Supernatural: Wayward Sons: Monster Squad

Jack Goes To Hell: The Final Friday of the Month

A Long Time Ago

"John, what do you do for a living?" 13-year-old Adam Milligan asked his father as they stood in the small bar where John Winchester was teaching son how to hustle pool. This was only the third time Adam had spent time with his father since learning of his father's existence and was honestly growing to like the old man despite his inner voice telling that John would only hurt him if he got too emotionally attached.

"It's very difficult to explain," John told him. "Let's just say I'm in the business of helping people.

"Are you a doctor?" Adam asked as he lined up his shot and hit the ball, sending it rolling into the ball near it and sending it sinking into the nearest hole. "Or a firefighter? Don't tell me you're one of those guys who has to test those rectal thermometers before they leave the factory."

"Like I said, it's complicated," John told him, realizing how snarky Adam was. Dean was the same way and wondered just how well the two would get along if they ever met. But John knew that he had to keep his secret son as far away from that life as possible. "Maybe someday I'll be able to explain it better, but for right now—"

"Yeah, yeah, I'm too young, " Adam told him. "That's what Mom always says when I want to do something fun like getting a tattoo or skydiving naked."

"You listen to your mom, she knows what's best for you and just wants you to come home safe," John told him. "There's a lot of bad people in this world, son. People that want to see you hurt."

"Like the guy that hit me with that car?*" Adam asked, not knowing it had been Azazel that had struck him in an attempt to strike at John Winchester.

(*WWS #12)

"Exactly," John told him, cursing himself for not being there when Adam needed him. He'd seen Adam's scarred body when Adam had changed shirts in the car earlier after teaching him to change the oil in the Impala this morning, knowing he might not ever have a normal relationship due to it. "You saved your mom's life and I couldn't be prouder. And you don't let anyone tease you about that scarring, you hear? Those are battle wounds and you're a brave boy for defending your mom like that. You keep that courage in your heart, kid. Someday you're going to do great things."

John looked over at two easy marks that had just walked into the bar. "Ready to put those hustling skills to the test, Adam?"

"Yes, sir," Adam smiled. By the end of the afternoon, Adam would be sent home with $1000 in spending money that he'd never tell his mother about although he would buy nice little things for her to show his appreciation.

*

"You were kind of a prick, John Winchester," Adam said as he stood in the bar bathroom as he splashed water on his face. Adam's view of his father had changed drastically upon learning about how his older brothers were raised as soldiers from a young age. He felt sorry for Sam & Dean and vowed that the same fate would never befall his own son. "But you were right. Raphael took my friends, but that's all he's going to get. I have to be courageous for the friends I have left. I may die, but Hunter's going to live, no matter what. Just have to figure out how to stop that dick with wings."

*

At the Men of Letters bunker, Jack packed any supply he could think of into a backpack.

"Where are you going?" Castiel asked.

"Hell," Jack simply replied. "I'm rescuing Cole before he's tortured any further."

"You are nowhere near strong enough to take on Raphael," Cas said. "He'll easily recapture you and we'll be another man short."