The paper traces to October 1965, when Caymanian businessman Billy Bodden launched The Caymanian Weekly. A rival weekly, the Cayman Compass, started in 1972, and the two merged in 1974 to form the Caymanian Compass, with Brian Uzzell taking over as majority shareholder that same year and running the business for roughly four decades. David and Vicki Legge's Pinnacle Media acquired Cayman Free Press in June 2013 and restored the shorter Cayman Compass name in May 2014. Attorney James Bergstrom bought Pinnacle Media in 2019, and in 2023 the Dart group acquired the company, now Compass Media, which also operates the Hurley's Media radio stations including Z99. Today, the Cayman Compass is mainly focused on Cayman Islands government and Parliament, elections, financial services and offshore regulation, business, crime and courts, education, and community news, alongside coverage of the wider Caribbean, from their headquarters in George Town, Grand Cayman, Cayman Islands. One interesting fact: The masthead has died and come back. The original Cayman Compass published its final edition on 12 June 1974 before merging into the Caymanian Compass, and the name sat unused for forty years until new owners revived it in 2014.