He graduated from a technical high school, having pivoted his ambitions to architecture, but ended up joining the Naval Reserve hoping to travel and see the world. He encountered racism from the get-go: He wanted to specialize as a hospital corpsman, but was encouraged to be a “steward’s mate,” essentially a valet to the officers, where he “could be with his own kind,” he recalled one personnel officer telling him. Mr. Pinkney prevailed, went on to train as an X-ray technician and served on various ships.
After he left the service, Mr. Pinkney, a gregarious, curious and restless man, worked as an elevator mechanic, a limbo dancer (at which he excelled), a conga player, a makeup artist on soft-porn films and then on more conventional fare, a cosmetics executive at Revlon and other companies, and a public information officer for the city of Chicago. He had fallen in love with sailing while living in Puerto Rico after his Navy service, a bittersweet period, he wrote in his book, because he had moved there after fleeing an early marriage, leaving his young daughter behind.
“I became what too many Black men became,” he wrote in his book, “‘a deserter.’ I ran then and in some ways am still running.”
He lived for a time in New York City and crewed on friends’ boats in the Northeast; he was always the only Black man on board. (He also sailed model yachts in a Central Park pond.) And while in New York he converted to Judaism, the culmination of a spiritual quest that he had embarked on after his divorce and that sustained him on his journey years later.
Mr. Pinkney began sailing in earnest on Lake Michigan when a job took him back to Chicago. His first sailboat was a 28-foot Pearson Triton he named Assagai, for an African spear. When he turned 50, having climbed the corporate ladder, he asked Ina Pinkney, whom he had married in 1965, if she would be unhappy if he went to sea. “I’d be unhappy if you didn’t go,” she told him.
