Darrell Richardson remembers exactly where he was when the call came. A friend — a retired airline executive — rang him up with a simple question: “Did you hear they’re selling Seaborne?”
He hadn’t. But within days, Richardson was on a flight to the Virgin Islands, pitching the opportunity to his most trusted investors. “I made one phone call,” he said in an interview with the Source Saturday. “Two days later, we bid.” And just like that, one of the region’s most iconic carriers — and the world’s only Part 121-certified seaplane operation — had a new owner.
For Richardson, now president and CEO of Seaborne Airlines, the challenge wasn’t new. He’s built a career out of turning around struggling carriers. After stepping in at Silver Airways following its 2010 bankruptcy, he rebranded the airline and led it into growth before retiring in 2013, long before its more recent financial collapse. “This is what I do,” he said simply.
This time, he wasn’t working alone. Behind the swift acquisition was the Leonite Fund, a New Jersey-based investment firm with a reputation for supporting small businesses poised for growth. Richardson had worked with them before, describing the relationship as one built on trust. “They’re probably my favorite investors when it comes to putting these types of packages together,” he said, adding that after calling to pitch the deal, they said yes immediately. “Two days later, we had the bid in.”
That confidence was echoed publicly. In the official sale announcement, Leonite Fund’s Chief Investment Officer, Avi Geller, praised Richardson’s ability to bring “tighter operations, reinvigorated team culture, and sustainable profitability.” With Richardson’s leadership and Leonite’s financial backing, Seaborne suddenly had what it hadn’t had in years: a clear path forward.
That path started immediately. Just days after the deal closed, Richardson was in the territory, riding the seaplane for the first time. “It was fantastic,” he said, still sounding awed by the experience. From airport gate agents to hotel staff, everyone he met had their own Seaborne story. “Everyone’s flown on that plane,” he said. “It’s part of the community.”
That sense of connection is exactly what he hopes to protect and grow. While the history and nostalgia tied to the airline are undeniable, Richardson knows sentiment alone won’t secure Seaborne’s future. Practical steps are already underway.
“There’s no break in service,” Richardson stressed. Flights will continue as scheduled, with the same familiar faces in the cockpit and on the ramp. But behind the scenes, change is already in motion: a full review of the fleet, pay raises tied to company growth, and a customer service training overhaul designed to restore the warm, welcoming experience Seaborne was once known for. “We need to get back to being the airline people are proud to fly,” he said.
At the core of Richardson’s strategy is Seaborne’s greatest asset: its coveted Part 121 certification. The rigorous federal standard required of major carriers like Delta and American sets Seaborne apart as the only seaplane operation in the world held to that level. “That means two engines, two pilots, and all the safety checks of the big airlines,” Richardson explained. “And that matters.”
For now, Seaborne’s twin-engine De Havilland Otters will continue flying between St. Thomas and St. Croix. But Richardson sees more on the horizon. He envisions expanding the fleet to four or five aircraft and restoring service to destinations across the Caribbean, including Vieques.
What makes the work personal is the people. His message to staff was clear from day one: “As we grow, you grow.” He knows the strain employees have carried through Seaborne’s years of uncertainty. Now, with Leonite’s support and a leadership team focused on long-term sustainability, Richardson is promising stability, opportunity, and a future. “We want to be part of this community. This isn’t just another airline to me.”
It’s a lesson Richardson learned at Silver Airways, where he guided the company from bankruptcy to industry awards before stepping away. “I know what it takes to rebuild,” he said. “And I’m not going to let Seaborne end up in financial trouble again.”
There’s a new slogan in the works: “Wings Over the Caribbean.” But for Richardson, it’s not just a tagline, but a commitment to safety, to service, and to the islands Seaborne calls home. And, the priority is simple: keep the planes flying, keep the service reliable, and rebuild trust, he said.
“We’re going to build something this community can be proud of again,” he said.
