Barack Obama, clearly.
A charismatic if fairly inexperienced politician is elected to a Senate seat from a safe blue state, where he carves out a left-of-center record for two years.
He was also pretty lucky in that Senate race itself, seeing as how all of his opponents self-destructed.
I will never understand why the IL-GOP handpicked Alan Keyes of all people to replace Jack Ryan as their candidate.
Yeah, and that was just the general election. There's also the fact that Hull imploded in the primary.
Hull imploded because oppo research on him developed a tip that the papers ran with just a few weeks before the primary. The same thing happened to Jack Ryan after the primary. Some in the IL-GOP thought that Ryan could survive the story, but the leaders thought otherwise. Keyes was sold as someone who would run a specific type of campaign, but he chose to run one as a platform for his ideology. In any case Obama was not lucky, he had good staff that could turn up the right info on an opponent, and he used it at the most opportune time in a campaign.
Quinn OTOH was lucky.