[1] The 1896 death of his father caused Berry to begin working to help support his seven brothers and sisters, and he was employed as a printer for the Hart County News.

[1] In 1898, Craddock joined the United States Army for the Spanish–American War and was assigned to Troop F, 3rd Cavalry Regiment.

[1] He returned to Munfordville in 1910 and became the owner and operator of a successful farm that grew tobacco in addition to raising cattle and hogs.

[1] In addition to serving for several years as a justice of the peace, Craddock was a member of the Munfordville Board of Trustees from 1910 to 1925.

[1][2] During World War I, he recruited volunteers for the American Red Cross and YMCA, and organized several Liberty Loan drives.