Connor MacLeod of RI: A Career Built on Discipline, Leadership, and Life at Sea

Connor MacLeod RI is a lifelong mariner whose career has been shaped 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 programmes and earned multiple licences, including his 100-ton Master’s Licence at just eighteen. This early achievement allowed him to step into serious roles long before most young mariners reach that level.

Connor began his career in commercial fishing, working on offshore lobster boats and gillnetters. The work was demanding, but it taught him the importance of teamwork, composure, and sound judgment. He later captained rescue and tow vessels, passenger ferries, and the Newport Harbormaster boat before joining Reinauer Transportation as a Second Mate and PIC Tankerman.

In 2018, while still working on tugboats, Connor MacLeod founded Tall Tailz Charters. What began as a part-time project quickly grew into a respected name in Rhode Island fishing. By 2024, he transitioned into the business full-time. His charter operation gained national attention after landing the Rhode Island state-record tautog in 2021 and reclaiming the record again in November 2025.

Alongside his maritime work, Connor gives back through the Dennis Fitz Foundation, which he founded in memory of a close friend. He donates multiple charters to local causes each year and regularly takes foster boys fishing at no cost. Known for his leadership, steadiness, 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 near the coast meant the sea was always part of daily life. It felt natural to choose a career connected to it. I learned early on that hard work mattered, and that carried into everything I did as I got older.

You earned your 100-ton Master’s Licence at eighteen. 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 command. Working offshore at a young age showed me the level of commitment the industry demands. Getting my licence allowed me to step into real leadership roles early, not just basic deck positions.

Your career began in commercial fishing. What did those early years teach you?

Commercial fishing toughens you up fast. You work long hours in rough weather, and everyone depends on each other. It taught me resilience and teamwork. When you’re hauling gear in heavy seas, you learn quickly who you are and how well you can perform under pressure.

You later captained rescue boats, ferries, and even the Newport Harbormaster vessel. How did those roles shape your leadership?

Each one required a different style of decision-making. On a rescue boat, you must stay calm because people rely on you in serious situations. On a ferry, the focus is on safety, routine, and precision. Every experience added another layer to how I lead.

In 2014 you joined Reinauer Transportation. What was tugboat life like?

Tugboats are demanding. You’re away from home for long stretches, and the work requires accuracy and discipline. As a Second Mate and PIC Tankerman, I learned to manage complex operations and handle responsibility over fuel transport. It built a strong foundation for running my own business later.

You started Tall Tailz Charters in 2018 while still working on tugboats. What pushed you to create it?

I simply loved fishing and wanted to share it with others. On my off-time, taking people out felt meaningful. It wasn’t meant to become a full-time business at first, but it grew because I approached it with the same professionalism I used offshore.

When did you know it was time to leave tugboat work and focus on Tall Tailz full-time?

By 2024, the demand for the charter business was too strong to ignore. People valued the experience, and I realised I could put all the skills I’d built over the years into something of my own.

Tall Tailz gained major attention for breaking the Rhode Island tautog record. What was that moment like?

In 2021, landing a fish that broke a seventy-year record was surreal. We weren’t chasing records. We were simply fishing hard. When we reclaimed the record again in 2025, it reminded me how much dedication and experience matter in this line of work.

You also run Tall Tailz Tog Jigz. What inspired you to create your own fishing gear?

I couldn’t find a jig that performed exactly how I wanted, so I started making my own. Over time, it turned into its own small brand. Crafting something useful for a specific species like tautog came naturally because I’ve spent years targeting them.

Your charitable work is a major part of your story. Can you share more about the Dennis Fitz Foundation?

I founded it after my close friend Dennis passed away from an overdose in 2014. It was a painful experience, and I wanted to do something that might help others avoid the same path. The foundation supports addiction awareness and prevention initiatives. It keeps his memory alive in a meaningful way.

You also donate trips and work with foster boys. Why is that important to you?

Taking foster boys fishing gives them a positive memory and something to feel proud of. You can see their confidence change when they’re out on the water. Those moments matter. I donate multiple charters each year to community organisations because I believe in showing up where it counts.

What do you want people to know about your approach to leadership?

Leadership, to me, is about consistency. It’s about staying calm, being reliable, and treating people with respect. Whether on a tugboat, a charter, or anywhere else, you lead by your actions more than your words.