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Capt. William “Bill” Pinkney’s journey into becoming the first Black person to sail around the globe took some unlikely turns. The Chicago native was born September 15, 1935.

Pinkney was trained as an x-ray technician before joining the U.S. Navy. After the military, Pinkney worked a variety of jobs, including becoming a professional limbo dancer in Puerto Rico. He also worked in cosmetics as a make-up artist before taking a marketing manager position with the Revlon company in New York.

Returning to Chicago, Pinkney took a city government job in the early ‘80s, but his passion for the seas, which he picked up in Puerto Rico as a part-time crewman, never waned. With the help of investors like businessman Armand Hammer, who Bill Cosby put in contact with Pinkney, the construction of a one-man sailboat to take on the grueling journey was in motion.

Part of Pinkney’s desire to take on the journey was to leave a legacy behind for his grandchildren and to inspire others to dream big. So at age 55, he set out on the dangerous and lonely journey on August 5, 1990 from Boston Harbor. The trip took 22 months, longer than expected due to several instances of weather and other factors. He returned to Boston on June 9, 1992, penning a children’s book about his experiences.

In 2000, Pinkney took on another journey, this time alongside schoolteachers. Along with the teachers and a crew, Pinkney recreated the sailing of the Amistad, the slave ship taken over by slaves in 1839, when it was seized off the coast of Long Island, New York. In 2003, Pinkney married his third wife and announced his retirement from sailing for anything else but pleasure.