The Caldwell family worked in the newsprint business for three generations in the Mississippi and Arkansas Delta. This heritage began with Henry T. Caldwell (1867-1942) who abandoned farming in his 30s for a new profession in printing. He soon learned the use of a linotype machine, that generates the individual lead type letters that constitute large blocks of the print for newspaper pages. Henry printed and managed a newspaper in his native Mississippi almost forty years. He versed his son, Roy H. Caldwell (1901-1957) in the printing trade. After graduating from high school in New Albany, Mississippi, Roy relocated to Madison in St. Francis County, where he operated a linotype machine for a local newspaper. By the 1930s, he served as "printing foreman" for a different paper in Forrest City. Roy also trained his young son, Marvin Caldwell (1926-1983) in the printing trade. By 1949, they each had purchased half ownership of the historic newspaper, "Courier-Index" of nearby Marianna and moved there to edit and publish it. They expanded the business, adding a custom print shop and office supply store. Marvin and his wife Dorothy gained full ownership in 1957 following his father's passing. He ran the firm with the help of his family until his death in 1983. Dorothy owned and managed the operations herself briefly before selling the "Courier-Index" to a regional media corporation in 1985.