Andrew Jackson was one of the trusted stable workers at Belair, and William Woodward regarded him as a consummate horseman. Born in Kentucky in the 1850s, the son of slaves, he did not know his exact birth date. He showed early talent with horses and at some point was leased by his family to a horse trainer in New York. His riding skill led him to become a jockey, and he rode his first winner at Saratoga in 1872 while riding for the stable of Maryland Governor Oden Bowie. After coming to Maryland, he worked at Fairview, the Bowie family plantation near Belair. In 1900, James T. Woodward hired him to work at Belair, where William Woodward credited him with spotting Capt. Hancock, a $60 stud horse bought from a barn in Collington. That stallion, together with three $100 mares purchased by Woodward, formed the beginning of the twentieth-century Belair Stud. Handling all things equine, Jackson was the trainer of record for Belair's first race winner at Marlboro Race Course in 1909, when the colt Aile d'Or, by Capt. Hancock out of Charemma, won. He remained at Belair until his death in 1932, was buried at Whitemarsh Cemetery at Sacred Heart Church, and received a tombstone donated by William Woodward, who later privately published A Memoir of Andrew Jackson, Africanus in 1938 as a further sign of his respect and admiration.