Flashback to early 2025 and the much-anticipated launch of Compass TV. Among the familiar faces making a return to live broadcasting in Cayman were some new ones; fresh talent snapped up following a nationwide search for the next generation of journalists and broadcasters. One of those was Raegan Rutty, Cayman’s first Olympic gymnast, mental health campaigner and at the time of writing, Miss Universe Cayman Islands.
Around the same time, local businessman and youth advocate Gary Rutty, was announced as the Parliamentary candidate for George Town South for the newly created Cayman Islands National Party, with his wife Angel spearheading his campaign for election. Here was a family with big ambitions
Naturally, Cayman Parent wanted to find out more. What does it take to become an Olympian? What is involved in raising high-achieving children? What would the future of Cayman look like under Gary Rutty's deputy leadership?
Sitting down with Gary, Angel and Raegan was a pleasure and an honour. We soon found the Ruttys to be warm, funny and down-to-earth. Epitomising ‘Caymankind’, their thoughtful words on family, and their tender relationship with our islands, were a joy to hear. And what started as an unexpected journey through one family’s 100 years of influence in the Cayman Islands became a conversation on parenting, ambition and dreams for the future; for the Ruttys and for Cayman.
100 Years of Influence
For over 100 years, the Ruttys have been making their mark on the Cayman Islands. Almost a century ago Gary’s grandfather, Aston Rutty, was a Senior Government Officer in Cayman Brac during the 1930s. He was influential in the aftermath of the hurricane of 1932 which killed 117 people out of Cayman Brac’s total population of 1,200. Aston Rutty took charge in the wake of the destruction, organising a relief response.
According to David Wells, writer of ‘A Brief History of the Cayman Islands’, the captain of the ship that brought aid to Cayman later commented, “Mr Rutty, the collector, appears to have taken charge ably, and has done well in a difficult situation. He has not spared himself, and was worn out with his exertions.” For his heroic efforts in coordinating the response to the devastating hurricane, Aston Rutty was appointed a Member of the British Empire (MBE) and his contribution to the Brac was marked by the naming of the Aston Rutty Civic Centre in his honour.
And it seems the Ruttys’ participation in politics did not end there. After attending college in Jamaica and then studying at the University of Florida, Gary’s own father, Burns, entered politics, becoming a Cabinet Minister in the Cayman Islands Government in the 1960s.
Burns Rutty was instrumental in the decision to maintain Cayman’s constitutional position as a Crown colony following Jamaica’s decision to break all ties with the United Kingdom in the early 1960s. Burns argued alongside his Christian Democratic Party colleagues, Ducan Merren and Willie Farrington, in Parliament that the road to self-government for Cayman lay in remaining with Britain rather than retaining its historic ties with the newly independent Jamaica.
Ten years later, Burns was once again involved in a monumental decision that continues to impact the country we live in today. In the late 1960s, Cayman faced the decision of whether to adopt the new Jamaican currency or the US dollar. The decision was a difficult one since adopting the US dollar would place Cayman outside of the sterling system. Mr Rutty successfully argued for Cayman to introduce its own dollar pegged to the US dollar, a decision that has served Cayman very well over the years.
The impression left by Gary’s family reaches far beyond politics. His great grandfather on his mother’s side was Captain Rayal Bodden who helped build some of George Town’s most recognisable and iconic landmarks; the Elmslie Memorial Church, the Peace Memorial by the Town Hall, the Post Office and the George Town Library, as well as building mine sweepers for the UK Royal Navy.
It is no understatement to say that the history of the Rutty family and that of the Cayman Islands are very much intertwined, with their legacy stamped on all corners of the Islands. And now, in 2025, with Gary newly elected as the MP for George Town South and Deputy Premier of the Cayman Islands, a new chapter begins for the Rutty family and their legacy looks set to continue.
Growing up in Cayman
Gary Rutty, commonly known as ‘Peanut’, grew up playing on Seven Mile Beach, back when there was plenty of sand and, quite literally, nothing else. Playing with his sister, cousins and friends, they would run up the beach from where the old Royal Palms is today to, what is now, the Hampton Inn, with only the seagrapes watching over them. Growing up in the 1970s there was no TV, no air con and childhood was spent outdoors with friends and family: “Everything was outdoors. We played outside, we played with the neighbours. We'd play football, we'd play with cars. We'd go build forts in the bush and in the woods and hang out.”
In 1977, Gary and his family moved to Frank Sound. He has now lived in the same house with his family for 48 years – an ‘Eastender’ through and through.
