Bill Pinkney: A Singular Sailor

It’s about a two-block bike ride from Bill Pinkney’s house in Fajardo, Puerto Rico, to the marina where a 44-foot Norseman catamaran is moored. He knows the boat well. Until the pandemic crushed the charter boat industry last year, he and his wife, Migdalia, led charters aboard it for a Chicago-based partner. Now, Pinkney is “a boat nanny” instead. The pandemic also crushed the partner’s business, so he sold the boat, and Pinkney is looking after it for the new owner. “That’s the way it goes—first your money, then your clothes,” Pinkney laughs ruefully.

It is that quick, wise sense of humor about the vagaries of boats and life that makes Pinkney seem 85 years young. (Nor does it hurt that the former professional limbo dancer can still cut a serious rug.) It’s also a trait that helped him become the first African American to solo circumnavigate via the five capes, along the way inspiring tens of thousands of youngsters to think outside of any boxes society placed them in.

When he sailed his Valiant 47 Commitment into Cape Town, South Africa, he was one in a line of countless sailors over generations who had done the same. What set him apart was the way he did it.

The year was 1990. Just 10 months earlier, Nelson Mandela had been freed from Robben Island after 27 years of imprisonment. Apartheid was still in place, despite growing international pressure to end it. The country was a tinderbox of unrest, anger and tension.

Pinkney could have slipped across Table Bay just as the handful of racing sailors completing leg one of that year’s BOC Challenge had done weeks before. But the time, the place and the wind were right, and the sailor was ready. He raised his red, black and green spinnaker. “These were the colors African Americans displayed as a banner in our struggle for freedom from second-class citizenship and discrimination,” Pinkney writes in his memoir As Long as it Takes. “I wanted all to see who I was and where I came from.”

As he approached Robben Island, another boat came to greet him, this one skippered by South African sailor Neal Petersen, whom Pinkney had befriended while Petersen was in the U.S. drumming up support for his own effort to become the first Black person to solo circumnavigate nonstop. (Pinkney stopped in five ports, some more than once, on his journey.)

“I had gone through what you were going through, with segregation in the U.S., and now I’m coming to South Africa, where that same system is in play,” Pinkney said in an interview with Petersen years later. “And for both of us to be standing on our dreams and to say to the whole world, ‘Hey, we can make it, this whole thing on both sides is ridiculous,’ it was a very important statement to make.”

It was also a bold statement to make in that place and time, but Pinkney is nothing if not intrepid, willing to push himself to live outside others’ perceived boundaries in order to achieve his goals. To categorize him—as a Black sailor, an adventurer, a ground-breaker—is to circumscribe someone who has consistently defied such narrow definition.

After his 32,000-mile circumnavigation ended in June 1992—an accomplishment that was read into the Congressional Record and became the subject of a Peabody Award-winning documentary—Pinkney got involved in another exceptional project, Mystic Seaport’s construction of Amistad. He also became the first captain of the schooner, a replica of the ship on which an 1839 revolt by would-be slaves sailing from Cuba became the first case of its kind to go before the U.S. Supreme Court. In 2010, Pinkney was aboard when Amistad sailed into Havana, Cuba, under the U.S., Cuban and U.N. flags in recognition of the U.N.’s International Day of Remembrance of the Victims of Slavery and the Transatlantic Slave Trade.

A nominee to the National Sailing Hall of Fame, Pinkney as yet has not been inducted. “He did a helluva thing,” says Mark Schrader, who in 1983 became the first American to solo circumnavigate via the five capes and went on to sail Lone Star—which Pinkney purchased for his journey and renamed Commitment—in the 1986-87 BOC Challenge. “It wasn’t easy, but he just kept at it. And he did it with a sense of humor.”

“My friend Bill Pinkney and his cohort, Paul Mixon, are some of sailing’s real heroes,” Peter Johnstone, founder and former president of the multihull company Gunboat International, wrote in a 2007 letter to Scuttlebutt. “These guys have a dream and they simply do it. It is pure love of life and sailing, an inspiration for all.”

The circuitous route that led Pinkney into the history books began on Chicago’s South Side, where he grew up under the careful wing of his single mother. She worked as a domestic and instilled in her son an adaptability he would rely upon to navigate as a young Black man in America. 

“She taught us rules of etiquette,” Pinkney says. “When the phone rang at our house and my mother answered it I could tell who she was talking to by how she spoke. If she was talking to someone who was white or in authority, her English was impeccable. No slang, no accent, impeccable. When she talked to one of her sisters or friends, it was jargon, slang and everything else. Understanding how to function, where you need to function. That showed me that adaptability was survivability. If you don’t adapt, you won’t survive. Had I not had that ability in a lot of situations, I would not have been successful.”

In the 2019 New York Times story “The Perfect Divorce,” Pinkney’s second wife, Ina—a gregarious, white, Jewish woman whom he married against her parents’ wishes in 1965—summed up this trait perfectly. “Bill has self-preservation in his DNA. He knows how to relate to any person anywhere, and though he was often the only Black man in the room, he is comfortable everywhere.”

