Obama accomplished one of his primary goals: establishing an American national health insurance that is too popular to abolish. Johnson was successful in radically changing the role of government in social programs, which was what he wanted to do. Roosevelt convinced the American people to reject both Communism and Fascism, which many if not most Americans in 1932 were likely futures, and then managed to get the United States into World War II even though most Americans were isolationists (without Roosevelt, there is a good chance American would not be western style democracy, and that the thrid Reich would now be approaching its 100th anniversay). Carter and Hoover failed in all their policies, but both were seen as nice guys. Its too early to tell with Trump though he has managed to put a brake on the leftward shifing of the judiciary which was one on his major goals.
For super-losers, I would suggest Andrew Johnson and William Henry Harrison.