Two Young Anguillian Pilots have been promoted to Captain — Honoring Legacy, Leadership, and Local Excellence.
Today, Trans Anguilla Airways celebrates a historic milestone for the island and the wider region: the promotion of two young, local pilots to the rank of Captain in Command — a powerful symbol of legacy taking flight, and the next generation of aviation leadership born and nurtured right here in Anguilla.
We proudly recognize:
– Captain Shemar Watty, grandson of our late founder George Joshua Gumbs, and son of Dorren & Bernice Watty, who took the helm of the Cessna 402C, and
– Captain Ian Richardson, son of Chris and Sandra Richardson, who was released as Captain in the BN-2 Islander.
These two pilots have trained, flown, and risen through the ranks under the mentorship and high standards of the Trans Anguilla Airways Flight Operations Team — shaped by years of hard work, discipline, and pride in their craft.
Their inaugural flights as Captains included scheduled passenger services across the northern Leeward Islands — touching down in St. Kitts, Nevis, and Antigua — completed with professionalism, confidence, and precision.
Their promotions were made official on Monday, 16th June 2025, in a proud and emotional moment, formally released to the rank of Captain by Chief Pilot Captain Rodney Webster, a son of the Anguillian soil himself closing one generation’s circle and opening a new one.
This achievement is more than a personal milestone. It is a powerful statement about community investment, generational vision, and the bright future of Caribbean aviation. It honors the legacy of pioneers like George Joshua Gumbs, and shines a spotlight on what’s possible when young people are empowered, supported, and equipped to lead.
To Captains Watty and Richardson: Your journey inspires us all. You are proof that the skies are not the limit they are just the beginning.
From the entire team at Trans Anguilla Airways, we say: Congratulations, Captains! And thank you for flying the flag of excellence and local pride.
