Old Salt: Captain Brad Simonds A Florida Keys Legend

From Ivy League to Open Seas: Captain Brad Simonds’ Journey

Not everyone lands their dream job straight out of college. Yet, that’s what happened to Captain Brad Simonds. Five months after getting his Ivy League sheepskin from Princeton University, Brad scored his first professional mate’s job on the 48-foot Ding Dong II out of Islamorada, Florida, working for Capt. Ray Merrill. “Needless to say, I wasn’t the most popular kid in my family at that point,” said Simonds, who majored in American History, and wrote his senior thesis on the Magnuson Act and what it meant to the New England Groundfishing industry.

His father, a prominent Boston attorney, had hoped his son would follow in his footsteps, but Brad took a different route. “I had a friend named Rob Kilgore, who sold advertising for Florida Sportsman,” Simonds said. “His beat was the Florida Keys. Once a month he’d drive the Keys, hit all the marinas, and re-up the ads. When he got to Bud n’ Mary’s, he started talking with the owner, Richard Stanczyk. Rob said something like, ‘I got this kid living in my house and he’s gung-ho to go fishing. Have you got a position?’ and Richard said, ‘Send him down, we’ll put him to work.’ That was my introduction to Bud n’ Mary’s and the start of my career.”

Decades of Dedication: Captain Simonds’ Lifelong Sportfishing Career

Forty-four years later, Brad is still fishing. He’s the owner-operator of Southpaw Fishing Charters, running his custom 43-foot Torres sportfisherman, Southpaw, out of the Oceans Edge Resort & Marina in Key West. He’s one of the legendary captains to earn the sport’s highest accolade, the Tommy Gifford Award by the International Game Fish Association (IGFA). From then to now, it’s been a hell of a ride.

New England Beginnings: Brad’s Early Fishing Adventures

Brad grew up in Carlisle, Massachusetts, a Boston suburb. His early memories are of angling for smallmouth bass and pickerel on nearby freshwater lakes and ponds. His father took him up to Maine in the summer, and the two would fish for trout.  Brad’s saltwater fishing introduction came via his grandparents, who had retired to a waterfront home on Buzzard’s Bay. “I remember being a kid at my grandparents’ place and it was fish, fish, fish all the time,” he said. “I must have been a pain in the ass.They were all sailors, but all I wanted to do was wet a line. I was probably six or seven years old then. I enjoyed fishing from then on.”

A Fortuitous Encounter: Starting a Career in Sportfishing

Tautog, a wrasse species native to the Western Atlantic, was the saltwater fish that obsessed Brad most as a child. “I didn’t have anybody at that age that knew anything, so I was on my own trying to figure out how to catch it,” Simonds said. “Garden worms. Clams. I finally hit on crabs later on.”

Memorable Moments: A Swordfish Battle to Remember

The whopper influence on Brad’s fishing happened when he was a teenager. A friend of a family friend knew Frank Mather, the Woods Hole Oceanographic Institute scientist who founded the Atlantic Cooperative Game Fish Tagging Program. Mather said he was looking for a kid to help him on his boat in the summer, and Brad fell into the job. His best fishing story with Mather occurred in the 1970s.The two cast off from Woods Hole on Frank’s 26-foot Hydra-Sport and headed to an area called the “dumping ground” off Nomans Land. They spotted three or four fishing boats and thought they’d try their luck.

“We hadn’t had a chance to rig any natural baits on the way out, so we stuck a couple of the early Frank Johnson Mold Craft Little Hooker lures out on 30-pound outfits,” Simonds said. “Kaboom. It went off! I grabbed the rod and remember Frank in my ear saying, ‘Goddamn rod grabber.’ He was a classic curmudgeon. I probably should have deferred to him, but I just jumped in. We fought this fish for a little while. He pulled drag and we got him back. It was a darn 300-pound swordfish that we hooked on a lure. It happens, but it’s rare. We fought it for two-and-a-half to three hours. Every time we got him close, and it looked like we could gaff him, he turned back towards the boat, and we had to keep him away from the outboards. This went on and on. Finally, we broke him off. The snap swivel had failed. The swivel was still there, and the one end of the snap was still there, but it had busted at the bottom of the snap. Just fatigued. We lost our swordfish. It was a great battle and a heck of a story. I’ve gotten over it 50 years later, but at the time, it was crushing.”

