The computer just ate my response so I'm going all over again:
LH: Did you ever see the Monty Python episode with "Dennis Moore" the highwayman who robbed from the rich to give to the poor, after some time the once rich were destitute and the erstwhile poor were now fat, happy, ungrateful and demanding. He ended up stopping coaches and re-distributing the property among the passengers.
Some famous underdogs through history:
Confederate States of America
Japanese Empire versus Gt. Britain and USA
Chinese warlords versus Japanese Empire
Pakistan versus India
India versus China
In the game of GO, it may take an expert to tell who the underdog is.
The last Star Wars episode I went to, I rooted for the Empire because I knew they were the true underdog: the scriptwriter was agin' 'em!