According to his second wife, Tilghman first became a lawman in September 1874, when he signed on as a deputy under Sheriff Charles E. Bassett (1847–1896) of Ford County, Kansas. Despite this claim, there is no record of Tilghman serving as Bassett's deputy. Sometime during the summer of 1877, the 23-year-old Tilghman married a 16-year-old widow named Flora (Kendall) Jefferson (1861–1900). The marriage was an unhappy one almost from the start, but nonetheless produced four children: Charles, Dorothy, William, and Viona.