Five months later his wife, Alice, and his mother died on the same day. Grief stricken, Roosevelt decided to leave the East and increase his interests in the cattle business. In March of 1884 he wrote to Bill Sewall, his hunting guide on an earlier hunting trip in Maine:
"I hope my Western venture turns out well. If it does, and I feel sure that you will do well for yourself by coming out with me, I shall take you and Dow (another Maine woodsman who had served as Roosevelt's guide) out next August. Of course it depends on how well the cattle have gotten through the winter. The weather has been very hard and I am afraid they have suffered somewhat; If the loss has been very heavy I will have to wait a year longer before going into it on a more extended scale. So, as yet, the plan is doubtful."
After attending the 1884 Republican convention in June, where the candidate he was backing lost, Roosevelt left for the Dakota Territories to look for solitude. His cattle had wintered very well so he decided to put in 1,000 more head and "make it my regular business." During that visit, Roosevelt selected the location for a second ranch, naming it the Elkhorn. He purchased the rights to the site, located thirty-five miles north of Medora, from the previous occupant for $400.00.