Well, the sports analogy was my own interpretation of what he said.

Game theory question time: you and N other players are playing a dice rolling game. Each player has the choice of rolling a single twenty-sided die, or rolling five four-sided dice. The player with the highest total wins. (Ties are broken by eliminating all non-tying players and then playing again.) Now, rolling 5d4 has an expected score of 12.5 and rolling 1d20 has an expected score of 10.5, so when N=2, it's obviously better to roll 5d4. However, when N becomes sufficiently large, someone is going to roll a 20, so it's better to pick the 20-sided die, which gives you a 1 in 20 chance of rolling a 20 instead of a 1 in 1024 chance of getting five 4s. For exactly what value of N does it become better?

Edit: Fixed stupid math mistakes. That'll teach me to post after staying up all night!