John F. Kennedy was the 35th President of the United States, and the youngest man elected to the office. He was assassinated at the age of 46 in 1963. Arthur Ashe was an African American professional tennis player who won more than forty singles titles, including the Australian Open, the U.S. Open, and Wimbledon. He died in 1993 at the age of 49 of AIDS-related pneumonia contracted during heart bypass surgery years earlier. But imagine if the lives of JFK and Ashe had not been cut short? In this pair of speculative biographies, two writers suppose what might have been if JFK had lived long enough to serve out his presidency and what Arthur Ashe may have done to enhance his already notable legacy.