I' ll bite, I' m curious to see where this goes...

Young fellow in the twentyish era, I would think he looks at himself as Mr. Hottie Tottie that thinks he is a bad A$$ and wants to look dangerous. More than likely trying to draw attention to himself, scare the punks and impress the skirts. Maybe running a crew or just wanting to make a name for himself.

The forties guy could possibly be an officer of some type or a skip tracer. But with no badge visible, he could just be someone that has been mugged a few times and wants to keep the idiots off him. My guess would be more than likely that it is a job related liability or protection requirement.

That is how I would look at them in the situation, so what are the real conditions? Where are you going with this one? Or better yet, what happened to whom?