The group as a whole has bad luck, or his character does if he is alone.
- Steps on twigs when trying to sneak.
- Road construction gang closes the bridge he was going to cross over.
- He gets the sour mug of ale from the waitress' tray.
- Enemies picking targets "randomly" team up on him, not anybody else.
- His treasure chest is the one with the least cash in it.
- His treasure chests have cool magic items in them … for the other PCs to use.
- Tax collector wants you yes you to pay the toll for everybody in the group.
- There is no room at the inn if you ask, but there is when somebody else asks.
- Receives a crit every session (which may be min damage if it really matters).
- Gets the 'NPC has no useful information' result on the chart.
Do only one of these per day / session at first, later on the bad luck gets more frequent ("stronger").
If the PC is a Halfling, per Mordenkainen, he may receive a message from a halfling priest. Something about you is not in its natural state, and you need to talk to the gods about it.