A Cherokee Freedman, Rogers was related to Clement Vann Rogers the father of Will Rogers, the Oklahoma humorist.
He was often in the company of Bass Reeves, but worked under the direction of U.S. Marshall Crump.
Often many of the persons that Rogers assisted in handling were later tried in the Ft. Smith Courts.
His most famous effort however, was his part in the capture of African Cherokee outlaw Crawford Goldsby–Cherokee Bill. In addition to the work that he occasionally performed with Reeves, Rogers also worked with Rufus Cannon in the Choctaw Nation.