Bill Pinkney, left, poses with a family at the Jackson Park Yacht Club in Chicago, Ill. in 2023. A former Navy sailor, Pinkney battled storms, dehydration, sleep deprivation and loneliness while sailing alone around the world, becoming the first Black sailor to do so by way of a treacherous route around Cape Horn. He died Aug. 31.

Bill Pinkney, left, poses with a family at the Jackson Park Yacht Club in Chicago, Ill. in 2023. A former Navy sailor, Pinkney battled storms, dehydration, sleep deprivation and loneliness while sailing alone around the world, becoming the first Black sailor to do so by way of a treacherous route around Cape Horn. He died Aug. 31. (X, formerly known as Twitter)

Bill Pinkney, who battled storms, dehydration, sleep deprivation and loneliness while sailing alone around the world, becoming the first Black sailor to do so by way of a treacherous route around Cape Horn, died Aug. 31 at a hospital in Atlanta. He was 87.

His death, during a visit to Georgia from his home in Puerto Rico, was confirmed by Chicago restaurateur Ina Pinkney, his former wife. She said he had suffered “catastrophic” injuries in a recent fall.

Pinkney set sail from the Boston Navy Yard with little fanfare on Aug. 5, 1990, giving three blasts from his horn and placing a call to Ina, his wife at the time, back home in Chicago. “It’s a good day,” he said. “I’m going sailing.”

That was an understatement. Pinkney had spent years planning the journey, which ended 22 months and 27,000 miles later, on June 9, 1992, when he became one of only a few Americans to have circumnavigated the globe solo. It was an epic feat of single-handed sailing, all the more remarkable because he had chosen the most difficult route, passing under the five southernmost capes instead of traveling along the globe’s center, via the Panama and Suez canals.

The day he rounded South America’s Cape Horn - “the big daddy,” as he called it, out of respect to a hazardous route that sailors have likened to Mount Everest - he popped open a bottle of champagne and, following an old sailing tradition, put a gold earring in his left ear.

By then he had faced a barrage of obstacles while captaining his nine-sail, 47-foot cutter, the Commitment. There were engine troubles and autopilot failures, then a pair of hurricanes that threatened to crush him from opposite sides near Bermuda. An emotional arrival in Cape Town, where he first encountered the continent of his ancestors (“It was like I was standing outside myself, watching a movie”), was followed by near-disaster in the Indian Ocean, where his boat was twice knocked over by wind and waves.

While far from shore, Pinkney subsisted on canned goods, crackers and prepared meals from Hormel (he regretted not bringing more candy) and typically slept no more than six hours a night. In quiet moments he would pass the time by reading, working through a library of paperbacks that ranged from Shakespeare to Danielle Steele. The solitude took its toll, and when conditions permitted he would use a satellite phone to call his wife.

“Ina,” she recalled him saying, “there are some stories I can tell other sailors. There are some stories I can tell other solo sailors. And then there are some stories I can never tell.”

Pinkney’s progress was followed by thousands of schoolchildren in Chicago, his hometown, and in Boston, where he had obtained funding for the voyage from a real estate investment firm. A natural storyteller with a talent for connecting with children, he made video lessons for students that he mailed home at port, according to Ina, and wrote a book for first-graders, “Captain Bill Pinkney’s Journey.”

Some of his footage was used for an educational program - “The Incredible Voyage of Bill Pinkney,” narrated by TV star and comedian Bill Cosby, a friend from his Navy days - that won a Peabody Award.

“I wanted to do something to leave as a legacy to my grandchildren,” Pinkney told an interviewer, explaining his motivations for the voyage. “And I said, ‘Well I can’t leave them money, but I can leave them a benchmark to follow.’”

The lead-up to the trip was an odyssey in itself. Pinkney, a former cosmetics executive, was working as an official in Chicago’s Department of Human Services when he was laid off in 1984. Growing up on the city’s South Side, he had been enchanted by “Call It Courage,” a children’s book by Armstrong Perry about a boy who overcomes his fear of the water through a journey at sea. Now, he decided, it was time for an adventure of his own.

Pinkney had learned to sail small skiffs in the Navy, taken more advanced lessons on City Island in the Bronx and began sailing solo in Chicago, where he bought his first boat in the late 1970s and grew tired of waiting around for friends to join him on the water. He initially planned to circumnavigate the globe through the canal route, which Teddy Seymour took in 1986 and ‘87 while becoming the first Black man to sail solo around the world.

