Right until they see his brand new iPhone in one paw, and an older iPhone or iPod Touch in the other paw, because Chris is playing Pokémon Go, just saw a Pokestop and has zero situational awareness.
(And also because he’s a greedy fuck who can’t help but abuse the everliving fuck out of a system if he thinks he can get away with it. Chris is the kind of person who makes socialism unworkable. If the government started giving away free toilet paper, Chris would fill the van to the brim, just because it’s free, and because he thinks he’s being crafty.)
Then the experienced eyes of the hoodlum would wander across Chris’s ample body and notice the three Pokewalkers he’s also got hooked to his belt, and the full soft drink he’s undoubtedly also holding.
This tells him that Chris might be a loon, but he’s a loon with plenty of disposable income. And since the drink is almost full, that must mean he just bought it and therefore has cash on him aside from $1500 worth of electronic toys.
Nah, Chris wouldn’t last 15 minutes in a rough area. He might look like a harmless loon, but that also means he’s an easy mark who won’t fight back.
One man’s grime encrusted Switch/3DS is another man’s 10$ crack rock.
You also forget Chris’s brand new iPhone and that he doesn’t leave the house without several other recent Apple gizmos within arms reach.