The loser must beat a notoriously difficult video game, Dark Souls, Elden Ring, whatever their personal nemesis is, before next season's draft, with progress checked in the group chat. Hundreds of hours of dying to the same boss. Tailor the title to whatever game the loser has publicly failed at.
The long haul: this is not a one-afternoon sentence. With a time commitment of several months, 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.