3 hours ago, ddbrown30 said:

I mean, this is kind of the whole point of the thread. He wants something I feel gives him a lot of benefit and I need to find a reasonable drawback. Since he doesn't want it to be that he's hunted, I came looking for advice.

Not every backstory has to be governed by rules, especially when you have the right group of players. I let the same player be a several hundred year old human who looked 30 in our last D&D campaign just because it was cool and was fertile ground for storytelling.

This is a player that enjoys creating and getting into characters and I want to support that.

If you are looking for a drawback that is not specifically tied to an obligation or he doesn't want to have Black Sun looking for him, say he was released peacefully from Black Sun for any one of the reasons mentioned above and is not hunted by Black Sun. However, the Hutts or some other criminal (or security) organization has discovered this and thinks he may be "convinced" to provide information on the Suns.

2 hours ago, ddbrown30 said:

I mean, this is kind of the whole point of the thread. He wants something I feel gives him a lot of benefit and I need to find a reasonable drawback. Since he doesn't want it to be that he's hunted, I came looking for advice.

Not every backstory has to be governed by rules, especially when you have the right group of players. I let the same player be a several hundred year old human who looked 30 in our last D&D campaign just because it was cool and was fertile ground for storytelling.

This is a player that enjoys creating and getting into characters and I want to support that.

I'll second (third) what @whafrog and @Lorne indicated. This is a great opportunity for obligation. As I indicated before, you can have it play out in any way you want, instead of being hunted why not just have him recognized and called out at a time of your choosing, and rather than him being hunted, it sets up a "job" he needs to pull. Either the recognizer is blackmailing him to "do this job or I'll out you", or its more of a "do this last last job and we'll let you out of the organization". Seems like a simple 5 obligation and then one mission to pay it off seems reasonable. If you or the group want to pursue it further you can, otherwise its done.

5 hours ago, ddbrown30 said:

He wants something I feel gives him a lot of benefit and I need to find a reasonable drawback...

...Not every backstory has to be governed by rules, especially when you have the right group of players.

I think that's a bit contradictory. Of course you don't need "rules" to deal with this, but even saying something like "you might have a couple contacts left in the Black Sun, but if any other criminal element finds out, it makes any interactions with them more difficult" is a bit vague, not really actionable in-game. You probably need some idea what you plan to do with it mechanically--extra setback? difficulty upgrades?--but you certainly don't have be that specific with the player.

The problem I see is what will he be doing going forward?

The best idea I've got is that as a relatively new recruit, he was involved in an operation that went wrong in all the ways that pushed his "nope" buttons - but managed to pull off the miracle that saved the operation. After the dust settles, someone with a lot authority has to publicly reward the associate who saved the day, but said associate realizes they're in over their head and really don't want this kind of life. A token reward and get cut loose with the message "don't interfere" going both directions mostly works. He won't be able to call on Black Sun contacts, because they're under orders to honor his wish to be left alone - but they won't come trying to involve him, either. If he decides to reach out and re-join they might be interested, although there will be some understandable concern about his willingness to follow through.

What if he ended up doing something Black Sun wasn't happy with, but ends up protecting him from retaliation? Maybe he fell in love with Grand Moff Tarkin's niece, and told Black Sun he wouldn't use his connection to help them. The Imperial Military would be a big enough threat that Black SUn probably wouldn't try a hit, but he isn't able to call on their resources, either. Black Sun would just leave it at "Fine. Be with her. But don't come crawling back to us. Or else."

A power play within the organization, and he backed the wrong horse. The boss he was working for was deposed, and the new guy didn't want any of the "old management's" people around. The bigger fish, however, knew that the character was a good employee and had benefited the .org many times in the past, and possibly could do so again in the future.

So the new management wants him dead, upper management wants him available for future work (hence, alive), and the goons and soldiers just do what they're told.

This means that the PC doesn't necessarily ever know exactly which faction he's dealing with any time he interacts with the Black Sun. Could be someone sent from upper management, could be someone sent from the guy that wants him eliminated, could be someone entirely neutral in the entire affair. Might create a bit of a mess if the character misread the situation and gunned down someone that was on his side....