Navigating New Waters: The Keys and Beyond

Mather had a winter home on Key Biscayne, where he maintained lab privileges and an office at the University of Miami. Simonds often visited. It was on a spring trip to Walker’s Cay with Frank aboard his 28-foot Bertram, Ahi, that Brad caught his first marlin. It was a 200-pounder caught while trolling off a long rigger baited with a bonefish. Mather introduced Simonds to Kilgore.

“I got to Bud n’ Mary’s, and wow, it was surrounded by fishing people,” Simonds said. “Islamorada was a hotbed.  I would see Ted Williams at the post office. Jimmy Albright was on the dock, so was Cecil Keith and Alex Adler. All these legendary characters, all these fish heads. It was a whirlwind. I was just trying to absorb it all. The competitiveness of it all.”

Simonds had worked for Merrill on the Ding Dong II for about three to four months when he received an offer he couldn’t refuse. That was, to jump ship and work on a private boat, the 53-foot Hatteras, Quintana Roo, helmed by Capt. Frank Kessell, that was headed to Cozumel. Simonds couldn’t think of anything more exotic. Off they went, albeit dead reckoning with no navigational aids. The boat’s Loran had broken, and in a rush, the owner promised to ship them one once they reached Mexico. One day out, Quintana Roo ran up on the Colorados Reef, off Western Cuba.

“We were high and dry at 2 a.m.,” Simonds said. “The Cuban authorities came out, but they couldn’t reach us since we were in only about two feet of water. We jumped off and swam to the Cuban boat and they brought us ashore. We got interrogated for a couple of days, then they took us to Havana. There was no U.S. Embassy at the time.  A woman with the Swiss Embassy found us, took care of us, and finally got us out after about 10 days. The boat was a loss. We were all fired by the owner when we got back to Miami.”

Simonds went back to Bud n’ Mary’s with his tail between his legs and Merrill re-hired him. Six months later, he went to work with Capt. Dietmar Kossman, first on The Destiny, then for private owners on a 57-foot Billy Holton called the Keowee. In 1984, Kossman quit, and Simonds took over the captain’s chair, having received his captain’s license the year before. They spent the summer at Pirate’s Cove in Oregon Inlet, then down to Key Largo in the fall, where Simonds began chartering out of the Ocean Reef Club.

“My deal with the private owners I worked for was straightforward,” he said. “I always told them ‘If you don’t allow me to charter, I won’t work for you.’ The reason is that I had spent too much time watching private boat guys go through all the rigamarole to take a boat to an exotic location and then sit there because the owners were too busy, too distracted to come fish, and guys would miss a whole season.  A lot of guys wouldn’t hire me for that reason, but so be it.”

Simonds’ private captain career spanned a dozen years, from his start on the Keowee in 1984, to driving Final Fantasy, a 54-foot Bertram. These were his traveling years, too. At the height, the year started in the winter in the Keys, then to Isla Mujeres in the spring for sails. In 1987, Simonds tagged and released 155 sailfish to win the species trophy as part of the Southeast Fisheries Center’s Oceanic Pelagic Programs. He ranked among the top five captains from 1985 to 1990 in the Cooperative Tagging program, which Mather began. It later became the AFTCO Tag/Flag Awards, for which Brad was named Atlantic Ocean Captain of the Year in 1994 and 1995. But back in 1987, he was captaining Larry Liebert’s Miss Guided. That year was the first he took the 54 Bertram to St. Thomas. The destination became a circuit regular during the summer to early fall.

