I think sincerity is a complete explanation, c.f. Charles Platt's Cryoptimism posts on Alcor's finances: 1, 2: "First, I find it ethically unacceptable that provident people should subsidize improvident people." Note that, in your posited scenario, he would be one of the suckers, not one of the rich guys. So that suggests as a possible cause libertarians in a group not understanding when you do actually need to make things work that way.
Today's post, You Only Live Twice was originally published on 12 December 2008. A summary (taken from the LW wiki):
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