Despite winning all season, your baseball team can disappoint in the playoffs. The Oakland Athletics played 162 games and won 60% of them, then lose the 1 game wildcard playoff (again!). All probable outcomes suffer from statistical significance. If you are 60% sure your trade will be a success, that is a phenomenal edge. However, if you make a single bet, then 4 times out of 10, you will lose. And remember, you only care about the outcome realized, like the Athletics going home, all that matters is what happened. Life has a statistical sample size of 1.
Then, how do you capitalize on your edge? Make more bets, play more games. In a 7 game series, the Athletics win 7 times out of 10. If you place 41 trades, then 90% of the time you make moe money than lose 90%.