It probably depends on how serious the crime was, I would think. Which would require us to know what he thought he was doing. Intent would matter, I would think.
For example, if the dude just randomly picked your pocket and had no idea it was all you had, I think that’s slightly less evil than if he gloatingly snatched your last dollar from between your fingers while tossing you out on the street, grinning cheerfully while he predicted your impending death from exposure.
Which (I’m thinking as I write this, bear with me) leads me to think that there are two separate problems here - the taken money, and the intent to harm. So what was guy 1’s intent? Perhaps he was on his last dollar. Perhaps he was young, didn’t have any money, and was struggling with a couple of jobs while going to school. (It does of sort sound like they might have been comparable economic circumstances, since they apparently shared the apartment.) Why should we think he in any way intended to impart hardship - perhaps he just felt he needed the money. Or perhaps he just forgot about it. It doesn’t seem like guy 2 came after him for it - perhaps he didn’t even realize he was causing any problems?
Guy 2 is basically seeking punitive damages. But I think for those to be merited you have to show some sort of callousness on the part of the guilty party. Don’t you?