he could make some calls and barter those for deposits on his commissary account? If the calls are good he may also build cash accounts outside the prison system?
There are guys in prison who have done this, but it's not easy. And some prison systems try to prohibit this sort of thing. The policies are not consistent, even within each prison system, so, for example, the warden at one state prison in Wyoming may have different ideas or priorities than the warden at a different state prison, even within Wyoming. One may ignore this kind of activity while the other makes it a personal project to stamp it out.
Almost every prison system in the USA has a policy which prohibits prisoners from "operating a business" while they are incarcerated. But some policies allow the warden to make an exception.
Of course, many would argue that the activity in question is not a business in the traditional sense of the word, but rather a sophisticated form of investment. But prison systems have very wide latitude to interpret their own policies however they want. And the courts are reluctant to interfere unless there are very clear violations of the most basic constitutional rights.
If you were to officially ask this question, i.e., ask a prison warden or the director of a state corrections agency whether prisoners can trade stocks or other securities, you would probably be told that the only appropriate way to do it is for the prisoner to communicate with his attorney, or possibly a nonlawyer who holds power of attorney (like a spouse or family member) to give instructions on what to do with funds in
their own account. So, yes, to a certain extent prisoners have some right to direct the management of their personal financial affairs from behind bars.
But calls, letters and e-mail to anyone other than an attorney can be monitored. If a prisoner was caught giving advice or recommendations to outsiders, and getting compensated for that advice, that could lead to trouble, and they could also try to confiscate the money that the prisoner received.
With that begins said,
yes, some prisoners do get away with this sort of thing, but it's not easy. In many systems deposits to the prisoner's account can only be made by a family member, an attorney, or a person who has been approved to visit the prisoner in person. So to get money from a third party into the prisoner's hands or into his control, they have to have a network on the outside that is willing to move the money through the right channels.
If the amount of money is significant, then it can't be moved around without creating an electronic trail, and that exposes the people on the outside (e.g., spouse, attorney) and the money itself to some risk.
