That's a good question. Oh right, when it comes to the voter fraud issue, he lost the majority vote twice. Lost the DOJ investigation, over 50 court battles, the supreme court, the electoral college, the senate, the house of representatives.
Politically, he's the first president to have all of the following:
Lost the majority vote in both of his elections.
Is impeached (Might be twice now)
Lost the Presidency as Incumbent
Lost the House - flipped to blue
Lost the Senate - flipped to blue
Lost the White House - flipped to blue.
Blue waves motherf**ker :D
I think he might be the biggest loser in Presidential History. At least he never does anything half-assed. Oh wait, running the country in the last year of his presidency. That was something you'd expect of a office temp with a bad attitude.