Even the Cowboys (the most expensive franchise in the world) can’t seem to buy a win these days—and that’s saying something.

"No sports fan is one-dimensional, but editorial media and league distribution deals have increasingly forced fans into one, simple box," said Harit Pathak, co-founder of EssentiallySports.

In a departure from her family's sports-oriented legacy, Taahirah O'Neal, the eldest daughter of basketball legend Shaquille ...