Everything was outdoors. We played outside, we played with the neighbours. We'd play football, we'd play with cars. We'd go build forts in the bush and in the woods and hang out
In 1987, a party of Texans visited Grand Cayman, and among them was Angel, a 17-year-old visiting on a diving holiday. After meeting at the old Holiday Inn on Seven Mile Beach on her first night in Cayman, Angel and Gary went on to spend the rest of her trip together. Over the years, Gary would visit Angel in Houston and Angel would take trips to Florida to visit Gary in college. She would also spend her summers in Cayman, working part-time in Caymania Freeport and Kirk Freeport. Eventually in 1989, Angel made the move to Cayman. Angel’s first job in Cayman was as the bookkeeper at Blockbuster Video, a job she held down while studying for a degree in International Finance at ICCI at night. The couple were married in March 1994 and welcomed their first child, Hannah, in 1997.
Family Life & Parenting
Gary and Angel went on to have two more children, Gannon and Raegan. Like many other families in Cayman, the week was taken up by long drives to and from school and after-school activities. Hannah did swimming, Gannon did tennis and Raegan did gymnastics. “It was a commitment”, Angel says, “we lived in East End and had to get out the door by 6.05am. The kids were getting dressed and doing homework in the car, and we would eat breakfast in town. After gymnastics in the evening we wouldn’t get home until it was dark, and it would be dinner in the tub!” And, as many families in the Cayman Islands can vouch, this is still a common theme.
That was the best thing about living in East End. They were stuck with me in the car, to school and back. I got to hear everything; what happened during the day at school and everything else, which was brilliant. I was talking to my children every day.
The Rutty’s remain a close-knit family, “My family means more than anything else”, says Gary. No doubt, their closeness can be traced back to their shared desire to create a loving and nurturing home for their children. “That was a common goal between Gary and I, we wanted to make sure we had a loving unit.”
As parents, raising children was always about teaching them to respect others and be kind: “Be respectful to everyone that you encounter. Because no matter where you go in life, if you don't have good manners and respect, you can only go so far”, says Gary. And this parenting philosophy paid off. “You don't even really realise it until they go off to school. And it was great when the first two went off to boarding school...even the gardener and the people who used to clean the dorms, they would come up to me and say how wonderful my kids were. Because they're the only ones that would actually acknowledge them, know them by name”, added Angel, proudly.
For the Rutty children, growing up meant working in the family business. For nearly 40 years, the Ruttys owned Burger King, and Gary and Angel’s children didn’t shy away from helping out! “They were taught responsibility at a very young age”, Angel says, “from 13 they had to work in the family business to learn the value of a dollar!” Raegan recalls how she once rang up a phone bill and was made to work it off in Burger King! “One thing about parenting”, Gary chimes in, “we’re solely responsible for these beautiful things that we created called children. I brought our children into this world to raise them, and to instil in them the values, morals and ethics that I was taught.”
When it comes to family traditions, the Ruttys have their staples. Being from Texas, Angel always celebrated Thanksgiving in her home. “It’s all family-oriented, without the stress of presents. It’s just about spending time together”, Angel explains. She recalls how when the children were in school, all the teachers knew that the Rutty kids wouldn’t be there on Thanksgiving; “And yes, on Friday I would send the teachers a plate of food!”
Weekends were spent out on a boat fishing, which became a hugely popular pastime within the Rutty family. In fact, it was Angel herself who devised the BK Big Fish fishing tournament, now an island institution and the biggest angling event in the Cayman Islands. Raegan notes how she bought her first computer by selling the first wahoo she ever caught!
Gary and Angel’s eldest daughter, Hannah, and her husband have recently returned to Cayman from Dallas to raise a family. After getting his Master’s degree in entrepreneurship, Gannon is now living in Cayman working in business analysis. And since early 2025, Raegan has become a fixture in the homes of many in Cayman as she began her role on Daybreak Weather for Compass TV. Of course, before this job, Raegan was known to many as Cayman’s first Olympic gymnast and reigning Miss Universe Cayman Islands. But what people may not know is that Raegan's story is one of determination, grit and resilience.
Raegan’s Childhood
We wanted to find out more about Raegan’s journey to athletic, pageantry and broadcasting success.
As a child, Raegan was very busy. School, gymnastics and fishing were just some of the things that kept her occupied. “There was always something happening. My schedule was always packed and I feel like I never had a day off.” This continued as she made her way through school, playing her part by working for the family business whilst also becoming a female boss in training...
