Caymanian 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 Wednesday February 4, 2026 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 Captain 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,” Captain 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 realized 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 (MIA) to Grand Cayman (GCM). 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 Capt. Joey. Cayman Airways executives, officials, board members, pilots, crew, and employees were joined by a large contingent of government Ministers, Members of Parlaiment, the Deputy Governor, and other officials led by the Premier, the Hon. Andre Ebanks.

Captain Joey 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. Most of the airline’s current contingent of pilots received their wings thanks to Capt. Jackson’s proficient training, as well as the tremendous example he set.

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, the Hon. Gary Rutty, praised Captain Jackson’s impact as both a pilot and a national ambassador.

“As a Caymanian pilot flying for Cayman Airways, Captain Jackson represented our country every time he took his seat on the flight deck,” Minister 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.”

Minister Rutty also highlighted the significance of Captain 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, Mr. David Ritch, reflected on Captain 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,” Mr. 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.”

Mr. Ritch also noted the broader meaning of the shared cockpit moment between father and son.

“There is something powerful in knowing that the values we hold dear - professionalism, pride, and service - are being passed from one generation of Cayman Airways pilots to the next,” he said.

Cayman Airways President and CEO, Mr. Fabian Whorms, described Captain 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,” Mr. Whorms said. “His quiet confidence and integrity helped shape the culture we are proud of today at our national airline”.

President of the Cayman Airline Pilots’ Association (CAPA), Capt. Troy McCoy, stated: Captain Jackson’s unwavering commitment to excellence has not only elevated the standards of our industry but has also inspired those around him. His leadership and mentorship have fostered a culture of respect and teamwork, ensuring that every crew member feels valued and empowered. As we celebrate his remarkable career, we recognize the lasting impact he has made on our organization, and the countless lives he has touched. We wish him all the best in his future endeavors, knowing that his legacy will continue to guide and motivate us all.”

Capt. Jackson said that touching down at Owen Roberts International Airport on Grand Cayman for the last time made him more emotional than expected. “There was a deep sense of pride, gratitude, and reflection all at once,” he said. “I thought about where it all began – the many aircraft I have flown, the colleagues I’ve worked alongside, and the countless passengers we safely brought home. It was a very special moment and one I will never forget.”   

His hope for Cayman Airways is that the airline continues to do what it has always done best – operate safely, professionally, and with pride for the Cayman Islands.

“For the pilots following behind me, respect the responsibility that comes with this profession, never stop learning and always support one another,” he said. “This airline has always been about people. I trust that this will continue to stay at the heart of it and Cayman Airways will continue to thrive.”

Captain Jackson’s retirement marks the close of a remarkable Caymanian aviation career - one defined not only by technical excellence, but by leadership, mentorship, and service to country. His legacy will continue to fly on through the pilots he trained, the standards he upheld, and now, through his son, who carries that tradition forward in the cockpit of the national airline.

Photos by Paul Tibbetts