In the winter of 1879, while the family was struggling to survive in Carrollton, Missouri, a neighbor, Captain Wolfold came to see D.S., James oldest son, and explained that the Northern PacificRailroad was building a steamboat called the "St. Louis", to go up the river to Bismark and he was to be the captain. He asked D to go with him on the initial trip, so brother Meriot was left in charge of the ranch and D started off on many adventures. At that time steamers could go as far as the Yellowstone River. Although D knew nothing about steamboats, Captain Wolfold offered him a job. They stopped in Bismark where they used the steamboat to take a railroad engine across the river to Mandan for the railroad extention being build by the Norther Pacific westward from Mandan.
It is unknown how many trips D made up and down the Missouri on "The St. Louis," that summer, but we do know he had serveral jobs on the steamboat from dishwasher to actor and singer. We have one picture of him in a costume on board the ship. This is the earliest picture we have. He was probably 24 years old at the time. The next fall he took a horseback ride up to Deadwood, N. D. for a few weeks, then spent the winter in Denver. The next spring, he returned to the Black Hills town and was offered a job as a jailer by Sheriff Garland. He stayed on as jailer for the next four years even when Sheriff Garland was replaced by Sheriff Manning. Here we begin a series of interesting stories from wild west days in Deadwood.