By Ben Joravsky

In the last ten years, Bill Pinkney sailed around the globe and found himself back where he started. Specifically, he’s home in Chicago trying to raise money to erase the debts left over from his most recent transoceanic voyage, which he completed in June. “The hardest part of any voyage has always been raising money,” he says. “You know what they say–‘Everyone wants to go to heaven but no one wants to die.’ I learned that lesson years ago and I keep relearning it every day.”

It’s strange to imagine Pinkney scraping for cash, for his triumphs as a sailor have been widely celebrated. But he doesn’t come from privilege and he has no fortune to underwrite his adventures.

Raised on the south side by his mother, a domestic (his father was institutionalized when Pinkney was young), Pinkney graduated from Tilden Tech in 1954 and entered the navy. After leaving the service he lived in Puerto Rico, tending bar, dancing the limbo, and making just enough money to get by. “It was a great stretch of my life,” he says.

In 1961 he moved to New York City, where he worked his way up to a top marketing job at Revlon. He returned to Chicago in the 1970s and eventually found himself working under commissioner Leonora Cartwright in the city’s Department of Human Services. In the political reshuffling that followed Harold Washington’s 1983 election, Cartwright resigned and Pinkney was let go. He figured the time had come to stop the nine-to-five nonsense and go to sea.

“I started sailing in Puerto Rico and I loved it from the start,” he says. “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. You must be a quick study. You learn that if you put the sail up a certain way in a certain wind you’re going to get knocked down. So if you face that same wind, you have to do things differently unless you want to get knocked down again.”

After leaving City Hall, his goal was to circle the globe in a sailboat, rounding the southern tips of Africa, Tasmania, New Zealand, and South America. “To make it happen I needed several hundred thousand dollars,” he says.

He got a break when Bill Cosby, an old navy buddy, introduced him to Armand Hammer, the billionaire industrialist. Hammer donated $20,000 and hosted a fund-raiser that raised another $15,000. A small story in the New York Times caught the eye of Tom Eastman and Todd Johnson, pension fund investors in Boston. They wound up contributing about $240,000 to Pinkney’s cause. On August 5, 1990, he set sail from Charlestown Harbor in Boston aboard the Commitment, a 47-foot cutter.

He sailed south to Brazil then crossed the Atlantic, Indian, and Pacific oceans before returning to Boston. He was gone 22 months and at sea 259 days.

“People ask what I did during all that time alone. It’s simple. I talked to myself. I listened to music. I read 150 books, everything from Shakespeare to Clancy. My trip was being charted by dozens of schoolchildren and I found a big batch of letters waiting for me at every port I stopped at. There must have been several hundred letters. They’re very moving. The kids got captured by my journey and they poured out their hearts.”

He returned to a hero’s welcome, the subject of newspaper and magazine articles. He released a video of his trip that Cosby narrated, joined the New York Yacht Club, became a motivational speaker, and saw a stretch of East Monroe honorarily named for him.

But if he’d expected success to make it easier to raise money for his next venture–an Atlantic crossing that traced the Middle Passage route of the slave ships–he was wrong. He quickly learned that the rich don’t make their money by giving it away.

“Every corporate report you read has a picture of the guy in charge of looking out the window posing with some little kid who’s holding a giant unsigned check which is supposed to represent some generous contribution but is actually nothing more than peanuts–at least compared to the CEO’s bonus,” he says. “It’s difficult to get corporation support for a venture like mine. I don’t know why. If I knew I’d figure out a way to get the money. It’s a strange country. The things that should be important to all of us, the initiatives to give people a broader view of who we are and expose young people to things that don’t involve singing, dancing, or playing some kids’ sports for obscene amounts of money–they don’t get funded.

“I’m not belittling any of the honors I received. That street sign on Monroe between Columbus and Lake Shore Drive is in view of the building where my mother once worked as a domestic. At its dedication, my mother’s last living sister was there. It had tremendous meaning to me and my family. But that and a dollar-fifty will get me a ride on the CTA, and I’d better have a little extra change for a transfer.”

He’s most disappointed by the lack of support from wealthy black Chicagoans for his Middle Passage trip. “You would figure this voyage would be significant to them–an opportunity to symbolize the journey that brought us to this country, a way to honor our forefathers or to educate people about slavery. But there was no response. I don’t know why. Maybe it’s because the subject’s too painful. It’s certainly not because I didn’t try. I tried them all. I don’t mean to say that I get no black support. I get lots of support from working people. I’ll go on Cliff Kelley’s radio show and get people digging deep into their savings to give what they can. I’ve come to the conclusion that people who have less give a greater proportion of their money in donations than people who have more.”

Eventually he was able to pay some of his expenses by creating a curriculum around his voyage that he sold to dozens of schools across the country. A dozen teachers volunteered to sail with him for parts of his journey. Over 160 schools followed his trip, a process overseen by the Teachers Academy for Mathematics and Science, a local educational consulting group.

“We were Captain Pinkney’s liaison when he and his crew were at sea,” says Sherry Bushre, a professional developer with the academy. “Every day he checked in with us and gave us his longitude and latitude and meteorological observations. The classrooms could follow his progress by reading our reports on the Web.”

Pinkney, a tiny crew, and a rotating contingent of teachers made several stops along the African coast in the 78-foot yacht Sortilege, then were at sea more than six months before docking in Puerto Rico last June. He’s been in Chicago since July trying to find $200,000 to pay off the voyage.

Next spring he will captain a replica of the Amistad in a voyage partly financed by the state of Connecticut. He’ll sail the ship along the eastern seaboard, stopping at various points to pick up and drop off groups of schoolchildren.

He hopes to be out of debt by then. “I’ve never been deterred by a challenge–don’t tell me what you can’t do. People say ‘I can’t sail because I get seasick.’ But that’s no reason not to sail. Everyone gets seasick at times. I get seasick. But you don’t stay seasick forever. The temporary discomfort is outweighed by the long-term gain. I’ve learned that so much about success has to do with opportunity and attitudes. So many people have convinced themselves they can’t do something. It’s like dancing. Many people, particularly men, are taught to be ashamed of their bodies. They think they can’t do this or that with their hands because it would be effeminate. It’s very hard for them to get over that–they’re stiff, they’re afraid to move. Other people never get the opportunity, so they don’t realize what they’re missing. There’s no law that says black people can’t be great sailors. Why is Tiger Woods such a great golfer? Because his daddy took him to so many courses when he was a kid. Why are so many black kids good at basketball? Because there are basketball hoops in every city. In other words, the opportunity’s there, so people take it.

“I found my niche as a sailor. There should be nothing strange about that. It’s only strange if you assume that because I’m black I can’t be a sailor. We have so many assumptions that turn out to be false. Did you know that in Ghana most people like country music? It’s true. Go into almost any bar and you’ll see Africans playing country-western–and they played it well. There’s nothing written that says an African can’t play country-western. And there’s nothing written says a kid from the south side can’t sail. But they never have the opportunity even though the lake’s right there, so something great gets lost. Who knows how much talent is wasted this way?”

Art accompanying story in printed newspaper (not available in this archive): Robert Drea.