Pinkney wasn’t an avid student, but he was a voracious bookworm, and in seventh grade he read Call It Courage by Armstrong Sperry, the story of a young Polynesian boy who overcomes isolation and ostracism by embarking on a hero’s journey at sea. It resonated deeply with Pinkney, who was struggling with feeling like an outcast in school. He would sit on the shore of Lake Michigan “and ponder what was on the other side. It wasn’t until much later in life that I put those two things together; wanting to see the water, wanting to have a great adventure, and putting them together in the form of sailing.”

During high school, Pinkney joined the Naval Reserve. After he graduated in 1954, he embarked on eight years of active duty. After being discharged, he returned to Puerto Rico, where he’d been stationed for a time, and got his first real sailing experience on the small inter-island boats that moved goods down island.

“That was a such a joy. I was so fascinated by these guys who had a little compass and three lanterns—red, green and white—and that was it. And they’d take off at night and end up the next morning in St. Thomas or St. Croix,” he says. “They were excellent sailors, and the sails were made up of just about everything you could think of. They had more patchwork on them than a patchwork quilt. The boats had a little cuddy, but primarily they were using all the space to carry cinder blocks, Coca-Colas, sometimes refrigerators and stoves that people had purchased at Sears in Puerto Rico. They used the space very judiciously. If you wanted a nap, you found a space on deck where you could just curl up.”

Eventually, Pinkney returned to New York City, where he moved to the East Village and cast about for his future course. It was here that he met and married Ina and began working as a make-up artist, which would lead him to a career in the beauty industry, specializing in products for African American women. He joined Revlon in 1973, becoming the company’s first Black marketing executive. When he took a job with another company in Chicago in the late 1970s, he began sailing and racing on Lake Michigan and purchased his first boat—a Pearson Triton he called Assagai, a Berber word describing a short, jabbing spear. “I have a picture of it on my desk. I loved that boat,” he says.

By 1985, approaching the age of 50 and sick of corporate life, Pinkney’s youthful dream of adventure beckoned. He conceived the idea of solo circumnavigating, using the experience to inspire his two grandchildren. But what began as a fairly modest idea morphed into something much grander. By the time Pinkney began his voyage on Commitment, he’d be recording videos and communicating via single sideband with some 30,000 students in Chicago and Boston schools. “I wanted to prove to kids with backgrounds similar to mine, especially Black males, that they didn’t have to give in to statistics that they were likely to do drugs, die in a gang fight, or end up in jail,” he writes in As Long as It Takes. “They could be successful if they persevered.”

While using sailing as a vehicle for traditional school subjects, he also focused his unique lens on aspects of culture in the stopover ports that he believed would intrigue students at home. In Salvador de Bahia, Brazil, for instance, he described the influence of African slaves on the city’s music and culture while filming capoeira—a hybrid martial arts-based dance form that originated among enslaved people. “I want to show my students at home how many of their fads like breakdancing had roots somewhere else,” he says in the documentary.

Todd Johnson, a longtime sailor who led the Boston-based group Combos that largely funded Pinkney’s voyage and who also was his primary contact and weather assist over its duration, says Pinkney’s desire to inspire young people—both during and after the trip—was key.

“Kids got something out of this, and it wasn’t math, science or geography. It was knowing that Bill, who had been born into a difficult situation on the South Side of Chicago, had made something of himself,” Johnson says. “When Bill came back to Boston, there were about 5,000 kids waiting for him on the dock.”

Pinkney’s journey was a repeated lesson in adaptability. He had set off with relatively little offshore ocean experience and virtually no solo passagemaking aboard Commitment. Though he was methodical and conservative, sailing across any ocean—and especially through the Southern Ocean and around Cape Horn—is never without risk and trial. 

“Every time you go sailing, you learn something new about sailing, the weather, the boat and yourself, because you’re challenged,” he says. One of the worst times, he says, was after leaving Hobart, Tasmania, bound for Cape Horn, and coming down with what he believes was the flu.

“I thought we had lost him overboard,” says Johnson, who was tracking Pinkney via Argos transmitter. “I knew Bill was extremely cautious about staying tethered all the time, but there was just no communication for three days and combined with the plot that was just unbelievably erratic, we were really concerned.”

Pinkney says he had recorded two videos to be shown to the students if he was lost at sea. Mindful of how Christa McAuliffe’s death in the Challenger disaster had traumatized students who were following her, he wanted to be sure they knew the risk he had taken was one he had accepted knowingly. “I knew the dangers involved in following my dream, and I asked them to continue following theirs and never give up.”

After completing his circumnavigation, touring countless schools, helping develop the documentary of his voyage, and writing a children’s book, Pinkney in 1994 joined the board of Mystic Seaport, where his work with Amistad began. He also founded the Middle Passage Institute, a project to enable teachers to sail to Africa and develop curricula about the effects of the trans-Atlantic slave trade. He also joined the board of the American Sail Training Association. He remains an overseer with SEA, the Sea Education Association.

Next year will mark 30 years since he finished his circumnavigation. 

“There are days I would love to be transported right back out there again,” he says. But, along with a bucket-list item of being at the Formula One Grand Prix, he’d settle for a trans-Atlantic from the Med to Barbados or St. Lucia. “That’s downwind all the way. Christmas sleigh ride,” he muses. “And I’d like to do it in a big multihull, like a Gunboat 66. Downwind with that baby? Whoa. Put up a code zero and boogie.”

This article was originally published in the July 2021 issue of our sister magazine Soundings.