A/N: I have two headcanons for the jailer's personality. The first is that he's a calculating, sadistic freak. The second is that he's a tactical, almost merciful average guy. I decided to write about the second one cause why not?
Warnings: Death, possible implications of suicide and abuse, poor jailer just wants to do his job without worry, town possibly loses, and language.
Disclaimer: I still don't own TOS.
Other: This is probably the last thing I'll publish because my senior year is coming up and I'm going to very busy.


The jailer paced around his room, wondering who he should question next. It's been a few days since the mafia or the serial killer attacked. According the medium, the dead really haven't been helping. Then again, the woman could be lying about being the medium and was just trying to survive, making up a story about how she was framed. He finally decided on questioning the self-proclaimed medium. He snuck out his house and carefully made his way to the other's house.

As he stood in front of the door, he wondered what approach he should take. Should he try to play it cool just in case? It could work out either way. If she was the medium, she would feel safe and come along lightly. If she was the mafia or serial killer, she could let the jailer go free and he wouldn't have to worry. Might as well try. He cleared his throat and knocked on the door. He could faintly hear footsteps and heavy breathing. The jailer took a step back when the door opened very slightly, the medium peaking out from behind.

"Y-Yes?" She whimpered, shivering. The jailer wasn't sure she was cold or if she was afraid but he concluded that it was most likely the latter.

The jailer smiled, hoping to calm her down. "I just wanted to question you, if that's sounds alright with you."

The medium gulped. She shakily stepped outside, nodding. The jailer led her back, motioning her to sit down.

"So, you claimed medium, right?" He asked.

"I-I am the medium," She replied, fear in her voice. "Th-The dead... They claim to know who the killer is... Th-They keep yelling at me... Saying that I should reveal it but wh-what if no one believes me?! Wh-What if they're wrong?!"

The jailer raised an eyebrow at this. He quickly wrote down the medium's description of the serial killer before asking her to continue.

"I-I feel like I'm going go insane!" The medium cried.

"Hey, don't worry," The jailer said, smiling. "Everything's going to be alright. You can stay here until morning."

"N-No!" The medium shrieked. "I-I don't... I can't take it anymore!"

The jailer took a step back, confused. "What do you mean?"

"K-Ki..." The medium was sputtering, tears falling from her eyes. "P-Please... J-Just kill me, I don't care! I can't take this! I want them to shut up!"

The jailer stared, too shocked to say anything. She... She wanted to die? That... That was certainly new. Most people he question want to live and for obvious reasons but she... She waned to die? He honestly didn't understand it. He couldn't fathom why. Then again... If he were to constantly hear the voices of the dead, he would go insane, too. He sighed, staring at the medium.

"Do you... Do you really want this?" He asked, hearing his voice falter.

The medium nodded. "P-Please. I hate it... I don't want to listen to them anymore. J-Just make up an excuse on how I kept on claiming different roles every time you asked me a question! I don't care what excuse you make just END ME!"

The jailer bit his lip, unsure if he should grant her wish. The medium looked desperate. She was shaking, face wet and covered with tears, eyes looking around, hands fiddling. To put it lightly, she looked like a nervous wreck. He never thought he would come across this situation. He honestly didn't want to kill her. He had standards for pity's sake! He always had trouble pulling the trigger to kill someone, whether they were guilty or not. And here, the medium is obviously innocent. He didn't... He couldn't...

"P-Please... I'm begging you," The medium whimpered.

He had to. The jailer sighed. "Al... Alright..."

He grabbed his gun and pointed it at the medium's heart. "I-If... If that's what you want."

The medium lightly smiled. "T-Thank you... C-Can I ask you one more thing?"

"Y-Yes?"

"M-Make it quick."

The jailer nodded, and pulled the trigger.


When morning came, the medium, along with the doctor who was killed by the mafia, was announced dead. Interestingly enough, the mafia left a note describing the serial killer, and it matched the medium's description. The town was unsure if they should trust the mafia. After much discussion, they decided to let the jailer take action. And he did.