But through his friend Cosby, he met industrialist Armand Hammer, who offered up $25,000 in seed money and urged Pinkney to travel to London for a visit with Robin Knox-Johnston, a British sailor who had completed the first solo nonstop circumnavigation in 1969.

“If you go through the canals, nobody will remember that you did this,” Knox-Johnston told him, according to an account in the Chicago Tribune. “You might as well go around the five capes - the right way.”

Pinkney took his advice. To fund the journey, he spent two years pitching corporations on the trip, presenting the voyage as a potential marketing coup. By his estimate, he received 300 rejections, including from his former employer, Johnson Products.

After a short article on his plans ran in the New York Times in 1989, he found a key backer in investor Todd Johnson. The MacArthur Foundation signed on as well, as Pinkney expanded the educational components of the trip, meeting with scores of schools across Chicago and helping to develop history and geography lessons for students who would track his journey while sticking pins in classroom maps.

The voyage was far from his last trip at sea. Upon his return, weary but still in good spirits, he recommitted himself to blue-water sailing, saying that he considered “the real world” to be one in which a 50-foot wave was breaking behind his boat, not one in which he worried about mortgage payments and credit card bills.

While serving on the board of the Mystic Seaport Museum in Connecticut in 1999, he led a six-month educational voyage to re-create the Middle Passage of the Atlantic slave trade, taking teachers and students to Puerto Rico and Brazil and then on to Ghana and Senegal. The next year, he began captaining the museum’s replica of the Amistad, a cargo ship on which West African captives rebelled in 1839, seizing control of the ship and, in a case that was dramatized in the Steven Spielberg film “Amistad,” winning their freedom.

Pinkney would lecture about the history of sailing while often answering questions about his own journey around the world. Ina Pinkney recalled that upon his return home, “somebody said to him, ‘What was the most courageous thing you did out there? And Bill said, ‘Untying the boat to leave. All the rest is just staying alive.’”

The older of two children, William Deltoris Pinkney III was born in Chicago on Sept. 15, 1935. His parents divorced when he was 6, and he and his sister were raised by their mother, who worked as a maid.

The family received public assistance at times, and Pinkney came to feel like an outsider as one of only four Black students in his graduating class at Tilden Technical High School. He spent much of his free time in the Museum of Science and Industry, reading exhibition placards, and dreamed of becoming an artist, an idea that his mother dismissed with a quip: “The only people who make money in art are dead White men.”

Around the time he entered high school, he experienced a spiritual crisis, Ina Pinkney said. “His mother would go to storefront churches, and Bill would go with her. Then one day he said to her, ‘I can’t go with you anymore. Every time I go, they say when you die, everything is great. You’ve got to go to heaven before everything is good. Why can’t it be good here?’ “

At his mother’s urging, he went to the library, checked out a book on comparative religion and read it cover to cover. He decided he would become Jewish, and began going to temple before converting as an adult.

After graduating high school, Pinkney trained as an X-ray technician and served in the Navy as a hospital corpsman. In a 2006 memoir, “As Long As It Takes,” he recalled that after he was discharged he abandoned his first wife, Yvonne Glover, and their young daughter, moving to Puerto Rico and leaving them behind on the mainland.

“I still feel ashamed and diminished by it,” he wrote, “and I don’t like to talk about it. . . . I ran then, and in some ways I am still running.”

Pinkney worked as a bartender, elevator mechanic, limbo dancer and newspaper stringer before relocating to New York City, where he resumed his X-ray work. He married Ina in 1965 and, around that same time, became a makeup artist, working on commercials, magazine shoots and low-budget movies. He once did makeup for a horse, painting a stripe down the middle of its face for a western.

In 1973, he joined Revlon, working on marketing for a Black cosmetics line. He moved to Chicago four years later after being recruited to launch a line of high-end cosmetics for Johnson Products.

Pinkney’s marriage to Ina ended in divorce in 2001, although the two remained close. He married Migdalia Vachier in 2003, and together they moved to Puerto Rico, running a charter boat business out of the city of Fajardo. She survives him, as does his daughter, Angela Walton; his sister; and his two grandchildren, to whom he dedicated his voyage.

In 2021, Pinkney was inducted into the National Sailing Hall of Fame. He was the first Black sailor to receive the honor, although he downplayed that achievement, telling PBS NewsHour that the sea was “a great equalizer.”

“The sea doesn’t care what your economic status is, your religion, your nationality, your sex. It doesn’t care what you think. It cares about one thing,” he continued: “I am the sea.”

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