Captain Teddy Seymour and Captain Bill Pinkney both passed away in 2023 leaving a legacy that should be welcome applause to a point in history that sees too much conflict and division, writes H.E. Ross.

Their legacy could be said to be without a chance: they became the first African Americans to have sailed around the world single-handed.

Why emphasise African American in place of just sailor? Good question that I hope to answer in this article.

“I started sailing in Puerto Rico and I loved it from the start,” Captain Bill Pinkney nods and continues, “I think it’s the independence of it. In sailing, you have absolute sovereignty. You have an opportunity to at least temporarily capture nature and bend it to your will. I say temporarily because nature changes. The sea’s calm and then it’s stormy. When you think you’ve mastered it, it masters you.”

If you met the very affable Bill Pinkney on the street or while trying to talk you into supporting one of his projects, you’d not think of him as a humble man.

Bill Pinkney has used his sailing experiences to inspire young people. Credit: Octane Rich Media/Yeva Dashevsky/James Forni/Chicago Maritime Museum

At 80, he shared a Facebook post showing off his cha-cha moves. No, the one-time limbo exhibitionist and Revlon executive would not be the one facing the wall at a party.

But Pinkney was also dedicated to paving the way for children to be confident and not shy to get aboard sailing boats the way he was when he was young.

Of course, building a dinghy and having to be rescued might have influenced the safety part of his push to get children into a real grasp of freedom offered by sailing, and away from the grasp of the street.

For his circumnavigation, Pinkney chose a cutter-rigged Valiant 47, named appropriately Lone Star.

Why did he choose this particular design and sail plan? The cutter rig of the Valiant provided a variety of sail options without too much handling on the deck.

With contributions from many, including the investment firm Alrich, Eastman & Waltch, he was able to purchase the Valiant 47.

This particular boat had solid offshore credentials; the boat had previously been sailed successfully and without much hardship by Captain Mark Schrader in the 1986-7 BOC Challenge.

Capt Bill Pinkney wrote a children’s book about his circumnavigation just a few years before he died. Credit: Bill Pinkney/Chicago Maritime Museum

With the vision of owning this boat the direction of his project changed.

“I was going to sail around with a 32ft boat, go through the Panama and Suez Canals and write to my grandchildren to tell them not only about where I was and what I was doing, but how I was using all of the things that I learned in the first 12 years of education.”

But using his mantra, ‘Never let a chance go by.’ he changed the concept, bought Lone Star, renamed her Commitment, changed rigging and equipment where needed and sailed 27,000 in a little less than a year and a half alone.

He was 55, with very little experience of sailing long distances alone, having mostly raced as crew or solo aboard his 28ft Pearson Triton in Lake Michigan.

His scheduled stops were at Salvador, Brazil, Cape Town in South Africa (where he memorably sailed past Nelson Mandela’s island prison of Robben Island, flying a spinnaker of red, black and green (the colours African Americans displayed in their struggle for freedom from second-class citizenship and discrimination), Hobart, Tasmania, and Punta del Este in Uruguay.

With further acumen, Pinkney moved the original concept to a greater one by giving sponsorship talks with the idea of then transmitting a daily passage report to 30,000 children.

At each stop, he’d send videotaped messages home to his wife, Ina, and the school children of Chicago and Boston; 700 students were on the dock at the Charlestown Navy Yard to greet him as he tied up Commitment behind the USS Constitution on his return.

“The streets do offer a need for self-reliance and observance of ever-changing situations. I found that the youth who were court referrals grasped the concept of change faster than those I taught who did not have that need in everyday life.”

Capt Bill Pinkney was the captain of the replica of La Amistad for two years, sailing the ship to Europe, Africa and the Caribbean. Credit: Associated Press/Alamy

Bill Pinkney was a man who came from the streets, with the single parent and poverty background that many see as destined to end only one way, but he went another way that showed alternatives that he was open to throughout his life.

‘Never let a chance go by’ helped him sail around the five southernmost capes to tie up where he’d cast off.

Then he went on to get sponsorships for his Middle Passage Project voyages to Africa, South America and the US to form an African studies curriculum for teachers who made the voyages.

His crowning achievement was to be the first skipper aboard the era-replicated Amistad and to meld that representation of a successful slave mutiny into a Middle Passage Project voyage under the auspices of the Mystic Seaport Museum. (The original ship, La Amistad, was seized by the authorities after Mende captives took control of the ship in Cuba and tried to sail it back to Africa. The subsequent court case became the first human rights case in the US Supreme Court, which was won by the Mende.)

Captain Pinkney emphasised the freedom aspect of the sailing world, “… that’s the identity that all of us who sail want. Religion, sexuality, colour, none of that has anything to do with the fact that, first and foremost, we’re sailors.”

Unfortunately, written maritime history usually emphasises European maritime history.

We, up to this moment, still have to say Black maritime history to include what is being scantily researched about our involvement on the water.

Going back through time, Black mariner, Captain Alexander Leidesdorf sailed his schooner (with a crew) from New York to the village of Yerba Buena and after setting up trade routes between Mexico, Hawaii, Alaska and this little village he had the name officially changed back to the Spanish Mission name of San Francisco de Assisi.

