Finis G. Valorum was probably the biggest loser in the entire Star Wars Universe. At one point in time, he was the Supreme Chancellor of the entire Galactic Republic, so he was obviously a smart guy and knew how to play his cards right. He even survived an assassination attempt by John Wilkes Bith. However, shortly after becoming Chancellor, he was booted out because nobody in the Senate liked him, and, as a matter of fact, they threw in a "Vote of No Confidence", which pretty much means the Senate thinks you are really crappy.