You are, perhaps, reading too much into the word "winner" to mean "automatically succeeds" rather than "is unstoppable and bowls over obstacles that would stop most people".

Have you never met anyone with an unusually high mix of intelligence, determination, focus, and charisma (to randomly pick a few traits)? If you have, are you more likely to bet for or against them in their chosen field?

If you haven't, that is entirely possible. Such people are, by definition, rare.