Captain Leidesdorf is buried at Mission Dolores. Assisting the first successful slave revolt in Haiti was the first Black officer in the British Royal Navy, Captain John ‘Jack Punch’ Perkins who captured over 300 ships during his service.

The first back-to-Africa movement was accomplished by the Horatio Alger-type Captain Paul Cuffe who took them to Sierra Leone aboard one of his 11 ships.

Cuffe traded and whaled along the coast of Africa, the Mediterranean, the Baltic and even the slave-owning states in the newly founded United States of America.

The first six books written about the enslavement experience in America were written by Black mariners who understood and appreciated the concept of freedom.

Teddy Seymour spent less than $6,000 during his 16-month voyage, and supplemented his stores of rice and beans with fish. Credit: Maya Gates-Seymour

Though Teddy Seymour had a similar upbringing to Bill Pinkney, with his mother making sacrifices to ensure that her four children had just enough, Teddy had a more racially traumatic upbringing during his ghetto school years.

Luckily, he saw that one spark that changed his world when his principal assigned him to athletics and his coach mentored him in such a way that he became a cross-country track star.

This earned young Teddy a scholarship, and with that acceptance and celebration by his college peers that in turn made him a happy student.

In 1965, Teddy Seymour joined the Marines and became an officer, as he held a diploma.

Eventually retiring from the Marines seven years later, he’d completed a tour in Vietnam, and was the 31st Black captain in the history of the Marine Corps, the oldest branch of services in the United States.

He started sailing with the Marines around Camp Pendleton in Southern California.

Teddy Seymour spent 11 years modifying Love Song for solo sailing before his 1986-87 single-handed circumnavigation around the world via the Panama and Suez Canals. Credit: Maya Gates-Seymour

After learning in a couple of dinghies he bought a Columbia 26 and lived aboard for his last two years in the Corps.

He then bought his Love Song, a Bruce King-Carl Alberg designed, Ericson 35 Mk1.

He took off and sailed down to Panama and across the Caribbean Basin to the US Virgin Islands where he taught in a primary school.

He then decided to sail around the world.

According to his sister, Ruth, Teddy described himself as someone who takes risks and overcomes challenges to accomplish a goal. “He didn’t start out with the dream of sailing solo,” she said. “He just wanted to sail.”

Teddy Seymour learned to sail in the US Marine Corps before buying his Ericson 35 Mk1. Credit: Maya Gates-Seymour

That is shown in his serious detailing and planning for a voyage that would happen seven years later. During those seven years, he accumulated most of the funds through saving and keeping his life simple.

“A major decision was made during the summer of 1985, to become departure-date oriented. After the February 1986 departure date was set, the level of motivation reached zenith, and preparation activity heightened during several busy months.” Captain Seymour’s boat was generally sound as proven by his voyage from San Diego to the US Virgins.

“My Ericson 35 is a solid, full keel boat. During 11 years of ownership, she has been heavily reinforced, modified, and equipped for solo cruising. The running rig was altered for the purpose of safety and convenience. Sails are hoisted by halyards tended from the cockpit. Lowering sails is also accomplished from the cockpit by pulling lines led to the head of the sails.

“The mainsail is held on the boom by lazy jacks, and the jib is held on the deck by a net connected to the forward stanchions. This method reduces the possibility of being thrown overboard in a rough sea, and the displeasure of getting wet while working the foredeck. All new 5/16in stainless steel stays were installed, with the addition of double headstays.

“Having a mast stepped on deck requires a strong support system to transfer the force, exerted through the mast, to the keel; The tabernacle was dismantled and rebuilt with heavy timbers. The mast head was strengthened. Two previous collisions with logs off the coast of Central America, suffering no damage, has given me confidence in hull strength. Nevertheless, the bow has been fortified with six layers of 24oz mat and epoxy resin,” he explained.

“The purchase of sails, ground tackle, satellite navigation, solar panels, refrigeration, and a ham radio, helped deplete the money saved during the past seven years of working two jobs, seven days per week.

“By departure date, the cruising budget diminished from $12,000 to $6,000. How can a world cruise be accomplished with a boatload of provisions and $6,000? Only five stops are planned, and money will only be spent on essentials. That’s my no-frills circumnavigation of the world.”

Teddy Seymour spent 50 years living and sailing on Love Song. Credit: Maya Gates-Seymour

In the end, Teddy Seymour made 12 stops on his voyage, which took him via the Panama and Suez Canals to the likes of Bora Bora, Australia, Yemen, Israel and Egypt before returning to Frederiksted, St Croix, US Virgin Islands.

His 16-month circumnavigation was uneventful in terms of groundings and knockdowns, which he put down to his gear and planning.

He was later honoured by the likes of the Joshua Slocum Society and the Cruising Club of America but otherwise received little mention in the press apart from in a few sailing magazines, and returned to his job teaching and living on Love Song.

• Capt Teddy Seymour, born on 1 October 1941, and died on April 11, 2023 – The first Black man to circumnavigate the world solo, sailing from 24 February 1986 to 19 June 1987.
• Capt Bill Pinkney, born on 15 September, 1935, and died on 31 August 2023 – The first Black man to circumnavigate the world solo via the five southernmost capes, accomplished from 5 August 1990 to 9 June 1992.

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