I gave my player the secret that they escaped the Lottery in Easthaven and have been on the run ever since.

The party has yet to go to Easthaven, but they mentioned going there out of order during another quest and I need to be prepared now! The character's response to going to easthaven was very forceful and kind of suspicious so I now have a player hoping to kidnap them in the middle of the night and strap them to a dog sled and go towards east haven to see what the fuss is about.

I was planning on having a couple of encounters of bounty hunters coming nearby the party and engaging, but if they were to capture him or if they go to easthaven sooner and he doesn't find a disguise... how does that work?

IMO it would be fair that the town speaker would jail him until the next lottery and make a big display of torturing him before they got to sacrifice him once and for all. Obviously, the party will have to figure out how to get him free from that situation without burning bridges in Easthaven.

How would you run this? I don't know how jailing someone works or what should be in place to allow a chance of breaking out.