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But if I could pick my opponents like Socialist Skip Humphrey and (at the time) a recent GOP convert like Norm Coleman in a three way race, I think anyone could win if they worked at it, which Jessie did.

Eric, you don't want to get me started (again). Tell me exactly how Jesse "worked at it." He got tons of free media coverage as a celebrity. He hired the same ad guy Wellstone used in his first campaign (who, politics aside, is excellent). Then Humphrey tried to siphon votes from Coleman by insisting upon including Ventura in the debates. Does any other great "work" Ventura did to get elected come to mind?

When I showed up to vote in Prior Lake on election day I couldn't help but notice the unusually long lines (I voted with the before work group just before 8 AM) made up of mostly young men in the 18-15 age catagory. I recall hearing that Jessie's campaign had made an extra effort to reach young blue collar types who typically didn't go to the polls and here was evidence of it on the day that counted.
In the TV coverage I saw prior to the election and the few times I observed his rallies first-hand, I did notice a lot of 20-30 year old supporters who were obviously, a) not scrub faced young Republicans or, b)Wellstone clones from the DFL. My impression was few of Jessie's kids had ever taken part in a political event or had any previous interest in elections--and I think the Ventura campaign targeted this group, knowing that, in a three way race, an extra ten or 15 percent of the population who generally ignore election day would make the difference.
Jessie's emphasis on rock music and connection with local musicians and bands probably was conceived by the former Wellstone connection he hired (recall Wellstone's first campaign was a "youth movement"). The advertising appealed to young people, including the "thinker" ad, with a semi-nude Jessie, in the last ten days of the campaign. Also consider the election-night rock concert (I forget where--Robbinsdale Ballroom?) that went on till 3 in the morning.
After the election, the newspapers were full of stories on how many new voters showed up to vote for Jessie. This was an easy story to prove because there were so many new voter registrations the same day (since the North Star State allows same day registration). I'd say Jessie worked pretty hard to "shock the world" as he put it on election night. Going after the young vote was pretty good strategy and I don't think the elction was handed to him while he was napping.
Respectfully,