Longest, realistic family dynasties in democracies:

MarioLuigi

Banned
For the U.S., the longest, realistic hypothetical one I could think of was this:

Reagan/G.H.W. Bush (1981-1989)
G.H.W. Bush/Quayle (1989-1993)
Bill Clinton/Gore (1993-2001)
G.W. Bush/Cheney (2001-2009)
Obama/Hillary Clinton (2009-2017)
Hillary Clinton/Brian Schweitzer (2017-2025)
Chelsea Clinton/Tim Ryan (2025-2033)

52 years in total with Bushes and Clintons continuously either as President or as VP.
 
How about:

Reagan/G.H.W. Bush (1981-1989)
G.H.W. Bush/Quayle (1989-1993)
Bill Clinton/Gore (1993-2001)
G.W. Bush/Cheney (2001-2004)
Hillary Clinton/Russ Feingold (2004-2009)
Jeb Bush/Mitt Romney (2009-2016)
Chelsea Clinton/Tim Ryan (2017-2025)

The only impossibility there is Chelsea at the end, to young and if her mother gets blamed for the economic collapse then she has an uphill battle. But if recession has turned to depression at the end Jeb Bush second term and the last great president is Bill in the public`s mind then... Still ASB I guess.

It`s not longer in terms of years but it includes more people. If both Hillary and Jeb get two terms then...
 
Hinckley Succeeds

G.H.W. Bush/Dole (1981-1989)
Bill Clinton/Gore (1989-1996)
G.W. Bush/Cheney (1996-2005)
Hillary Clinton/Russ Feingold (2005-2013)
Jeb Bush/Mitt Romney (2013-2021)
Chelsea Clinton/Tim Ryan (2021-2029)
 
Wait... To make this be a family dynasty, wouldn't Chelsea have to marry one of Jeb Bush's sons?
 
I´m not that into American politics but what about the Kennedys? Joseph Kennedy had a pretty good start as politician when he ruined his career with appeasement and three of his sons came pretty far: JFK, Bobby who might have become president without his assasination and Ted, who without the Kopechne incident and the assasination of both his brothers might have followed them. Now it´s not terribly likely but this are four men from one family in positions of power in just two generations.
 
I modified one by Fabilius and here we go! Longest one ever, and also Chelsea is older too.

Reagan/G.H.W. Bush (1981-1989)
G.H.W. Bush/Quayle (1989-1997)
Bill Clinton/Gore (1997-2001)
G.W. Bush/Cheney (2001-2004)
Bill Clinton/Whoever (2001-2005)
G.W. Bush/Cheney (2005-2009)
Barack Obama/Hillary Clinton (2009-2017)
Hillary Clinton/Russ Feingold (2017-2025)
Jeb Bush/Mitt Romney (2025-2033)
Whoever/Chelsea Clinton (2033-2041)
Chelsea Clinton/Tim Ryan 2041-2049)

There. 68 years.
 
I think having two Presidents in a row come back from defeat is a bit ASB but then we are aiming for the maximum length of dynasty so kudos Constantinople. However what about whacking some Kennedy's in there to make it a three horse race.

Edward Kennedy/Jimmy Carter (1977-85)
G.H.W. Bush/Quayle (1985-1993)
Bill Clinton/Gore (1993-2001)
G.W. Bush/Cheney (2001-2009)
John F. Kennedy, Jr/Hillary Clinton (2009-2017)
Hillary Clinton/Whoever (2017-2021)
George P. Bush/Mitt Romney (2021-2029)
Whoever/Chelsea Clinton (2029-2033)
Chelsea Clinton/Tim Ryan (2033-2041)
 
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