I found this article in the "Sikeston Standard", Sikeston, Missouri, April 17, 1934, page 7. It is part of a larger article entitled 'French Settler Unable to Speak English Well'.
It reads "Dr. Richard J. Waters was a wealthy man, possessor of valuable property in land, which was inherited by his son, Richard J. Waters, who for numerous years was a merchant at New Madrid. This son died in about 1856, leaving a large estate, most of which was divided between his two sons, Louis A. Waters and Dr. W. W. Waters. In 1893, his grandsons, Samuel A. Waters, William W. Waters, John M. Waters and Richard J. Waters were still living in New Madrid county."
Here is the link: https://www.newspapers.com/clip/5729319/sikeston_standard/
If this is your John M., then his father is either Louis or Dr. W. W., his grandfather is Richard J. and his great-grandfather is Dr. Richard J.
New Madrid is close to Sisketon and to the Kentucky border. But I'm not sure if this is your John M.