As a child, Raegan would sell limeade on the side of the road, and as she grew up, she would work as a make-up artist for events across the island in her spare time. “She’s the ultimate entrepreneur”, Angel tells us, and Raegan herself explains, “I don’t want to scratch a card and get the money. I like the work and getting the reward from it”. When Raegan was just 13 years old, she jumped on the slime craze bandwagon and began making slime at home and selling it in the family’s gas station. “I took $100 dollars I earned from doing make up, I did cost of goods and an inventory, I made the logo in Canva, I made an Instagram page and it became the hottest selling item in the gas station!” She made $15,000 a year from slime!
Gymnastics & Journey to the Olympics
It became clear that if Raegan wanted to pursue a career in gymnastics then she would have to move overseas for training. Motions Unlimited had served her well but the infrastructure just did not exist locally for Raegan to make it to the bigtime. “It was such a small programme in Cayman, and she needed more exposure”, Angel explains. During 8th Grade, Raegan and her mum took the leap into professional gymnastics, with mother and daughter flip flopping between Dallas and Cayman for training.
After six months, Angel moved back to Cayman and Raegan started living with host families in Houston as she worked toward her gymnastics dream.
Unfortunately, Raegan’s time in Houston wasn’t always easy. Feeling uncared for by host families and struggling with an antagonistic coach, Raegan began to question her decision. “Going to Houston made me kind of resent gymnastics because it made me leave my home, my family”, she explains. “I was getting abused by my gym coach and I just thought, ‘why am I doing this to myself?’”
Despite the verbal and emotional abuse, and not feeling respected by her coach, Raegan’s driving force became her focus on the 2020 Olympic games: “I knew that when 2020 came, if I was at the Olympics, I was going to succeed. That was always the goal.” In the lead up to the Olympics, Raegan had the opportunity to compete all over the world. Competitions started in the UK but then went on to include Namibia, Qatar and South America. In fact, Raegan has travelled to every continent except Antarctica during her gymnastics competitions! And her mum was always by her side at every competition. Raegan competed at the Pan American Championships, Commonwealth Games, Central American and Caribbean Games, World Championships, and finally the Olympic Games.
Tokyo Olympics 2020
Of course, 2020 was defined by the COVID-19 pandemic which led to global social and economic disruption that resulted in the postponement of the 2020 Olympic Games in Tokyo. When 2021 finally rolled around, Raegan had had an extra year to prepare for the games.
On June 28th 2021, Raegan received the Tripartite Invitation, an Olympic berth allocated to countries with less than eight athletes across disciplines at the previous two Olympic Games. With tears in her eyes, Raegan tells us how it was like a golden buzzer moment. After years of training, injury knockbacks and difficult coaches, her dream came true. “I thought back to that memory of when I was 15 asking, ‘why am I doing this to myself?’. It was suddenly all worth it.”
Raegan’s journey to the Olympics is evidence of her tenacious work ethic. Her entrepreneurial spirit, the sacrifices she had to make, and the unwavering commitment to her dream are just some of the reasons for her incredible achievements.
Thankful for being able to leave Cayman for gymnastics and school, Raegan attributes her personal growth to the time she spent away from Cayman. “It completely changed my life”, she says. “It makes you realise how blessed we are in Cayman. How fortunate that we live in such a close-knit community. We’re spoiled in Cayman; we’re safe and sheltered. But I also think leaving Cayman taught me who Raegan Rutty was and really made me develop a sense of independence.”
Raegan recommends that should the opportunity arise for anyone to leave Cayman for school, college, university, or any other experience, they should grab it with both hands!
After Tokyo
With the Olympics behind her, Raegan followed in her grandfather’s footsteps, attending the University of Florida. There she studied Psychology, a pursuit driven by both her experience with an abusive coach and being bullied during her childhood. Her studies led to an internship at an advocacy centre, where Raegan worked with abused children.
Having struggled in the past with her own mental ill-health, she found she was turning off the empathy switch a little too much in her personal life and, after graduating, she decided she wasn’t going to grad school and returned to Cayman.
Miss Cayman was always a dream of Raegan’s and in 2024 Raegan competed, winning the title of Miss Universe Cayman Islands. Inspired by her own journey with mental health, and seeing friends suffer, Raegan dedicated much of her reign to helping promote social change surrounding mental health and suicide awareness, focusing on breaking the stigma of these issues in Cayman.
