The common thread running through the various incarnations dating back 128 years is Walter Willard Thompson, who gained prominence as the editor of the historic weekly Key of the Gulf.
The pair changed the name to the Key West Citizen and continued to operate it as a weekly newspaper.
"My grandfather, L.P. senior went to New Orleans to buy the machine but found that he didn't have the money," said grandson Greg Artman, a retired Monroe County sheriff's deputy.
It was Norman Artman who decided in 1957 to discontinue the Saturday Key West Citizen, replacing it with a Sunday edition.
Though he professed interest in keeping the paper in the family, he sold it - and the Artman Press, which handled commercial printing jobs - to Charles D. Morris for $2.5 million in 1968.
In 1985, the paper became a morning edition, and by the summer of 1988, had moved to its present location at 3420 Northside Drive, the largest office it had ever occupied.
In 1989, Thomson invested in a Goss Community press and a new computer system that brought The Citizen in line with the rest of the newspaper world.
But by February 2000, Thomson announced plans to divest itself of 54 small papers in the United States and Canada, in order to focus more intently on its databases and other cyberspace holdings.
On June 21, the Key West Citizen was sold to John Kent Cooke Sr., scion of a family with strong roots in newspaper publishing: family patriarch Jack Kent Cooke, who had been involved in a number of joint newspaper ventures with Thomson in Canada, once owned the Los Angeles Daily News, as well as a group of community papers in Arizona, Colorado and New Mexico.