Cayman Airways captain completes final flight with son as co-pilot

Cayman Airways Captain Joseph ‘Joey’ Jackson brought nearly 45 years of distinguished service to a close on Feb. 4 with a moment few pilots get to experience – his final flight was flown with his son, First Officer Bradley Jackson, serving as his co-pilot.

The historic father-and-son pairing marked Jackson’s retirement flight and served as a powerful symbol of mentorship and generational legacy within the Cayman Airways flight operations team and the wider Caymanian aviation community.

“Flying my final flight with my son beside me in the cockpit was incredibly meaningful,” Jackson said. “Aviation has given me so much over the years but sharing that moment with Bradley was something truly special. It brought my career full circle, from my first flight as a young boy, to ending my airline career flying alongside my son. That’s a memory I’ll carry with me forever.”

Echoing those sentiments, First Officer Jackson said the father-and-son bond they experienced that day was like no other, and one he never wanted to end.

“Being my dad’s co-pilot on his final flight was the proudest moment of my life,” he said. “I had always known he was the most important person in my world, an absolute legend in my eyes. But when we pulled onto the ramp that day, I realised that belief wasn’t mine alone. It was shared by all of Cayman Airways and by many residents of the Cayman Islands. His commitment to safety, professionalism and mentorship has influenced countless pilots, including me, and I hope one day I can live up to the standard he has set, both in aviation and in life.”

The father-son duo was also joined on board by several family members for this special final flight, which was KX105 from Miami to Grand Cayman. The Cayman Islands Fire Service conducted a customary water cannon salute as the aircraft taxied to the ramp, where a special Guard of Honour was formed to greet and pay tribute to Jackson. Cayman Airways executives, officials, board members, pilots, crew and employees were joined by a large contingent of government ministers, members of Parliament, the deputy governor and other officials led by Premier André Ebanks.

Jackson joined Cayman Airways in 1981 and has been a defining figure in the airline’s modern history, flying through multiple fleet transitions while earning a reputation for professionalism, sound judgment and an unwavering commitment to safety. Over the course of his career, he also served as a designated flight examiner and played a leadership role in strengthening safety standards, including contributing to the airline’s first IOSA audit and certification.

Speaking at a retirement celebration held in his honour at George Town Yacht Club right after his flight’s arrival, Minister for Tourism and Trade Development Gary Rutty praised  Jackson’s impact as both a pilot and a national ambassador.

“As a Caymanian pilot flying for Cayman Airways, Jackson represented our country every time he took his seat on the flight deck,” Rutty said. “He was not just transporting passengers – he was serving as an ambassador for the Cayman Islands, embodying competence, calm leadership and pride in who we are as a people.”

Rutty also highlighted the significance of Jackson’s final flight alongside his son.
“That moment captures his legacy beautifully – a reminder that his career was not just about flying planes, but about passing knowledge to the next generation,” he added.

Chairman of the Board of Directors of Cayman Airways David Ritch, reflected on Jackson’s contribution from a governance and stewardship perspective. “Over nearly forty-five years, Captain Jackson has been one of those people on whom Cayman Airways could consistently rely,” Ritch said. “He represented the very best of what the Board expects from those entrusted with command, demonstrating sound judgment, professionalism and a deep respect for the responsibility that comes with flying an aircraft carrying passengers, colleagues and the Cayman Airways name. These are qualities that do not appear in manuals but are built over time through character and experience.”

Cayman Airways president and CEO, Fabian Whorms, described Jackson as a steady and deeply respected presence throughout decades of change at Cayman Airways as well as in Cayman’s aviation industry.

“Through fleet changes, industry challenges and the country’s periods of growth, Captain Joey remained someone that many of us simply came to rely on,” Whorms said. “His quiet confidence and integrity helped shape the culture we are proud of today at our national airline”.