The so-called-killer didn't say anything for a while. The jailer shook his head, pacing around the other man. He kept asking questions, but received no response. The jailer even tried to threatened the killer, but he still gained no response. He was beginning to get tired. Things were going nowhere. Feeling defeated, he slumped in his chair, rubbing his temples, and tried to formulate a better plan.

"Jester," The sudden voice nearly caused the jailer to flinch. It sounded sad, angry, and possibly frightened.

"You're the jester, huh?" The jailer looked at him quizzically. "Why haven't you tried to get yourself lynched yet?"

"I was hoping it would have happened today in all honesty," The jester hissed. "But no, you just had to agree to jail me."

The jailer sighed. "Well... Looks like you're free to go—"

"Or you can just do a brother a favor and kill me."

What?!

The jailer stared at the jester. "Wh-Wha... Huh?"

The jester was smirking. "Come on... Sure, I would have preferred to be lynched but this will have to do. Besides, the town will be happy. I mean, I am just a nuisance to them."

The jailer shook his head. "No, no. Look, just leave and—"

"Kill me!" The jester hissed. "Trust me, you'll do everyone a favor. The town doesn't have to deal with annoying little me and I get to die!"

He scoffed, throwing his head back. "In case you're wondering why I'm so desperate... I didn't really have a great past... So killing me would end my suffering. I tried to end my life, trust me, but it just doesn't work out. So... Would you kindly help me out here?"

The jailer bit his lip. He was beginning to have some flashbacks to the medium and how she begged him to take her life. He was hoping to let someone go free but no. Another person begging to be killed. He didn't want things to repeat but...

He shook his head. "F-Fine. I mean... If you're that desperate."

The jester was grinning. The jailer would have called it psychotic if it weren't for the fact that it almost looked genuinely happy.

"Sweet. Oh, and one more favor. Please?" He asked a bit too sweetly.

"Y-Yes?"

"Can ya make it quick?"

The jailer almost froze but kept his composure. He sighed, and once again, pulled the trigger.


When day rolled over, only the jester was proclaimed dead. While the town was trying to pinpoint the killer with the use of the wills left behind, the jailer was looking around and listening for anything suspicious. He stopped when he saw two townies whispering to each other, the taller of the two staring at him while the lithe one looked worried. Now that the jailer thought about it, those two had been whispering for the past few days. He decided to jail one of them. Question is... who? He wanted to jail the older one as he looked much more intimidating. However, the younger man appeared to have more information. In the end, the jailer decided to jail him.

He decided to start of with a simple question. "What were you whispering to that other guy?"

The other man bit his lip. "Look, I really can't say anything. I promised—"

"You promised who?" The jailer narrowed his eyes. "Who are you, anyway?"

He man sighed. "Fuck it. I'm the serial killer, happy? You gonna kill me now? Cause in all honesty, that would make me happy."

The jailer raised an eyebrow at this. "Why is that?"

The serial killer snickered. He stared at the jailer, eyes filled with hate, but not towards him. "The mafia has me wrapped around they're finger. They've threatened to punish me. As for the punishment, I don't know. The mafiaoso had a much more... risque threat. The framer just wants to rat me out. Either way, if I screw up, I'm in trouble."

His smile curved into a sneer. "But I know when I'm being tricked. To tell you the truth, I don't really feel like dying to those bastards."

"So, you were whispering to the mafia?"

"Ding, ding! You're right!"

The jailer would have laughed at the remark but all he could muster was a strained smile. "You know who they are then?"

The serial killer nodded. "Yup. Though, the most I can tell you is the godfather. He's the dude I was talking to, and the only mafia member who didn't threatened to snitch or... Do things to me."

"I see..." The jailer mused. "Well, I hope you know that I have to kill you now."

"I am aware of it, and I'm actually kinda happy about it," The murderer was smiling.

The jailer took a step back. A-Again?!

