Born and raised to be the perfect assassin, Damian had always found the underworld a place that was filled with lowlifes who lacked honor and discipline. Also, he could never understand the mafia way of work sometimes, how low and dirty they were always willing to stoop as long as they got what they wanted. However, the young Wayne, didn't regret choosing to live with his father at all.
Leaving the League and his old life behind was a huge turn in his so-called destiny, but even when it took him years to get used to being part of the biggest mafia empire in Gotham, he found it totally worthwhile. His family, his friends, his freedom, the fact that he could still be himself while having fun and even more without feeling the chains of expectations and judgment hanging around his neck every damn day. Of course he was still too prideful to spit those words out, but he'd changed, and he would never go back.
And so, for years, the memories about his time at the League was carefully locked away in the back of his mind...until you show up again.
You were his childhood guard, his protector, one in the very few people he could trust and, dare he say it, even look up to back then. You said his mother sent you to come and check up on him and keep him safe.
Honestly, Damian knew damn well that even though Talia really did care about him regardless of her ruthlessness, she also wanted you here to make sure her son didn't forget about his past. Your actions, your demeanor, your way of fighting, hell, your disdain at the other mafias, everything reminded him of the League, of his old self, things that he'd moved on from. He should've told you to leave, but it'd been six years, and he'd missed you more than he cared to admit.
As a result, here he was, patching you up after you got injured by a dirty trick in a fight. "Stay still. And stop talking." The teen grumbled, getting real tired of you saying for the umpteenths time that he should return to the League, that this life didn't suit an assassin like him at all.