His example was kind of confusing, since you'd want the money, but not to get shot. So it's kind of reversed.

So take his example, but imagine it's a bad outcome. Perhaps you have to pay the amount of money under the cup. The majority (98 red cups) have more overall money penalties, but spread out among more cups. A tiny minority (2 green cups) have less overall penalties, but it's a lot more concentrated. Assuming you averaged everything out, picking a green minority cup you'd have to pay $50, picking a red majority cup you'd have to pay $2...despite the red majority having twice as much penalties overall.

His example was kind of confusing, since you'd want the money, but not to get shot. So it's kind of reversed.

So take his example, but imagine it's a bad outcome. Perhaps you have to pay the amount of money under the cup. The majority (98 red cups) have more overall money penalties, but spread out among more cups. A tiny minority (2 green cups) have less overall penalties, but it's a lot more concentrated. Assuming you averaged everything out, picking a green minority cup you'd have to pay $50, picking a red majority cup you'd have to pay $2...despite the red majority having* twice as much penalties overall*.