When Charlie Enright first jumped on a boat at Oakcliff Sailing in Oyster Bay in 2011, no one might have guessed that in less than 15 years he would become CEO of US Sailing.
Enright, a prominent figure in the sailing world, with a decorated history at Oakcliff and beyond, was announced as the new head of the nation’s governing body of sailing on April 14.
His journey from young sailor to leading the most prestigious sailing organization in the United States reflects his deep-rooted passion and commitment to the sport, as well as the lessons he learned sailing in Oyster Bay.
Enright, 40, a native of Bristol, Rhode Island, made clear his enthusiasm for his new role, emphasizing his lifelong connection to sailing. He learned to sail at age 5, he said, and had been on the water for years before that with his family.
“Sailing has always been in my DNA,” he said in a recent interview. “I grew up right here in Bristol, where my grandfather was a boat builder. I started sailing at a young age, and from there it became a lifelong pursuit.”
Enright sailed competitively throughout his childhood and teenage years, and at Brown University he was a team captain, won numerous awards and led his team to top-five finishes at the College Sailing Team Race National Championships in 2004 and 2008.
His path to the leadership of US Sailing began with his involvement in the Oakcliff All American Offshore Team in 2011, where he played a pivotal role in shaping offshore sailing initiatives.
He had come to Oakcliff with a group of sailors after they filming their participation in the Transpacific Yacht Race for a Disney documentary called “Morning Light.”
Enright and the group, which had set their sights on winning an around-the-world race, decided to train at Oakcliff, a premier sailing and training center. Dawn Riley, director of Oakcliff Sailing, highlighted Enright’s early contributions.
“Charlie was always one of the leaders on the team, and he and his college roommate, Mark Towill, were the real power of the organization,” Riley recalled. “Once you graduate from Oakcliff, unless you really screw up, you’re always a graduate.”
Enright’s tenure at Oakcliff marked a significant period of growth and achievement for the organization. While there, he helped form the Oakcliff All American Offshore Team, which raced in major international races like the Transpacific and the Rolex Fastnet Race.
“Oakcliff provided invaluable opportunities for hands-on learning and development,” Enright said. “I firmly believe in learning through doing, and Oakcliff’s philosophy aligns perfectly with that.”
He had his greatest success in 2023, when he and the 11th Hour Racing Team, which he co-founded, became the first Americans to win the Ocean Race, across Europe.
In his new role, Enright aims to leverage his experience to advance US Sailing’s mission and impact. “Becoming the CEO of US Sailing is a milestone for me personally and professionally,” he said. “I see it as an opportunity to give back to the sport that has given me so much.”
US Sailing, founded in 1897 in Enright’s hometown of Bristol, offers training and education programs for instructors and race officials, supports sailing organizations and communities, and generally helps to support the growth of the sport.
“US Sailing has been around for a long time before me, and hopefully will be around long after me,” he said, so his focus is on supporting the sport and the people who love it, rather than making big waves.
“My approach will be to observe, assess and then implement strategic improvements,” Enright explained. “We aim to enhance membership engagement, generate revenue, and foster collaboration within the sailing community.”
Riley emphasized her friend’s readiness for the role. “He is young and pumped up to take on this new challenge,” she said. “He’s looking forward to the challenge, and you have to do that, because there is going to be some challenging days ahead.”
Enright is optimistic about the future of sailing in the United States. “US Sailing has a longstanding legacy, and my goal is to build upon that foundation,” he said. “We will work closely with partners like Oakcliff to strengthen our programs and initiatives, ensuring that we meet the needs of our members and the broader sailing community.”
For more information about Oakcliff Sailing, visit its website, OakcliffSailing.org.
