Happily, it won't be hard.
David Palmer (24): A trusting man easily manipulated by those close to him and apparently consumed with fear over public riots, his accomplishments include authorizing an illegal raid into xYugoslavia that later triggered a wave of kidnappings, murders and attempted assassinations during primary season. This would turn out to be the high point of his career, since he was later temporarily deposed by his own cabinet and the incompetence of his trusted intelligence agencies led to the the hostile detonation of a nuclear device on American soil. Sorry, make that the first hostile detonation of a nuclear device on American soil. It wasn't the last.
Inexplicably, despite Palmer's many catastrophic decisions the US would later elect his brother - then notable for an extra-marital affair that ended with blackmail, two or three murders, a kidnapping and a suicide - as President.
Can Obama outperform David Palmer? Yes, because even George W. Bush outperformed David Palmer.
Tom Beck (Deep Impact: An inspiring orator and apparently competent administrator, he had the monumental bad luck to be President in the run up to what could have been an Extinction Level Event for the world. Although America took part in (and probably paid for most of) an international effort to destroy the asteroid responsible, these efforts were only partially successful and much of the Eastern seaboard was lost.
The creation of Arks filled with the best and the brightest probably annoyed all those people who failed to make the cut, many of whom would have survived to the next election.
Can Obama outperform Beck? Statistically, natural ELEs are a fairly atypical event in US politics and I expect this particular challenge will not come up. It's not hard to be luckier than Beck.
Douglass Dilman (The Man): Although President, he was not elected to the position but rather was rose to the position after a freak accident killed the previous President and two of his successors.
Can Obama outperform Diman? Yes, because unlike Dilman, we know Obama is capable of winning an election and earning the legitimacy that comes with winning an election.
- Obama will have to do better than these black Presidents