TARPON SPRINGS — The boat was 32 feet, white fiberglass, with sails stretching up, up, up. It was, Carl Shepherd decided that day, the boat he would retire in.
"What are you going to do?" asked his friend, Michael Ellzey, who drove him to Fort Myers in August to check out the vessel.
Sail everywhere, Shepherd told him. Live out the rest of his life on the water.
But Shepherd didn't get to spend his last years peacefully on a sailboat. Instead, he spent his final moments in chaos on a shrimp trawler in the middle of one of the most powerful hurricanes in recent history.
Shepherd, 71, went down with the boat — called the Capt. Eddie — during Hurricane Irma. So did the vessel's cat, Motorboat. The only one who made it out alive was the captain, Edward Potter, for whom Shepherd was working as a deckhand.
It would mark the end of a long, eventful life for Shepherd, who migrated to the United States decades ago from his home country of Guyana along the north South American coast. He spent much of his life on the water, using his knack for fishing he learned growing up. On the mainland, he was a regular at the library, a volunteer for a local nonprofit, a friend to many in Tarpon Springs.
"It could have been worse," Ellzey, 57, said of the hurricane. "But I lost my friend."
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Shepherd was born July 4, 1946, at Georgetown Hospital in Guyana. He and his twin brother, Cary, were the first sons of what would become a large family: 10 children, all raised by their late mother, Myrtle. The eldest brothers went to work early to help with the family finances, the youngest sibling, Stanislaus Shepherd, said. Their uncle, a fisherman, taught them his craft.
"Life was difficult," the youngest brother said. "We didn't have much, but we had lots of love."
In the 1970s, Shepherd migrated to the United States. He left behind five children, whom he later reconnected with, and their mother, his children said.
He lived in a few places before settling in Tarpon Springs. There, he made a name for himself as a reliable deck hand who, despite his age, worked harder than the young workers.
"He would ask for nothing," said Rick Shalansky, a shrimp boat captain for Pelican Point Seafood. "He just wanted to smell the world down here."
But when it came time for a wedding or church, the deck hand left behind his white rubber boots for sleek suits with pocket squares or patterned button-downs with crisp white pants. From Shepherd's home, a rental near the Sponge Docks with a front stoop home to many conversations and cups of coffee, Ellzey hung onto two things: a wooden figurine of a shrimp trawler and a white fedora with a red and black feather on the side.
When Shepherd wasn't hanging out with Ellzey or at the docks, he volunteered at the Shepherd Center, a local social services nonprofit, or went to the library. He went from having no computer skills to researching ocean currents and weather forecasts on the Internet. Salvatore Miranda, a librarian, said the staff helped him make his own email address a couple years ago. He picked a name many in town knew him by: fishermancarl.
He'd use it to communicate with his daughter Carlotta Austin in Barbados and check in on his other children in Pennsylvania and New York. They had reconnected in the 1990s, his daughter Dilicia Spencer said.
Ellzey guessed the library computers are where Shepherd found the ad for the sail boat. It was on the drive to look at it that Shepherd got a call from Potter saying he wanted to go out for a fishing trip. The men often worked together and had become close friends.
They left a few days later. With the devastation from Hurricane Harvey still playing out, Ellzey felt funny about the trip. But he didn't share his feelings with his friend.
He would come to regret his silence.
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As Hurricane Irma grew more powerful in the Atlantic, Shepherd's family started to get nervous.
The boat's destination was about 40 miles south of Fort Jefferson, about 70 miles west of Key West. In Pennsylvania, Spencer spoke with him via satellite phone. They were anchored and safe, he said. He'd see her at a family reunion planned for Sept. 23.
But Irma chugged farther and farther west. The next contact came the Sunday the storm swept through the Florida Keys. Shepherd called his sister, Wendy Rudder.
"Sis, the boat is sinking. The boat is sinking," he said, according to Rudder.
"If you don't hear from me again," he told her, "tell everyone I love them."
That was the last time she talked to him.
The family would learn that Potter had made it onto the life raft but Shepherd had not. The Coast Guard deployed a helicopter and an airplane out of Alabama to attempt a rescue, but a Carnival cruise ship on its way to the Bahamas was closer. The crew picked up Potter just after 10 p.m. The trawler — and Shepherd — were nowhere in sight, said Coast Guard spokesman Lt. Cmdr. Ryan Kelley.
When he arrived back in Tampa, Potter told reporters it had been "a trying few days." He could not be reached for further comment. The Coast Guard is investigating Shepherd's death, Kelley said.
Potter's wife notified friends in Tarpon Springs of his death, but family members were left wondering what happened. Almost five days after the phone call with Rudder, Austin's boyfriend found an article online about the fateful journey.
"I couldn't speak anymore," Austin, 46, recalled when she found out. "I just started screaming."
For now, family and friends chalk up what happened to a series of bad decisions and miscalculations. Other boats, including the one Shalanksy captains, went in days before the storm hit.
After his death, Carl Shepherd's two worlds converged. Ellzey showed Stanislaus Shepherd, Austin and Spencer around the town where their father and brother had made such an impression. The reactions and stories stuck with them.
"He shared his life with others and made other people a little better," Austin said.
During an interview this week, Ellzey tried to imagine what his friend might be up to if he had returned. Maybe riding his bike around passing out shrimp from his catch. Maybe on the phone with his children and brothers and sisters. Maybe on his big white sailboat, beginning his retirement at sea.
Senior researcher Caryn Baird contributed to this report. Contact Kathryn Varn at (727) 893-8913 or email@example.com. Follow @kathrynvarn.