The Macon County Times celebrated its 90th Anniversary in 2009.
Founded in 1919, the Macon County Times is the county's second-oldest business next to Citizens Bank. Although it was registered with the Tennessee Secretary of State on April 12, 1920, the Times began publication in Lafayette the week of May 27, 1919. There were several men who were instrumental in the Times' founding. James Ragland, general manager, was a farmer and large landowner, who had served as sheriff in the first decade of the 20th century. J.M. Chamberlain, whose son James Chamberlain served as a local attorney and Judge for the City of Lafayette before his death, was office manager and associate editor. The first editor was J.M. McDonald, who later became an attorney. W.E. Carter, the grandfather of Lafayette Mayor J.Y. Carter, was general manager. J.B. Freeman served as secretary in the 1920 incorporation papers. He was the son-in law of Woodmore Hotel owner Moses Woodmore and became a Lafayette business entrepreneur and county-wide office holder. Other early members of the staff are Dr. M.H. Allen and Fred F. Fishburn, who served as the newspaper's treasurer. In 1930, Calvin Gregory, a school teacher and Missionary Baptist preacher, moved from Pleasant Shade in Smith County to Lafayette and purchased J.B. Freeman's half interest in the paper. Ragland remained as part owner and general manager until 1939, but Gregory became editor in 1930. He retained that position until his death in 1957.
Gregory grew the Times from a four-page weekly, and, by the time of his death, the publication had the seventeenth largest circulation of any weekly newspaper in Tennessee's 95 counties. In addition to putting out the paper each week, Gregory ran the paper's print shop and oversaw local delivery of both Nashville daily papers, The Tennessean and The Banner. He also continued his work in the ministry and wrote the popular "Cal's Column" for the paper. Gregory was also pivotal in the founding of North Central Telephone Cooperative, which brought telecommunications to the area for the first time. He made the first call to the Rural Electrification Administration on June 1, 1954, the time of the official "cutover". He was also the first president of NCTC and was influential in the founding of Tri-County Electric Cooperative in 1937. Gregory left the operation of the paper in the hands of his two sons Leonard and Charlie. Leonard operated the paper from 1957-1965 before making the decision to leave Macon County and leaving the paper in the hands of his brother Charlie, who ran the paper and its print shop until his passing on Dec. 30, 1991 after a valiant battle with cancer. Gregory's daughter Cindy took on the role of business manager after her father's death and remained until 2008. In 1993, the newspaper left ownership of the family, and Truett Langston took on the role of publisher. He retired in 2005.