It's been said that the James-Younger Gang were part of a secret society called, I believe, the Knights of the Golden Circle which was a network of influential Confederate-sympathizers after the war. With being members of that group, they were awarded protection for their actions. One of the stories is that James was part of the network that helped finance resistance to Reconstruction in the South, partially through his robberies and partially by aiding in the transport of other funds raised by the Knights. Now I don't know how true this is but if it was, you could at the least consider James an OC figure in that he ran rackets (armed robbery, money laundering, etc) for an underground organization with a great deal of political and economic influence. But who knows?