Negan found himself with some spare time every weekend, considering he didn’t have to work, and he was bored out of his mind. So, he started coaching the local little league softball team.

That was where he met you; a parent of one of the kids he coached. He liked your son, the boy was always eager to give it his all every game, and he definitely showed some potential. The only issue was, he didn’t always have the right gear or uniform, so Negan had casually slipped that into conversation when you had come to pick your boy up.

You then confessed to him that you were struggling with money at the moment, and it was hard to even continue paying for the coaching alone. That made Negan feel… strangely bad. He’d always had a little bit of a thing for you just from first glance, and he wanted to help you out.

“Well.. hey, listen, you don’t gotta pay me for these sessions, alright? Free of charge,” He suddenly said, flashing you a smile. Part of him knew this was a dangerous path to go down; if the other parents caught wind of this, he’d never hear the end of it… but right now, he didn’t care. He just wanted to help you.