Champion of the Blue Marlin: Innovations and Achievements

“We pulled into a slip on “A” dock in Red Hook, got squared away, and walked the dock,” Simonds said. “We were so excited to be in the blue marlin Mecca, and then everyone said they were not biting. We had charters coming up and had to figure out where the North Drop was before that. We were really in the dark. Literally too. The dark of the moon as well. So out we go, up and down the edge. We weren’t sure where we were, but I’ll be damned, they were biting. The only other boat out there was OB O’Bryan, on the Knightlines. OB calls later that afternoon and says, ‘I saw you stop a lot. What kind of a day did you have?’ I told him I was 5 for 9. Can you imagine? I didn’t even know where I was going. That day set me up for the rest of my career. Because from then on, I was confident. I caught 28 blue marlin in my first week of fishing in St. Thomas, four a day. I was successful from then on.”

Simonds never caught 100 blue marlin in a St. Thomas season as many people did, because he’d head to Venezuela in September or October, two moons that can produce big numbers. Still, in 1996, Brad released 248 blue marlin from June to November between St. Thomas and Venezuela.

Pitch-bait fishing proved a big reason for his success. It’s a technique Simonds introduced to St. Thomas, starting on his boat in the 1989 and 1990 seasons.

“I was by disposition a dead bait, not lure, fisherman,” he said. “But in St. Thomas, I wasn’t seeing as many fish in a day as the guys who were torquing around at high speed with lures. I was seeing four, they were seeing eight. It was frustrating. I thought, ‘How am I going to find a way to see more fish, to go faster, and yet still feed these fish a natural bait rather than just cross my fingers and hope it hangs on if it piles on a lure?’ That was the evolution of it. We found that we were raising lots of fish because we were going fast, plus we had a great catch ratio because we were feeding them a natural bait. We were pitch baiting full-time for two or three years before the rest of the fleet caught on.” In St. Thomas in 2015, Simonds was inducted into the USVI Open/Atlantic Blue Marlin Tournament’s Board of Captain’s Hall of Fame.

From Private Ventures to Public Charters: The Southpaw Legacy

Tex Schramm’s 53 Hatteras, Key Venture, and Dan Doyle Sr.’s 53 Hatteras, Blank Check, were two other programs Simonds ran during his Atlantic traveling days. He says he got along well with some owners, and tolerated others. At the end of the day, he wanted to be his own boss. So in 2002, he went to Key West and had the renowned Claude Torres build him a boat. No bells and whistles, just simple and dependable. That’s the Southpaw.

“I enjoy the challenge of taking people’s money and then finding a way to make them satisfied,” Simonds said. It’s the basic nuts and bolts, he adds, of figuring out how to catch fish given the day’s conditions. He has some 40 rods on board and is prepared to do different things during the day – live baiting, anchoring, trolling, to get a catch and make clients happy. But day chartering isn’t without its excitement.  A decade ago, Brad took first-time clients offshore the first week of June to catch dolphin.

“We’re trolling and pretty soon there’s a blue marlin bite,” he said.  “We catch it, and it’s a run-of-the-mill fish, about 125 to 130 pounds. The big deal is that we don’t get many blue marlin bites in Key West. So, the next year, he charters me again for the same date. Here we go, and during the day, here comes a blue marlin again. The guy releases the fish, looks up at me, and says, ‘Man, you guys have blue marlin here!’ I tell him, ‘Sir, that is the first and only blue marlin we’ve caught since the one you caught a year ago.’ I told him he needed to play the lottery next.”

Vision for the Future: Brad Simonds’ Fishing Bucket List

First-time trips to Baja California’s Magdalena Bay and Africa’s Cape Verde and a return to fish Australia’s Great Barrier Reef are still on Brad’s bucket list. As he says, “I’m more interested in catching a big blue marlin than catching 50 sails.” About the IGFA’s Tommy Gifford Award Brad says, “I’m humbled and honored. Like I said at the start of our conversation, I didn’t know anyone was paying attention. I’ve just been going along doing my thing. But it’s a wonderful accolade.  You look at the people who’ve been honored and it’s a ‘Who’s Who’ of the industry.”

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