RobinHanson comments on Why Support the Underdog? - Less Wrong
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It seems that supporting an underdog is a more impressive act - it suggests more confidence in your own abilities, and your ability to withstand retribution from the overdog. I'm not sure we do actually support the underdog more when a costly act is required, but we probably try to pretend to support the underdog when doing so is cheap, so we can look more impressive.