Lendward “Lenny” Simpson, Jr., a Wilmington native, had the good fortune to be the next door neighbor to Nathaniel Jackson and to Dr. Hubert Eaton, who at the time was coaching Althea Gibson. With encouragement from all three, the 8 year old Lenny began to improve his tennis skills and he caught the eye of Dr. R. Walter Johnson, a legend who found the best African American athletes he could and introduced them to competitive tennis via his Junior Development Team. In 1964, Lenny defeated Dick Stockton to win the singles title at the US Lawn Tennis Association’s Eastern Boy’s 14s Championships in Forest Hills. Later that same year, he became the youngest male player, at that time, to ever play at the U. S. National Championships (now known as the US Open). He won his first round match but would lose to longtime mentor and friend Arthur Ashe in the second round.