Or it will make him even more a target because he has access to resources.
Also to note most commissary stores have monthly purchase limits. Doesn't matter how much money your account has, you still have the same access to commissary as everyone else.
Having been to prison, folks like Ross (easy target, or, a “sweet lick” as the streets would say…) can and will be targeted for protection and extortion. As far as how folks get things out of him, might well be in the form of commissary or via his family to another inmate account or via his family to an external third party.
There is a deep, twisted hustle economy the likes of which a little casual reading will not educate you on. Consider a great example: fake prostitution listings online, operated by contraband cell phone. Demand payment by hard-to-reverse means, demand upfront payment. Then let them fume as they can’t call the police for an “I got ripped off soliciting sex.”