Copyright caymancompass
For six decades, the Cayman Compass has chronicled the triumphs, trials and transformations of these islands. In that time, ownership has changed hands only a handful of times, each transition preserving a singular mission: to inform, to educate, and to connect the Caymanian community. When Dart Media and Entertainment, owned directly by investor Ken Dart, acquired Compass Media in 2023, it did so not to reinvent that mission, but to reinvigorate it. Following James Bergstrom’s steady leadership through some of Cayman’s most challenging years, Dart saw an opportunity to strengthen the country’s next chapter by investing in the institution that has documented all the others. Act of renewal Ironically, the company’s first act of renewal looked backward, not forward. During a post-acquisition tour of Compass Media, board members came across racks of bound newspapers and boxes of negatives – an untouched visual history of Cayman. On the spot, they decided that this story deserved to be preserved. From that moment, TimeBack and the Cayman Compass Digital Archive were born, modern platforms making decades of Caymanian history accessible to anyone, anywhere. From there, investment turned toward the future: technology, infrastructure and people. New equipment, new journalists and new leadership under publisher Tripp Donnelly, whose entrepreneurial background in technology helped transform Compass into a truly omnimedia company: uniting print, digital, radio and television under one modern newsroom. In 2024, Dart’s belief that journalism should be accessible to all led to the removal of both the online paywall (a necessary mechanism during the lean pandemic economy) and the $1 newsstand fee, making the Cayman Compass free to everyone in the community it serves. Return of TV The most visible symbol of renewal, however, was the return of television to the Cayman Islands. Nearly six years after the closure of Cayman 27, Compass TV launched, a purpose-built studio housing a new generation of journalists, producers, and storytellers, supported by the latest newsroom technology. Radio expanded its reach, ensuring residents across Grand Cayman, Cayman Brac, and Little Cayman could access every facet of Compass news and entertainment. From a single newspaper to an omnimedia platform, Compass Media’s journey mirrors that of the Cayman Islands itself – grounded in legacy yet propelled by innovation. Today, the refreshed Shedden Road complex stands as both a physical and symbolic reflection of this evolution: heritage and modernity, side by side. Responsible journalism None of these investments would exist without Ken Dart’s conviction in the enduring value of responsible journalism, a conviction shared by every Compass owner before him. That belief runs deep: the Dart family’s commitment to supporting journalism dates back more than three decades through the Dart Center for Journalism and Trauma, initiated in 1994 and based at Columbia University from 2009 to 2025, which has supported ethical reporting and journalists worldwide. Dart Media and Entertainment and Compass Media operate independently from Dart Enterprises, a small but meaningful distinction that underscores the point. The mission here isn’t commercial; it’s civic. To preserve Cayman’s story. To strengthen its voice. And to ensure the next 60 years of the Cayman Compass remain as vital as the first.
