A Captain Shaped by the Sea
Some people grow into their careers. Others grow up inside them. Connor MacLeod falls into the second group. His story is not a quick rise or a lucky break. It is a steady climb built on discipline, skill, and a deep respect for the ocean he works on every day.
“I’ve spent my whole life on the water,” he said. “It’s where I learned who I am, and it’s where I built my career.”
Today, Connor is known across Rhode Island and the Northeast fishing community as the owner and operator of Tall Tailz Charters. But his path to becoming a trusted leader in his field started long before he launched his business. It began in Portsmouth, Rhode Island, with supportive parents, strong family ties, and a childhood shaped by the coastline.
Early Experiences That Built a Mariner
Connor’s introduction to maritime work wasn’t casual. After graduating high school, he went straight into professional training. He attended several maritime schools and earned the licenses and certifications needed to work offshore. At only 18, he reached a major milestone when he earned his 100-ton Master’s License.
“I wanted to take on responsibility early,” he said. “Getting my license at 18 let me step into real roles, not just deckhand jobs.”
He began his career on offshore lobster boats and offshore gillnetters. These were not easy jobs. The hours were long, the work was physical, and the conditions were unpredictable. But they taught him how to operate under pressure and handle challenges with a level head.
“That time in commercial fishing shaped everything that came after,” Connor said. “It taught me resilience and what it means to work as a team when conditions are tough.”
From Commercial Fishing to Commanding Vessels
With his early experience behind him, Connor advanced quickly through the maritime world. He captained a rescue and tow boat, small passenger ferries, and the Newport Harbormaster vessel. Each role expanded his leadership skills and deepened his understanding of the responsibility that comes with being a captain.
In 2014, he joined Reinauer Transportation, a respected tugboat company, where he served as a Second Mate and PIC Tankerman. Tugboat work demanded precision, discipline, and long stretches away from home. But it also gave him a broader understanding of maritime operations and fuel transport logistics.
“I loved tugboat work,” he said. “But I also knew I wanted to build something of my own.”
That idea eventually became the seed for Tall Tailz Charters.
Starting Tall Tailz Charters While Working Offshore
In 2018, while still working full-time on tugboats, Connor launched Tall Tailz Charters as a part-time business. He wanted to share his love of fishing with others and create experiences that reflected the professionalism he brought to all his maritime roles.
“I started it on my off time,” he said. “It wasn’t meant to be a big business at first. I just wanted to take people fishing and do it the right way.”
Over the next few years, the charter gained momentum. Clients appreciated his skill, calm leadership, and ability to teach even the newest anglers how to fish with confidence. As word spread, the demand grew.
Stepping Into Entrepreneurship Full-Time
By 2024, Connor made a major decision. He retired from tugboats and committed himself full-time to Tall Tailz Charters. It was a leap, but one backed by years of preparation and a strong reputation in the fishing community.
The business quickly became recognized for its professionalism and consistent results. In 2021, it earned statewide attention after landing the Rhode Island state-record tautog — a record that had stood untouched for 70 years.
“It was surreal,” Connor recalled. “We weren’t chasing a record. We were just fishing hard. But when it happened, it changed everything.”
Though the record was broken again in 2024, Tall Tailz reclaimed the title on November 9, 2025.
A Captain Who Shows Up for His Community
Connor’s leadership extends beyond the wheelhouse.
In 2014, after losing his close friend Dennis Fitzgerald to an overdose, he created the Dennis Fitz Foundation to support addiction and drug-prevention programs. He donates six to seven charters a year to local fundraisers and often takes groups of foster boys fishing at no cost.
“These trips matter,” he said. “Fishing can give kids a sense of pride and freedom. Sometimes it’s the first positive memory they’ve had in a while.”
Building Tools for Other Anglers
Connor’s innovation doesn’t stop with charter work. He also founded Tall Tailz Tog Jigz, creating one-of-a-kind fishing jigs designed for tautog — a species he has become widely known for.
“It started because I couldn’t find a jig that did exactly what I wanted,” he said. “So I made my own.”
Where His Career Stands Today
Connor is more than a charter captain. He is a respected figure in Rhode Island’s fishing world, a published author in several fishing magazines, and a seminar speaker for the Rhode Island Saltwater Anglers Association.
His career shows what can happen when experience, passion, and discipline compound over time. It also shows the power of building a business not for hype, but for service.
As Connor puts it: “Everything I do comes back to the same idea — work hard, treat people right, and respect the ocean.”
Learn more about him at Connor MacLeod RI.
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