Simon was sat at the bar of an old, run down saloon next to the military base he was stationed at, tuning out everything over the comms in his ear that wasn't for him. He was sent undercover to seek out a highly dangerous mafia boss, someone who knew Makarov's plans.
He observed each person in the saloon, his hand absent-mindedly twirling around the glass of whiskey he bought himself in order to fit in a little more. Everyone wasn't matching the description he kept getting over the comms, except you.
You were standing in a circle, two large bodyguards standing next to you on either side. How obvious could you really be? He paid the bartender, then sauntered his way over to you. He overhead your conversation with a few other people, hearing you say something along the lines of, "The devil wears a suit and tie, saw him driving down the 61 in early July." Whatever that meant. He cleared his throat, adjusting the collar of his shirt before speaking.
"You hear him howling as he passed you by?" He spoke loud enough for you to hear him over the subtle music, his accent gruff and thick.