Was there ever an instance where the loser of a Presidential election died during what would have been their term of office, second term included? If so who was his VP?
Wendell Willkie ran in 1940 and died in 1944. Interestingly, his running mate (Charles McNary) died eight months earlier. So, we don’t know the answer to that question in that instance.
Horace Greeley died between the election and inauguration. It would have been interesting how things would have played out if he had won: the Electoral College wouldn’t have met, so the election could have gone to anyone.
His running mate, B. Gratz Brown didn’t even get most of Greely’s electoral votes.
To clarify why we don’t know, under the Presidential Succession Act of 1886 Willkie’s Secretary of State (whoever that would be) would act as President.
Looking through Wikipedia’s list of unsuccessful candidates gives us three more beyond Wendell Wilkie (mentioned above):
[ul][li]Hugh White ran for president in 1836 and died in April 1840. But his running mate was John Tyler, who eventually got to be president anyway.[/li][li]Stephen Douglas ran in 1860, but he was done in by debating Lincoln too hard, dying in 1861. His running mate was the excellently named Herschel Vespasian Johnson.[/li][*]Horace Greeley ran in 1872, lost, and didn’t even make it until the Electoral College convened, dying in late November of that same year. His running mate was Benjamin Gratz Brown, who actually got some votes for president in the Electoral College because of this. (Edit: Though, as RealityChuck points out above, not all of Greeley’s votes, which had to sting a little.)[/ul]
This would have been an interesting case. As I’m sure many people are aware, the Democratic Party, which had been the dominant party in the years leading up to the Civil War, split in the 1860 election over sectional issues. The northern half of the party nominated Douglas and the southern half nominated John Breckinridge (who was the incumbent Vice President). Both candidates made some attempt to appeal outside of their section by nominating a running mate from the other section; Douglas chose Johnson from Georgia and Breckinridge chose Joseph Lane from Oregon.
Of course, both men lost and Lincoln and the Republicans won. But suppose there had been slightly more success in attempts to unite the Democratic Party and Douglas was able to win as the sole Democratic nominee. He would have had Johnson (or maybe Breckinridge) as his Vice President.
Southern radicals had publicly stated they opposed Douglas almost as much as Lincoln and planned on seceding if Douglas won. So Douglas would have faced the same secession crisis Lincoln faced.
And then Douglas would have died in the third month of his Presidency (I’m assuming he died on the same date as he historically did). At that point, the Confederacy already existed and the war had begun. The United States would have suddenly had a southern President leading the country in a war against the seceded southern states.
Another man who came very close to being President was Garret Hobart. Hobart was a New Jersey politician who was William McKinley’s running mate in 1896. They won and Hobart became Vice President.
Hobart was well-liked and effective and it’s almost certain that he would have run again alongside McKinley in 1900. But he died on a heart attack in 1899. So Theodore Roosevelt was chosen to run as McKinley’s VP candidate in 1900.
So it was Roosevelt rather than Hobart who became President when McKinley was assassinated in 1901. Hobart would have only been sixty in 1904 and most likely would have run for a second term. So Roosevelt wouldn’t have had a chance at the Presidency until at least 1908.