I heard this phrase in a TV show. Two characters are drinking in the scene, and one of them is not pleased with the low quality of the alcohol brought by the other person. The conversation goes like this:
A: Where did you get this swill, man?
B: It's a celebratory gesture. We open, we sip, we move on with our lives. Everything does not have to be top-shelf foodie porn.
A: Yeah, but you didn't have to roll a hobo to get it.
What does "roll a hobo" mean here? I found that "hobo" means "homeless, poor person", so I guess the sentence means something like "you don't have to act like you're that poor". I'm still not completely sure though, because "roll" has too many different meanings, and I could not find any reference to the phrase "roll a hobo" online. Does anyone know what the correct interpretation is?