I’m confused. The other players are also part of this event or are not?
What people are trying to express here, is the concept that your event becomes flat and dull if the focus is overly on getting to the end.
Your question is bothersome for its lack of details. Since we have no clue as to the importance of this event to the character, we’re left only to guess as to which parts of the scenario can and should be played with.
This is only a no win situation if you insist it be so. Presumably this has to be a negative event to the player (generally why such an event would be included). But the entirety of the event does not have to consist of only negative events.
- Did they go to jail? Maybe he made useful contacts among the underworld/thieves guild or other allies.
- Did they uncover some deeper plot that will affect future events?
- Did they have a drug habit and this allowed them to ‘get clean’?
- Did they take the rap for someone else, who owes them a big favor?
These are the types of things you can consider.
If you do go to trial, consider that trials don’t have to be based on the US model. If you want to make it interesting, make it a bit unfamiliar to the players. If they’re expecting a judge, jury, prosecutor, and court appointed lawyer, they should be in for a rude shock.
What I would do, tribunal. Tribunals are more fun. Multiple judges, which don’t even have to be judges. They can be political appointees, military, council of elders, and on and on.
- Imagine the half-wit in-law of the local Baron holding lives in their hands.
- Imagine two of the judges hate each other so much that they always vote opposite to each other.
- Can other party members influence these multiple judges (can they try to bribe the judges, do tasks to gain their favor?).
If the character hasn’t been played yet, then this doesn’t have to be a lose/lose situation. Maybe the actual lose is ‘if you blow this’ life imprisonment and roll up a new character. Maybe the win is less jail time (not saying this is enough, but along with other risks/rewards it might be something to consider).
Winning is defined differently to different people. For some a good story is enough. For others an objective gain is required. If you can rethink win as the endpoint, and convert the scenario to a series of wins and losses (perhaps even simply making it count on how well the situation is dealt with), then the scenario automatically has more depth from a game theory standpoint.