Sinnerman

Sinnerman is a side job in.

Walkthrough
Sometime after Life During Wartime, Wakako Okada will contact you with a rather unique job: the one hiring you wants to also be there when you do the job to make sure it's done.

Head to the location to meet with the man, Bill Jablonksy, who reveals the target is Joshua Stephenson. Get in the car and talk to him where you can learn the man murdered Bill's wife and somehow managed to escape death row as someone high up managed to bail him out of jail. As you might have guessed, Bill didn't really think this whole plan through well and there will be others with Joshua.

The police car you're after will then pass and you'll need to give chase for awhile before it stops near a blockade and Bill will demand you stop the car. However, he's so set on Joshua dying, he'll get out of the vehicle and try to take on the police officer protecting Joshua. Officer Vsaquez will order Bill to stop and to not get close, but Bill will ignore this. If you don't intervene here, Vasquez will kill Bill once he's too close and Joshua can be heard crying out to stop shooting. If you do intervene, you can then help Bill take his revenge, but will lose access to the other side quests that open up with Joshua.

If you didn't stop Vasquez from killing Bill, an odd turn of events will play out where Joshua, Vasquez, and a woman named Rachel will argue that they need to get out of there and Joshua invites you to come with them. You can talk to him for a bit but eventually the group gets back into the police vehicle, and you can choose to go along or not. If you don't go along, the quest will end here and you won't be able to do Joshua's quests.

If you want to go along, get in the vehicle where you can talk more with Joshua to learn while he was in jail, he got into Christianity and realized all the harm he committed in the past and wants you to tag along for the day to talk to as his other companions aren't really helpful for that. He'll make sure Wakako and you are paid what Bill had originally put up for the contract if you accept this. At this point you can still choose to leave by asking for them to stop the vehicle, or agree to stay with him for the day. If you accept to stay, the quest will then conclude on arriving at Gloria's and start the next portion, There Is A Light That Never Goes Out.

Journal Entry

 * You're right about one thing - this job from Wakako stinks to high heaven. Besides, you're above doing plain ol' hit jobs. Probably no harm in talking to Bill Jablonsky and seeing what his deal is. But if I were you? I'd take a hard pass.

Objectives

 * Talk to Wakako Okada.
 * Sit and wait for Bill Jablonksy.
 * Talk to Bill Jablonksy.
 * Follow the car.
 * Stop the car.
 * Exit car.
 * Follow Bill Jablonsky.
 * If Bill is killed and you go along for the ride:
 * Talk to Joshua Stephenson.
 * Get in the NCPD vehicle.

Bugs

 * Sometimes when Wakako calls you about this job, the audio and subtitles won't appear when she explains what the job actually entails.