Weekly for a month, the loser tapes dollar bills to vending machines with notes reading 'From the worst fantasy manager in [city], have a snack on me.' Strangers get snacks; the loser gets a paper trail of shame. Photo documentation feeds the group chat.
The long haul: this is not a one-afternoon sentence. With a time commitment of one month, the punishment keeps paying out (for everyone else) long after the season ends. Long sentences need a written end date and a league-appointed enforcer who checks compliance.
Seen in the wild: fantasypunishments.com