When his family's finances collapsed, Davis (then 15 years old) abandoned his education and took a job carrying water for workmen at a nearby quarry, then became caretaker of "Waverly" a nearby farm own by Governor Howard. When Davis was 20, the B&O completed track from Frederick to Cumberland, and needed men to run the trains and handle cargo. Thus Davis went to work for the Baltimore and Ohio Railroad as a brakeman. His hard work and enthusiasm drew the attention of the railroad's president, Thomas Swann, who promoted him to freight conductor, then passenger conductor. Davis met many statesmen, including Senators Henry Clay of Kentucky (whom Davis came to admire and received invitations to visit at his home), Thomas H. Benton of Missouri, Lewis Cass of Michigan, Benjamin Wade and Thomas Corwin of Ohio, and Stephen A. Douglas of Illinois -- all of whom embarked the B&O train in Cumberland to reach Washington, D.C. (or disembarked on the reverse route). Davis also often stayed at a hotel in Washington between trips, and conversed with other notables, including Senators William C. Rives of Virginia, John C. Calhoun of South Carolina, and Daniel Webster of Massachusetts.