Flashback 1994: Man Who Sailed Around World Looks Toward His Next Journey

     In Sunday's post about Paul Vallas, I mention Bill and Ina Pinkney, both profiled years ago. I'm posting Bill's today, and Ina's on Thursday.  This is a long piece, 1900 words. The paper used to do that sort of thing. But if you soldier on until the end, I'll give an update on what Bill is up to today.

What happens to a dream deferred?
Does it dry up
like a raisin in the sun? . . .
Maybe it just sags
like a heavy load.
Or does it explode?
         — Langston Hughes, 1951

     Bill Pinkney does not lead a life of quiet desperation. He does not race with the rats. His nose is not to the grindstone. His dream, undeferred, did not dry up like a raisin in the sun.
     Pinkney wanted to sail around the world, and did so, two years ago, becoming the third American — and the first African American — to make the trip solo while rounding all five major Southern capes.
     But the story does not end there. At age 59, Bill Pinkney says he is just warming up. He sees new challenges, like distant sails on the horizon, approaching in his future.
     "I could never be the person I was before I left," says Pinkney, dapper in a black silk shirt, new jeans and tasseled loafers. "No way. Never. People say, `Oh, Bill, how are you doing now that you're back in the real world?' No, no, I left the real world to come here. This is not real - " he gestures to his near West Side loft, with its shelves of books and walls of awards. "This is manufactured. . ."
     While he is looking ahead, the nearly two years he spent circumnavigating the globe are still very fresh with him.
     "I'll give you an example of real," he continues. "A 50-foot wave breaking behind your boat. There is nothing more real than that, not your mortgage payment, not whether or not your American Express bill is paid. That's not real."
     Captain Pinkney — the title is not an honorific, but refers to his Merchant Marine 100-ton captain's license — relives his adventure, in motivational speeches before groups ranging from major corporations to public school classrooms. He has written an illustrated children's book, Captain Bill Pinkney's Journey and a $39.98 video, narrated by Bill Cosby, has just been released.
     The bare facts of his journey have the power to amaze. He covered 27,000 nautical miles over 22 months, 16 of which were spent at sea, alone, aboard a 47-foot yacht. He faced 50 mile-per-hour winds and 30-foot waves. Yet, with hindsight, he views the journey as a peaceful, almost boring time.
     "Seventy-five percent of the voyage was quite enjoyable and rather uneventful," he says, pointing out that half the battle was careful attention to preparation and a sailor's caution. "Most of the time when you hear of great disasters, it's because the expedition was planned and executed poorly. Rarely do experienced seamen really get caught in bad conditions."
     But friends say that Pinkney is just being modest.
     "If you know anything about sailing, it's a hellish, hellish proposition," says fellow sailor Morris Bleckman. "There's one leg (of the round-the-world trip) about 61 days, by himself. It's not for the fainthearted. Single-handed sailing demands more from anybody else than any other sport. You depend entirely on your own wits and your own guts and nothing else."
     Asked anything he would do differently, Pinkney mentions trifles — having; a refrigerator would have been nice. But as far as his own performance, he surprised even himself.
     "I found my capabilities were greater than I thought," he says. "You really never know these sort of things about yourself until you are pressed."
     Little of Pinkney's life would, at first glance, seem to have pointed him toward his epic journey. He grew up in the neighborhood of 33rd and Indiana, "what at that time was known as Bronzeville," he says, accenting the word in what sounds like contempt. "My father was a houseman, a male domestic. He and my mother got divorced when I was a small child."
     He grew up, at times on welfare, and graduated from Tilden Tech in 1954. Like so many adventurous young men, Pinkney went to sea with the Navy, where he worked as an x-ray technician. He loved it, served eight years, and might still be there today if it weren't for the racism common in the Navy.
     "The only reason I got out of the Navy is they wouldn't give me a commission," he says. "They weren't interested too much in giving blacks commissions in the 1950s."
     Back in civilian life, he worked at a variety of jobs — in a hospital, as a bartender, elevator repairman and limbo dancer in Puerto Rico, where he moved on a whim. Relocating to New York in the early 1960s, he decided he was tired of x-rays and trained as a makeup artist, working as a freelancer on commercials and movies. He met and married his wife and together they sailed remote-control sailboats on the pond in Central Park.
     Pinkney eventually moved into the corporate cosmetic business, launching brands aimed at African Americans, first for Revlon, then for Johnson Products.
     Revlon transferred him back to Chicago in 1974, where he hooked up with Flash Cab founder Arthur Dickholtz, who served as his sailing mentor.
     The idea of sailing around the world began to gel for Pinkney in the mid-1980s, as he set out on the daunting task of taking an indistinct dream and making it real.
     The assumption is that anyone who sails yachts must be a wealthy man. But Pinkney had only limited resources, and to make his dream real he first had to find corporate support. On his side were two lures: not only would the voyage generate publicity, but Pinkney devised an ambitious plan to involve thousands of schoolchildren in his journey, communicating with them via satellite and using his trip to teach math, geography, history and science. Still, it was a hard sell.
     "I had 30,000 kids every day for two years for $375,000 (the cost of the trip) — you couldn't buy them a piece of bubble gum on that kind of money," he said. "But an Anheuser-Busch, a Quaker Oats, couldn't see the value of that."
     Chicago educator Iva Carruthers helped Pinkney craft his proposal, though not without initial reservations.
     "I said, `Bill, you're absolutely crazy,' " remembers Carruthers, a professor at Northeastern Illinois University, who told him to meet her at her office at 8 a.m. the next Monday in the hopes that he wouldn't show up.
     "When I got in, he was already there, waiting for me," she says. "He started sharing with me his dream. It became clear to me that all he was asking me to do was write a proposal, and that if he was willing to risk giving up his life alone at sea, I could certainly do what comes easy to me."
     Industrialist Armand Hammer could, too, and contributed $25,000 in seed money. But full sponsorship was not forthcoming. Pinkney approached some 300 different companies over a period of two years. All rejected him. Particularly galling to Pinkney were rejections from two categories he thought should be eager to support him — black-owned corporations and the makers of marine products. In the end, the crucial money came from a Boston financier named Todd Johnson.
     Pinkney feels he was at a disadvantage because of the perception that black people aren't sailors. It is a thought that sends him hurrying to his bookshelves to refer to volumes documenting black seamen, flipping pages to show photos of ship's records listing black crews.
     "The assumption is . . . black people don't sail," he says. "Nothing is further from the truth. Look at the history of our country. We are a maritime nation, and (black people) have been part of the maritime history of this country from before it was a country."
     He set sail from Boston in August, 1990, and returned in June, 1992. The videotape of his adventure, which originated as a Peabody Award-winning special for the Discovery Channel, consists mostly of videos Pinkney shot himself, sometimes happy and invigorated, admiring fantastic sunsets, other times wet, sick and miserable, battened down below decks and outlining dire conditions while his sailing gear rocks back and forth in the huge swells.
     Included are scenes of eager classrooms tracking Pinkney on maps, talking to him through the roar of satellite static, or watching his "video postcards." (Pinkney, though cut off from all direct human contact for months at a time, manages pearls such as praise for the "wonderful sovereignty of being alone.")
     Still, the connection with schools was not a complete success, particularly in Chicago.
     "It didn't work out as well in Chicago as I would have liked it," says Pinkney. He says going through the Board of Education led to the mishandling of the Chicago end of his voyage, particularly when he got back.
     "I would do three schools a day," he says. "I'd get to the school and they didn't know who I was or why I was there. It was crazy."
     All that is going to be fixed in his next project — a journey, with crew this time, retracing the triangular slave route between Brazil, the Caribbean and West Africa. This time he hopes to involve a half-million students.
     This will take money, and Pinkney has already started the distasteful process. His first dollar was easy — ponied up by a Charleston chief quartermaster named Manning Harvey. Pinkney has the dollar pinned to the wall.
     "I'm well on my way," Pinkney laughs. "I only have 849,999 to go."
     So what does a man learn, alone in a boat, facing the boundless ocean, for the better part of two years?
     "The simple truths of life," he says. "When I was out there, there were no days of the week. Because I was alone, because my life functions around what I have to do to maintain it, the only place in the world that exists is right there. The old saying, `There is no tomorrow'? There is no five minutes from now. There's only now, and that's the thing, to take action.
     "This was a dream; this was not the dream," he says. "I wanted to leave a benchmark of achievement for my grandchildren. (Pinkney's only child, Angela Walton, 35, a daughter from his first marriage, lives in Florida with her husband and two children.) This showed me that you can make dreams come true. But I should be able to accomplish more. I've got a list I can't even get halfway through in my lifetime. I'm writing my book — an adult book, not about sailing, but what about my life made this happen. I've got a film I want to do about this. And I want to go out and sail some more."
     Jake Fisher, a Chicago entrepreneur, considers Pinkney one of his heroes, but says that Pinkney only considers himself heroic for one thing.
     "He said, `There was just one day in my life when I was hero. That was the day that the boat left Boston. It was a beautiful day, with people all over the place, wishing me well. When I reached over and took the anchor out of the water, that was the moment."
     Fisher asked him why that moment was heroic.
     "Because most people go through life with their boat tied up next to the pier," Pinkney told him. "What made me a hero was that I weighed anchor."

