Rexy Rolle Soars with Family Airline Built on Brains and Belief

Flying over the turquoise blue waters of The Bahamas while sitting in the cockpit with your dad could put any child’s head in the clouds. The influence her parents had on Sherrexcia “Rexy” Rolle gave her the ability to stay grounded and still dream.

“That is why I am big-eyed, meaning I think I can take on the world at the end of the day,” says the vice president of operations and general counsel of Western Air Limited. Her family’s company is the largest privately-owned airline in The Bahamas. Rolle, her parents and some of their relatives celebrated a new milestone in June with the arrival of the first of three Embraer-145 SA long-range jets added to Western’s fleet of planes. “I’m in a rare situation of being able to build upon a family business or a family legacy that has already been established, but I don’t take that with ease,” says the aviation attorney.

It seems Rolle rarely takes anything for granted with the drive for excellence Rex and Shandrice-Woodside Rolle instilled in their daughter. Rolle earned her bachelor’s degree in political science and communications; a master’s in mass media and communications; and a juris doctorate. She told her parents she was going to be an attorney and a pop star when she was five-years-old. However, she knew her true destiny right before she started studying law in California. “My grandfather would always tell me you have to come back. You have to come back because you’re going to be able to take the company to the next level,” says Rolle.

Her family’s history alone makes the existence of Western Air virtually a miracle. Rolle’s grandfather worked on a mail boat and was a pastor with 13 children living on Andros, the largest island in The Bahamas. Rex and Shandrice had very little money growing up in Mastic Point, but a benefactor gave Rolle’s dad the money to go to flight school and become a pilot. “So many supernatural things have happened in regards to my dad’s life and my mom’s life. They are a walking testimony to miracles and the proof that anything can happen.”

Rolle spent most of her childhood going to school in America. She and her father were allowed to immigrate to the U.S while her mother attended college on a student visa. Rolle was around 10 when a trip home to Andros for the funeral of her great-grandmother became the inspiration for what would become Western Air. “We sat at the airport for hours upon hours upon hours. Being on the outer islands, we just weren’t a priority to the larger air carriers when they could be flying hundreds of people internationally.”

Photo: Western Air

Hearing so many people lament the time wasted waiting for delayed or canceled flights to outer islands made Rex and Shandrice want to buy a plane. They planned to start small, providing flights to Andros and Nassau for thousands of islanders inconvenienced by the lack of service. Another miraculous intervention came from the investor who decided they should get three planes with zero money down because he liked the Rolles and their idea. Western Air’s first flight in 2000 launched a family-owned business that is now worth millions of dollars. The airline has 16 planes, offering daily scheduled flights to Nassau, Freeport, Congo Town and Bimini and San Andros. There are also on-demand charter and private charters available for trips throughout the greater Bahamas and Caribbean, as well as Central and South America.

Rolle sees God in the breaks that contributed to her family’s good fortune, along with the hard work and dedication that she and her parents have put into building Western Air. “And that’s why especially now at this age, I pursue everything that I want to do. Whether it’s working or whatever new things I want to accomplish, I try it because I believe we can do it,” says Rolle.

That includes releasing “Here to Stay,” her first music video. The collaboration with Jamaican music producer Jevvo is a fusion of pop, reggae and dancehall. Rolle hopes people will accept her artistic side as simply another dimension of her personality. She plans to donate proceeds from sales of the song to the American Civil Liberties Union “to provide quality legal aid to immigrant families.” She feels it’s the right thing to do for people who have the same longing to succeed that she shared with her mother when they moved to America to get an education.

As vice president of operations, Rolle made consistent, on-time service and family-oriented customer service a hallmark of Western Air. Having conquered bureaucratic obstacles and other challenges in the past, she expects to find ways to overcome a pilot shortage to expand the airline. So, what is her vision for the future? “I would love to see us take on more international routes, which is the plan. I would love for us to be able to offer consistent air service between the Bahamas and Jamaica, the Bahamas and the Dominican Republic, and wherever we feel we can be of assistance.”

For now, Rolle is grateful for the loyalty of the airline’s 140 employees and many customers. She is also thankful that her family’s success story in an industry with few black-owned companies have the power to lift other people’s dreams. “I take that with great responsibility. I feel like what I have been able to do thus far is great, but there’s still so much to do and so much to improve upon and grow.”

Planning a trip to the Bahamas? Take a look at the services offered by Western Air by visiting Keep up with their routes and growth on Facebook.  You can also follow Rexy Rolle on Facebook where you can check out her video for “Here to Stay.”

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The joy of cooking became a part of her life when Phyllis was a child learning her way around the kitchen with her mother and grandmother. Her retirement from a demanding career in broadcast news has given her time to write about African-American chefs and restaurant owners as well as other black professionals succeeding in the travel and wine industries. Phyllis still loves to cook and try out new recipes.