Dick" Crawford was born in Missouri in 1880 and came to Montana with his parents at the age of three. His father died when Dick was young, and his mother remarried when by the time he was 9 years old. Dick can be found in 1907 in Chouteau County when he marries Mabel McCelland in Chinook. From September 1913 through March 1914, Dick drove the Warrick Stage. In 1914 the Crawford family, with two young daughters, moves back to Fort Benton, where Dick starts a job as a deputy sheriff under Sheriff Rodgers. Mr Crawford won the election to become Sheriff in 1916 and began his service on the Military Draft Registration. The work on this board requires so much time that the Sheriff and another board member request to be replaced for the next year.
In addition to these duties on the Draft Registration, the new Sheriff is busy with more horse stealing, sheep stealing, and now automobile theft. New charges that have not been recorded in Newspapers include bad checks, disorderly conduct, and a rash of illegal gambling because of WWI; he arrested two men on charges of failure to register for military service and, as of December 1917, has eight more suspects to investigate on the same charges. The new year, 1918, brought instruction from Helena for the Sheriff to put into effect a new Montana Law. This law requires every owner of a gun, revolver, rifle, or pistol to register at the Sheriff's office within 30 days. The Sheriff complies but stated that if "every gun in Chouteau County were piled up, a man could not throw high or far enough to clear the pile. In June of 1918, a well-known farmer in the area was arrested on a disloyalty charge. The farmer was alleged to have remarked that he would prefer German rule to that of the United States. Following the end of his term as Sheriff, Dick was again employed as a Stock Inspector, and in 1924, he and his wife divorced. The 1930 Federal Census shows Dick married to Grace and living in Dillon, Montana. The Census of 1940 has Dick and his wife living in Deer Lodge in 1935 and again in 1940 as a guard at the State Prison. Dick died suddenly at home in 1943.
1918- July 1921 Merritt Flanagan was born in 1862 in Missouri. When Merritt was 3 months old, his father died at the Battle of Shiloh. By the 1880 Federal Census, Merritt lived in Lincoln, Missouri, and was employed as a hired hand on a farm. Flanagan went west and ended up in Chouteau County in the early 1880s and was employed as a cowboy and later as a roundup foreman. Merritt married Ida Shanahan in Chouteau County in May 1998. In August of the same year, he was hired by the Federal Customs Service, a job that was headquartered in Chinook. Merritt changed jobs by September 1905 when he moved to Fort Benton to become a Deputy Sheriff of Chouteau County. After two terms as deputy Sheriff, Merritt was the City Marshal of Fort Benton. Flanagan won the election in 1918 to become County Sheriff. During his years as Sheriff, there were more Sheriff Sales in Chouteau County than any other activity. It was the responsibility of the
Sheriff to organize these plans, announce them, and oversee all Sheriff sales. The election in November 1920 placed Merritt as Sheriff for another 2 terms. In July 1921, he was living in rooms above the jail, and after finishing a large meal with one of his deputy sheriffs, Merritt fell down the stairs and died a few hours later of a cerebral hemorrhage at the age of 60.
