I've seen this on TV.
There was an old series, Bugs, which had a rather cool prison escape. The tech-genius villain made a deal with the prison operator: They give him external communication, he applies his great financial skill to run a share trading and business operation from within his cell. No-one need know the mysterious CEO is a prisoner. The scheme is a huge success, the warden gets rich, the villain gets richer... until he has enough wealth to simply buy the prison and order his own release. By the time the prisons authority figures out what happened he is long gone.