Your challenge is to concoct a scenario in which a political family (Roosevelt, Kennedy, Bush, etc.) has the most individuals hold the oval office. My personal best bets would be the Roosevelts or Kennedys, which is why I've posted this in post-1900, but earlier is definately allowed too!

Good luck...
 
Let Quentin Roosevelt to survive from WW1. The he serves as succesful general during WW2 in Europe. In 1952 he runs as Republican. So now you have three presidents from same family (if you count distant cousins).
 
Let Quentin Roosevelt to survive from WW1. The he serves as succesful general during WW2 in Europe. In 1952 he runs as Republican. So now you have three presidents from same family (if you count distant cousins).
I might steal this for me 1930s-40s China TL if that’s okay.
 
Have Ted Roosevelt (Theodore Jr) stay out of The Teapot Dome Scandal and get nominated as VP in 1924 and then run against Al Smith. Hoover stays involved with charitable and engineering work but does run in 1936 and has Alf Landon as vp.
 
George Bush, George W. Bush and Jeb Bush all could've gone differently had things gone right for them - Kerry beats Dubya in 2004, Jeb beats Kerry in 2008
 
George Bush, George W. Bush and Jeb Bush all could've gone differently had things gone right for them - Kerry beats Dubya in 2004, Jeb beats Kerry in 2008

If GWB is not elected to second term, would GOP be willingful to try with third looser after father and son couldn't take second term?

Perhaps better chance would has go with same as OTL but on future in 2030's or even 2040's George P. Bush (Jeb's son) winning election.
 
Have David Eisenhower get elected as a president then have one of his and Julie Nixon Eisenhower children run for president, they have 3 with 2 girls one boy that would be elegible for election because they are in their early to late 40's now. You would actually have 4 from a single family with both Ike and Nixon also.
 
Everyone needs the same surname? Will we count people from a woman’s side of the family or who marry a member of their family? If not, I am sure we can find a way to get another Harrison in the White House.
 
Not to stray into modern politics too much, but I think the possibility of a Jeb Bush presidency, despite being somewhat comical to us nowadays, isn't actually that far fetched. If the GFC had been staved off a little longer, W's legacy would probably look a bit better and Obama might've absorbed more of the blame for it. Jeb, having recently come off a governorship in Florida, still quite a swing state at the time, would look pretty good on paper in 2012. Given that Romney was able to secure the nomination, it doesn't seem beyond the realm of possibility that a moderate like Jeb could lead the ticket. None of the red states that election were close, so he can easily hold onto those. Florida was fairly close and he very likely flips it, ending up 235 electoral votes. It's a real uphill battle from there, as the next couple of blue states weren't particularly close, but it's not unthinkable. I believe he actually made a comment at one point that 2012 was year he actually should've ran.
 
Everyone needs the same surname? Will we count people from a woman’s side of the family or who marry a member of their family? If not, I am sure we can find a way to get another Harrison in the White House.
Spouses wouldn't count, they would need the same blood - so a grandson born to a presidents daughter would count, even without the surname
 
Not to stray into modern politics too much, but I think the possibility of a Jeb Bush presidency, despite being somewhat comical to us nowadays, isn't actually that far fetched. If the GFC had been staved off a little longer, W's legacy would probably look a bit better and Obama might've absorbed more of the blame for it. Jeb, having recently come off a governorship in Florida, still quite a swing state at the time, would look pretty good on paper in 2012. Given that Romney was able to secure the nomination, it doesn't seem beyond the realm of possibility that a moderate like Jeb could lead the ticket. None of the red states that election were close, so he can easily hold onto those. Florida was fairly close and he very likely flips it, ending up 235 electoral votes. It's a real uphill battle from there, as the next couple of blue states weren't particularly close, but it's not unthinkable. I believe he actually made a comment at one point that 2012 was year he actually should've ran.
I have always thought that myself, actually. Even if Jeb get's elected, I doubt he'd a second term - I could see him being a Republican Jimmy Carter, quite inoffensive but in such a way that hurts his chances at reelection
 
If Washington hadn't likely been sterile I could see a bunch of his descendants getting elected throughout the 1800s on name value alone.

And another possibility could be Lincoln family. Abraham Lincoln avoids his assassination and serves two terms. Later Robert Todd Lincoln might be encouraged to serve as president too and is elected perhaps in 1900 or 1904. RTL's son Abraham Lincoln II (or might has some different name but that not matter) becomes too president at some point.

And even better if all Abraham Lincoln's sons would survive to adulthood.
 
This is probably ASB, but have Roosevelt not run for a third term in 1940 and Joe Kennedy Sr. picked instead. JPK or JFK could run in 1960, be assassinated, and open the door for Bobby in ‘68 or ‘72. Further down the line, around the year 2000, have one of the Kennedy children or even Teddy win against a Republican incumbent.
 
Have David Eisenhower get elected as a president then have one of his and Julie Nixon Eisenhower children run for president, they have 3 with 2 girls one boy that would be elegible for election because they are in their early to late 40's now. You would actually have 4 from a single family with both Ike and Nixon also.
ISTR reading that David's college professors thought he was very smart, to the point of saying to each other "When David is President...", i.e. "when", not "if". So not so far-fetched.
 
There's not exactly a shortage of political Kennedys - though not all of them are equally competent.

duh-duh duuh duh *finger snap* *finger snap* :p
 
Well what do you now. Abraham Lincoln’s maternal grandmother was a Harrison, plus he managed to get a Harrison relative acquitted of murder. Though apparently he wrote that he was descended from a Virginian family with no distinction. Makes sense with his family being from a different branch and how the firs Harrison only lived a month in office, with the second Harrison only begging president seven administrations after Lincoln’s own.

So yah, distant relatives. The Roosevelts get away with it due to living in the same city and FDR marrying Eleanor, a favorite niece of Theodore. We might want to consider having a thread on city and state political families and how to expand them. The Lees would do well, if only because of numbers and managing to marry into the Curtis family.
 
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