“Everyone likes an underdog.”

“I don’t.”

New York is a pretty special place. And New Yorkers are special people. They’re the only people in the world who will root passionately for a team that has won one out of every four World Series, a team that spends more money than pretty much every teams combined, a team that is always the favorite to win. From 1996 to 2000, when the Yankees won four out of five championships, it was an orgy of winning. And for New York, it wasn’t enough.

Poor Boston doesn’t know what to do with itself since the Red Sox started winning. For 80-odd years, the Red Sox were the underdog. Bostonians thrived on their underdog status. They blamed Steinbrenner, they blamed inequity, they blamed everyone but themselves for their problems.

Everyone knows what happened next. A hedge fund winner bought the team and hired some numbers guys and revolutionized the game, winning three World Series in the process.

Now, nobody in Boston cares. They are unaccustomed to rooting for the favorite.

Boston raised underdog-ism to an art form, but as you travel around the world, it is the love of the underdog that prevails. Ever been to a pro tennis match? The crowd typically goes with whoever is losing. Look at the UConn women’s basketball team. They are so dominant that they have generated a huge backlash.

And outside of sports, we’re always rooting for “the little guy,” “Main Street,” the disenfranchised, the underprivileged.

It takes a different breed of cat to show up and root for the Yankees to win their 28th World Series, or to root for the UConn women when they are up 65-12 and pouring it on.

It’s no accident that both the Yankees and Wall Street are in New York. In the markets, you want to bet on the favorite, the winners. You don’t want to bet on the underdog.

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