Presidential Loser #1: John Hancock 1788
Technically, the first election for the President of the United States wasn’t much of an election because George Washington ran unopposed, but John Hancock had already lost years before in 1775 when the Continental Congress selected the Commander in Chief for the Continental Army. People must’ve pretty much figured whoever led the army, assuming he didn't get himself killed, would someday probably also lead the country. Hancock, who was already President of the Congress, assumed he would get the nomination. John Adams records in his diary that Hancock had a big smirk on his face when Adams rose to give the nomination. Hancock and the Adams boys were tighter than a button-down shirt on a body builder, or at least they were up to that time. Adams gave his speech, building up with glowing praise their nascent country’s leader and when he got to the name, “George Washington,” Hancock looked like he’d just found a dead cat in his lap. Ever after that, Hancock’s star was pretty much on the decline. He did do the thing with the fancy signature, on July 4, 1776 when he said in front of the other delegates, “King George will be able to read this without his spectacles.” Except he never said that. He did sign on July 4, but that was just on the copy they sent off to the printers. He didn’t get around to putting on his fancy signature until August.
In 1788 not hoping to be president, Hancock allowed his name to be put forth for Vice President. He got a measly four electoral votes, none of them even from his own state of Massachusetts. Those had gone to John Adams, the man who’d done him dirty back in ’75.
The Result
George Washington: 69
John Hancock: 4