Rooting for the underdog, the Cinderella story, the little guy gives us hope. It gives us that bit of hope that the system is not flawed and scaled so heavily in favor of people with all the perks in life.
When we see an underdog story, we watch it, we get wrapped up in it. And for a brief moment we know that anything is possible.
Unfortunately, those are really rare stories.
Rarely does the little guy win, even if the little guy has more talent and skill. Sad really.