"So, can we get on with it?" The serial killer asked, sounding tired. "I'd rather to someone, er, noble like you than those shitty mafia." He laughed. "Then again, the godfather is probably just as noble as you..."

The jailer didn't know how to feel. Yes, this was the serial killer he was dealing with. But the jailer's morality still kicked in. And to make matters worse, the killer wanted to die, just like the medium and the jester. The jailer honestly didn't know how to feel. He knew he had to end the murderer's life, but he felt like he couldn't bring himself to do it.

"Hey, jailer guy!" The killer snapped him out of his thought. "Look, don't let your damn guilt get ahead of you. You know how happy the town would be if you killed me? Plus, you know who the godfather is. In fact, he could probably rat the rest of the mafia out if he pleased. So... Just end me. I don't want the mafia to be the reason I die."

"Fine," The jailer sighed, loading his gun.

The killer smiled. "Oh, mind making it quick? Pretty please?"

The jailer's breathe hitched. He shook off the sick feeling that boiled in his head.

And the sound of the gun going off filled the room.


As soon as the serial killer was announced dead and the mafia didn't do a thing, the town cheered. The investigator and sheriff appeared to have found out who the godfather was and both agreed to lynch him. The jailer knew they were right and agreed with them. However, a couple of townies spoke up and suggested the possibility of the framer. Needless to say, there wasn't enough time to vote but the jailer knew who he had to question next.

"Are you the godfather? The serial killer told me last night," The jailer said.

"I had a feeling he would rat me out," The godfather chuckled. "Clever..."

"Well, looks like things aren't going to end up well for you," The jailer replied, smirking.

The godfather smiled. "I admit defeat, I admit defeat. Now then, can we get on with my execution?"

The jailer tilted his head. "Are... Are you suggesting that you..." He swallowed the lump in his throat. "You want to die?"

The godfather chuckled. "I guess so... I really didn't do my family justice, anyway. Then again, I always found them to be a bunch of dolts. Crazy, selfish, insane. I honestly regret recruiting them. It would be much better for me to leave them."

He smiled. "Besides, killing me brings you guys one step closer. In fact, I'll bring you guys two steps closer. I'll tell you the last members of the mafia. If I go down, I want to take them with me."

The jailer felt uneasy. This is the fourth time that the person he jailed had wanted to die. And like the case serial killer, he still felt guilt creeping up his spine. But... If it was to help the town and he really wanted to...

He gripped his gun, sighing. Right as he pointed it at the godfather, the older man asked, "May you please make this as quick as possible?"

The jailer just nodded.

And the sound of the gun going of rang in his ears.


"He's guilty," The investigator stated, pointing at the jailer. The sheriff nodded, claiming he found some incriminating evidence.

He looked baffled. The framer. He must have known the godfather would have ratted him out even before his will was presented.. "Look, you read the godfather's will. We know who the last members of the mafia are. We just need to lynch one. Then, I'll jail and kill the last one."

"Or, the godfather is lying," The framer grinned. "You know, kill a random townie?"

The town started to whisper, staring at the jailer.

"Come on, I killed the godfather. He told me who the rest of the mafia is and it matches his will perfectly!" The jailer hissed.

"Sorry man," The sheriff sighed. "There's not enough evidence to prove your innocence."

Before the jailer knew it, he was up at the stand, noose around his neck, stool beneath his feet, faces staring at him. He looked around, shaking. God, why did it have to come down to this? He sighed.

I deserve this.

He looked at the town, smiling as tears began to form.

Everyone... I'm so fucking sorry...

"Hey, can I ask you guys a question?" He didn't care if he was crying. He just wanted things to end. He just wanted to get the punishment he deserved.

No one said anything, but the jailer continued.

I want this to end now.

"Can..." He almost found himself chucking at the irony, smile growing wider. "Can you guys make it quick?"

The town stared at each other, and nodded.

The stool was removed.


A/N: I'm sorry jailer, I really wanted to write this. ;_;