               —Originally published in the Sun-Times, October 30, 1994

     I caught up with Bill Pinkney by phone Sunday night at his home in Puerto Rico.
     "I feel great for a man of my age, great for a man of any age. We've been here, this is our 13th year," he said, referring to his wife of nearly 20 years, Migdalia.
     He first retired in 2003, then came back in 2007 and sailed the tour of the Amistad, a reproduction of the Spanish slave schooner whose 1839 uprising became an abolitionist cause and a widely-followed legal case (and, eventually, a Steven Spielberg movie). 

     "Nova Scotia, England, Portugal, Senegal, Sierra Leone, then I retired again, then I came back again, took the Amistad to Havana Cuba." Pinkney said. "Then I retired again for the last time and moved to Fajardo, on the east coast of Puerto Rico.
     Not everything has been gravy — his catamaran charter business, running passengers to the British Virgin Islands, was a victim of COVID, when American tourism to the island almost completely dried up.
    But generally life is good for Capt. Pinkney. He was presented with the Mystic Seaport Museum's "America and the Sea Award" in 2022. And he just released, "Sailing Commitment Around the World with Captain Bill Pinkney," illustrated by Pamela C. Rice, a very handsome children's book.   
    "I'm close to the ocean," said Pinkney, who doesn't own a boat but — even better — has a friend who owns a boat, and still gets out on the water from time to time.