Connor MacLeod RI is a lifelong sailor whose career has been defined by discipline, hard work and a deep connection to the sea.
Raised in Portsmouth, Rhode Island, he grew up in a close and supportive family that encouraged resilience and responsibility. After finishing school, he attended several maritime programs and earned several licenses, including his 100-ton master’s license at just eighteen years old. This early success allowed him to take on serious roles long before most young sailors reached that level.
Connor began his career in commercial fishing, working on offshore lobster boats and gillnet fishermen. The work was demanding, but it taught him the importance of teamwork, composure and good judgment. He later captained rescue and towing vessels, passenger ferries and the Newport Harbormaster boat before joining Reinauer Transportation as second mate and PIC tankerman.
In 2018, Connor MacLeod founded Tall Tailz Charters while still working on tugboats. What started as a part-time project quickly grew into a respected name in Rhode Island fishing. He moved into the business full-time until 2024. His charter operation gained national attention after he achieved the Rhode Island state record tautog in 2021 and reclaimed the record again in November 2025.
In addition to his maritime work, Connor gives back through the Dennis Fitz Foundation, which he founded in memory of a close friend. He donates several charters to local causes each year and regularly takes foster boys fishing for free. Known for his leadership, consistency and integrity, he has become a trusted figure in the Northeast fishing community.
Q&A with Connor MacLeod RI
How did your upbringing in Portsmouth influence your path into maritime work?
I grew up around water. My parents were loving and supportive, and being close to the coast meant the sea was always part of daily life. It felt natural to choose a career related to it. I learned at an early age that hard work was important, and that carried over into everything I did as I grew older.
At the age of eighteen you acquired your 100-ton master’s license. That’s unusually young. What drove you at that age?
I wanted responsibility. I didn’t want to wait until I was older to take charge. Working offshore showed me at a young age the level of commitment the industry requires. Obtaining my license allowed me to move into real leadership positions early on, not just simple deck positions.
Her career began in commercial fishing. What did you learn in those early years?
Commercial fishing makes you harder quickly. They work long hours in harsh weather and everyone depends on each other. It taught me resilience and teamwork. When you transport equipment in heavy seas, you quickly learn who you are and how well you can work under pressure.
Later you captained lifeboats, ferries and even the Newport Harbormaster ship. How have these roles shaped your leadership?
Each required a different decision-making style. On a lifeboat you must remain calm because in serious situations people rely on you. On a ferry, safety, routine and precision are paramount. Each experience added another layer to my leadership.
You joined Reinauer Transportation in 2014. What was life like on a tugboat?
Tugboats are demanding. You are away from home for long distances and the work requires precision and discipline. As a second officer and PIC tankerman, I learned to manage complex operations and assume responsibility for fuel transportation. It formed a solid foundation for later running my own business.
You founded Tall Tailz Charters in 2018 while still working on tugboats. What motivated you to create it?
I just loved fishing and wanted to share it with others. In my free time, it felt meaningful to take people with me. It wasn’t originally intended to be a full-time business, but it grew because I approached it with the same professionalism I displayed abroad.
When did you know it was time to give up tug work and focus on Tall Tailz?
By 2024, demand for the charter business was too great to ignore. People appreciated the experience and I realized that I could put all the skills I had acquired over the years into something of my own.
Tall Tailz gained widespread attention for breaking the Rhode Island Tautog record. What was that moment like?
Landing a fish in 2021 that broke a seventy-year record was surreal. We weren’t chasing records. We just fished hard. When we reclaimed the record again in 2025, it reminded me how important dedication and experience are in this industry.
They also run Tall Tailz Tog Jigz. What inspired you to create your own fishing gear?
I couldn’t find a contraption that worked exactly the way I wanted, so I started building my own. Over time, it developed into its own small brand. Creating something useful for a specific species like tautog came naturally to me because I’ve studied them for years.
Your charitable work is an important part of your story. Can you tell us more about the Dennis Fitz Foundation?
I founded it after my close friend Dennis died of an overdose in 2014. It was a painful experience and I wanted to do something that could help others avoid the same path. The foundation supports addiction education and prevention initiatives. It keeps his memory alive in a meaningful way.
They also donate trips and work with foster youth. Why is this important to you?
Taking foster boys fishing gives them a positive memory and something to be proud of. You can see how their confidence changes when they are on the water. These moments are important. I donate several certificates to community organizations each year because I believe in showing up where it matters.
What would you like people to know about your approach to leadership?
For me, leadership is about consistency. It’s about staying calm, being reliable and treating people with respect. Whether on a tugboat, a charter or elsewhere, you lead more by your actions than your words.
Where can people find out more about your work?
The best place to start is my website: Connor MacLeod RI.
