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I’m one of the minority who rarely root for the underdog. One reason is what prospect theory/behavioral econ suggests about utility functions: the amount of pain felt is a function of the difference between outcomes and expectations, and the pain of failing to meet expectations is generally much greater than the joy of exceeding them. But another reason is that I find it entertaining and inspiring to witness greatness over a long timespan, and upsets diminish our perception of greatness. I’d much rather marvel at consistently superhuman performances by Roger Federer and LeBron than watch a sport where there’s so much parity that there are no transcendent players.

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Fascinating and great point re: expectations. There is another line of thought I didn't quite get to here that the stakes are generally so much lower for underdogs and their failures for that reason are a bit less publicized. So survivorship bias shows us underdogs persevere when in reality a lot of underdogs fail and we just don't acknowledge it.

Also really great point about greatness over a long timespan. I do think we tend to see the psychology of top dog appreciation play out in a lot of retrospective looks (i.e. eulogies) but I also wonder if there is another layer on the top dogs who embrace their villain role. I.e. Elon Musk vs. a Satya Nadella or Warren Buffett.

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