And it is perhaps in her mental health advocacy work that Raegan has had the greatest impact in her career so far. She has toured schools and sports clubs, contributed on the panels of mental health conferences, participated in mental health charity events, and sat in the studios of every local radio station to advocate for better mental health support for young people.
In doing so, Raegan started a podcast, The Raegan Way, in which she talks about gratitude, mindfulness and her own difficult journey with her mental health. “I was an elite gymnast, and I wasn't allowed to cry”, Raegan says. “I wasn’t allowed to show emotions. At that time it was not okay to not be okay.” Having come through the other side of a difficult battle with her own mental ill-health, Raegan’s goal for her podcast was to show people that it is, in fact, okay not to be okay. To show people that, as Raegan says, "Life is tough and it’s going to suck sometimes, but you can, and will, overcome it." By sharing her personal journey on the podcast, Raegan hopes that the youth of Cayman will know that though they may not be feeling good in this moment, this feeling too shall pass. In a world where many young people are struggling with the ups and downs of daily life, Raegan’s message of compassion but also of resilience is very powerful. “I really wanted to just be there for people, as the internet's big sister”, Raegan says.
A New Generation of Legacy
Having closed the door on her gymnastics career and with her reign as Miss Universe Cayman Islands ended, we wanted to find out what the future holds for Raegan Rutty.
“I think it’s important for people to realise that being Miss Cayman is more than a crown and sash", Raegan tells us. "You will be Miss Cayman forever, but your reign won’t last forever, and so you have to be okay with just being yourself first.” Raegan recognises that a crown and sash don’t define her, and she’s ready to hand over the crown to the next queen and continue chasing new dreams for herself.
You will be Miss Cayman forever, but your reign won’t last forever, and so you have to be okay with just being yourself first.
Focusing on her new career in broadcasting, Raegan is excited for her future at Compass TV. Growing up being interviewed during the Olympics and her pageantry career, Raegan always wondered what it would be like to be the person in the chair opposite her; asking the questions rather than answering them. So when the opportunity arose to work in TV, Raegan couldn’t believe her luck.
Now, happy at Compass TV, Raegan’s big dream is to have her own show, interviewing people from all over the world, “Just like Jimmy Fallon, fun and entertaining, with a focus on human stories!”
Of course, we wanted to know whether the Cayman Islands can expect Raegan to follow her family footsteps into government. “I really love Cayman. I'm a proud Caymanian and I would love to help make Cayman a better place. So sure, I would do politics.” We may just see Raegan Rutty in Government yet!
A New Generation of Politics
Some in the community might have been surprised in early 2025 when Gary Rutty was announced as the Cayman Islands National Party election candidate for George Town South. Gary had retired from many of his business ventures and was enjoying spending time with his family and being out on his boat. In the April election, not only did Gary win his seat but he was also made Deputy Premier of the Cayman Islands. We wanted to know what drove Gary Rutty out of retirement and into government.
Firstly, Gary recognises the hard work and lasting impact of his forefathers on the Islands. “To have built what we have here today is very special”, Gary notes, “and I don’t see the opportunities I was given being given to our children today.” Supporting youth development in Cayman, Gary has been involved with the YMCA organisation, Cayman Islands Little League and more. He hopes his political legacy will be most keenly felt by the next generation of Caymanians. He wants to give back to the same community that gifted him opportunities in the past. “Our children must be prioritised, and we must provide a platform and an education system for all Caymanians to thrive. For everybody to thrive.”
Our children must be prioritised, and we must provide a platform and an education system for all Caymanians to thrive. For everybody to thrive.
For families, Gary believes that the cost of living and quality of life are the two major issues facing parents today. Discussing the biggest issues facing families, Gary fervently says that “communication is key”, highlighting the issues of young people’s unrestricted access to technology and having so much outside influence. “That was the best thing about living in East End”, Angel explains. “They were stuck with me in the car, to school and back. I got to hear everything; what happened during the day at school and everything else, which was brilliant. I was talking to my children every day.”
Tenacity, Family, Legacy
In wanting to find out about what it takes to raise an Olympian, we uncovered a family whose forefathers have influenced the story of Cayman, a mother whose presence in her children’s lives was instrumental to their success, and a daughter whose steadfast willpower and Olympic dream helped propel her into the record books.
Our conversation with Gary, Angel and Raegan Rutty was filled with warm-hearted laughter and celebrated their family history and ties to the Cayman Islands. As Gary Rutty begins his journey as Deputy Premier of the Cayman Islands and his daughter, Raegan, continues down her broadcasting path, the legacy of the Rutty family is sure to be continued…
