: Al Smith (Democratic)
1932 def. (with Huey Long) Herbert Hoover (Republican), Norman Thomas (Socialist)
1936 def. (with Huey Long) Herbert Hoover (Republican), John Brinkley (People’s)
1941-1949: Roland Morris (Democratic)
1940 def. (with Carl Bailey) Thomas Dewey (Republican), Charles Lindbergh (America First)
1944 def. (with Carl Bailey) Joseph Bottum (Republican)
1949-1957: Howard Buffett (Republican)
1948 def. (with Everett Dirksen) Robert Moses (Democratic), Wayne Morse (Liberal)
1952 def. (with Everett Dirksen) Carl Bailey (Democratic), Harold Stassen (Liberal)
1957-1961: Norton Simon (Center)
1956 def. [backed by Northern “Free” Democratic-Liberal Pact] (with Brien McMahon) Thomas Werdel (Republican), Carmine DeSapio (Democratic), Vito Marcantonio (Radical)
1961-1969: Merritt B. Curtis (Republican)
1960 def. (with Ellis Berry) Norton Simon (Center), Earl Long (Democratic), Walter Reuther (Radical)
1964 def. (with Ellis Berry) Nelson Rockefeller (Center), Orval Faubus (Democratic), Gore Vidal (Radical)
1969-1969: Mark Hatfield (Center)
1968 def. [disputed] (with Michael Harrington leading “Blood Orange” coalition) Ellis Berry (Republican), Lester Maddox (Democratic), Quinten Burdick (Independent [Agrarian])
1969-1969: Edwin Walker (Military)
1969-1969: Scott Camil (Military leading Free Officers Movement)
1969-1975: Scott Camil (Free People’s)
1975-1987: Robert Zimmerman (Free People’s)
1975 def. Jesse Owens (Free Enterprise), Quinten Burdick (Agrarian), Bob Avakian (Occupying Officers), Hubert Humphrey (Miners)
1981 def. Bob Avakian (Occupying Officers), Buckshot Hoffner (Agrarian)
1987-1999: John Kerry (Occupy)
1987 def. Tom Hayden (Free People’s), George McGovern (Agrarian), Ron Dellums (League)
1993 def. Angela Davis (Free People’s-League), Hunter S. Thompson (Freak Power)