For the students in Dhamana Shauri's fifth grade class at the Nathan R. Goldblatt Elementary School on Chicago's West Side, learning has never seemed so personal. Their classroom computer shows a world map tracing Captain Bill's sailing journey. A red line crawls down the screen from New York City until it stops and blinks at a point marking the Brazilian port of Salvador, Bahia. Click to the next screen and there are questions from Captain Bill himself. "How many miles have I traveled?" he asks. "In what direction was I traveling? Until next time, this is Captain Bill aboard the yacht Commitment signing off—and remember to keep dreaming 'cause dreams do come true."

No, Captain Bill is not a character from Saturday morning TV; he is William Pinkney, 54, and he is circumnavigating the globe alone aboard a 47-foot yacht. Departing last July from New York City, Pinkney set a 27,000-mile course that will take him around the five southernmost capes—South Africa's Cape of Good Hope, Cape Leeuwin in Australia, South-west Cape in Tasmania, Stewart Island Cape in New Zealand and Cape Horn at the tip of South America. On returning to his starting point, which he hopes to do next June, Pinkney will become one of a handful of Americans and the first black skipper ever to achieve the feat.

Paradoxically, while Pinkney sails the world alone, he is enjoying the company of thousands of school kids like those in Dhamana Shauri's class in Chicago, Pinkney's own home port. From the start, this trip was meant to be educational; Pinkney wanted above all to send a message to the kids about meeting challenges and persevering toward a goal. Thanks to a satellite hookup and a monthly classroom newspaper, 75,000 pupils throughout the Chicago system (and some 21,000 in Indiana plus an even larger audience in other school systems around the country that may join the program) are traveling vicariously with Pinkney, following his day-to-day progress and even communicating directly with him via his on-board computer. They will hear about the people, languages and customs that he will encounter at his stopovers, work on the math required in navigation and delve into the music and literature of the sea.

Pinkney has personal reasons for embarking on the trip as well. "When you get to a certain point in life," he says, "you think, 'What have I done?' And so very few people do a damn thing about it." So Captain Bill is doing something about it, and he's doing it the hard way—no shortcuts through the Panama or Suez canals. "It sounds like I'm a purist," Pinkney says, "but the Lord didn't intend us to go around the world through canals, because He didn't put them there."

Although he holds no college degree, Bill Pinkney is a gifted teacher. He got that way by being "an addicted reader of anything with print on it," he says, and from the experiences of his extraordinarily varied life. Among other jobs, he has worked as an X-ray technician, a bongo-drum player, a bartender, a limbo dancer, a deckhand on a Caribbean freight-carrying sloop, a marketing executive and a Chicago city official.

Growing up in a single-parent family on Chicago's South Side, Pinkney once aspired to a career in architecture and attended Saturday art classes in pursuit of his goal. But necessity forced him to get a paying job right after finishing high school, first at a local hospital and then through a Navy enlistment that lasted eight years. While training as a hospital corpsman at Bainbridge, Md., his buddy was another Bill—Cosby. Their friendship was reinforced when both moved to New York City in the mid-'60s after leaving the service. "I used to moonlight in an Afro-Cuban band in Greenwich Village, and Bill was doing stand-up comedy in nightclubs," Pinkney recalls. "Over the years we didn't see a lot of each other, but whenever we did meet, there was always a strong camaraderie."

Married briefly during his Navy years (he has a grown daughter and two grandchildren), Pinkney remarried in 1965, this time to a Brooklyn, N.Y., schoolteacher named Ina Brody. A rabbi presided at the ceremony, since Ina is Jewish and Bill had embraced Judaism at the age of 12 after concluding, Ina says, that Christian America had failed its black citizens. "We've never tried to make any statement about our [racial] situation; it just was what it was," says Ina, who now runs her own special-order dessert bakery.

There were two other turning points to Pinkney's life during his years in New York. To find an outlet for his artistic talents, he went to beauty school to study with noted film-makeup artist Dick Smith. Pinkney proved such an apt pupil that he was soon a successful free-lancer working with stars such as Red Buttons, Jaclyn Smith and Roberta Flack. In time he also became, as the Wall Street Journal reported, the acknowledged expert in the field of cosmetics for black women. On the basis of his growing reputation, Revlon recruited him in 1973 to be one of their marketing directors.

At about the same time, Pinkney also discovered that he liked sailboats, starting with radio-controlled miniatures bobbing in the Central Park model yacht basin. By 1965 he was haunting the waterfront in his spare time, begging for berths on yacht deliveries to Florida and the Caribbean. Even when he moved back to Chicago to take a cosmetic marketing job with Johnson Products in 1977, he kept up his sailing on the Great Lakes, notably in seven rigorous (333-mile) Chicago-to-Mackinac Island races. Last year Pinkney was elected the first black commodore of Chicago's Belmont Yacht Club. As for his interest in solo sailing, that came about accidentally, reports Ina, "when his crew forgot to show up for a race on one occasion."

Pinkney's business career ended when the bottom fell out of the market for specialized cosmetics for blacks in the late '70s. In 1983 he became the director of public information for Chicago's Department of Human Resources but was swept out after four years in a change of city administrations. By then he was tired of the office routine anyway. "I wanted to do something significant," he says. "It had to be in the realm of sailing because that's what I know best."

Thus was born his World Challenge Fund, headquartered in a cubbyhole at the rear of Ina's catering kitchen. For five years he sought sponsors to cover the expected $350,000 cost of Project Commitment. Poet Maya Angelou sent a donation and a personal note, and industrialist Armand Hammer, steered to Pinkney by their mutual friend Bill Cosby, sent $25,000 as a way of being "part of your journey." A complex deal secured use of the yacht Commitment from a group of Boston investors. The John D. and Catherine T. MacArthur Foundation agreed to fund the school programs, while Motorola and IBM contributed computer and telecommunications gear. Hormel sent canned foods, and Ciba-Geigy provided medicine that Pinkney has depended on since a 1981 middle-ear infection left him partially deaf and prone to seasickness.

Captain Bill, of course, knows the risks of ocean sailing, from physical and psychological stress to the possibilities of illness, equipment failure, collision at sea or even sinking. But prior to his departure, he exuded confidence. Pointing to the satellite navigation system that will track him every mile along his route, he proclaimed, "I couldn't get lost if I wanted to," to which Ina added, "I'm the luckiest woman alive since I'll know where my husband will be 100 percent of the time."

So will a lot of Chicago school kids. In the months ahead, they will plot and chart his positions, read a monthly column by him in the classroom newsletter, try math games, work crossword puzzles and, if they wish, ask Captain Bill how he's feeling. "Here's a Chicagoan who went to city schools whom the children can relate to," says Chicago Superintendent of Schools Ted Kimbrough. "When it's all over, he'll be a legend for the kids."

—Dan Chu, Bonnie Bell in Chicago

  • Contributors:
  • Bonnie Bell.