Arthur Ashe was born at St. Philip Hospital for Negroes in Richmond on March 10, 1943. The hospital existed because Black patients were not admitted to white hospitals in Jim Crow Virginia. As a child, Ashe was denied entry to tennis tournaments held on the city's best courts, simply because he was Black. He was not allowed to practice on those courts either. He learned to play tennis on segregated public courts in Brookfield Park, taught by Ron Charity and later by Dr. Robert Walter Johnson, the Lynchburg physician who also coached Althea Gibson. In 1960, at seventeen, Ashe moved to St. Louis to attend Sumner High School, the first public high school for African Americans west of the Mississippi. He left Richmond because Richmond would not give him the courts. He won the U.S. Open in 1968, Wimbledon in 1975, the Australian Open in 1970. He became the first Black man ever to win any of those tournaments. He died of complications from AIDS in 1993, having contracted HIV through a blood transfusion during heart surgery. He had spent his final years working publicly on AIDS awareness and on civil rights causes.

Paul DiPasquale, a Richmond sculptor, met Ashe in 1992 when a mutual friend, Wyatt Kingston, made the introduction. DiPasquale asked permission to design a statue of him. Ashe agreed. DiPasquale created nine crayon and pencil studies before Ashe's death in 1993. After Ashe died, his widow Jeanne Moutoussamy-Ashe approved the studies and recommended Virginia Heroes Incorporated to handle the funding. In December 1994, the design was first unveiled in plaster form at the Arthur Ashe Center. With the urging of Richmond City Manager Robert Bobb, the Richmond City Council approved placement of the statue on Monument Avenue in June 1995. Mayor Leonidas B. Young II supported an alternative location: Byrd Park, which had been whites-only until 1956. The Council chose Monument Avenue.

On January 1, 1996, the Richmond Times-Dispatch published a letter by Jeanne Moutoussamy-Ashe arguing that the monument as planned "honors Richmond, Virginia, more than it does its son, his legacy, and his life's work." Her husband, she wrote, had expected the monument to stand in front of an envisioned African-American sports hall of fame, not among the Confederate generals he had grown up unable to look at without complicated feeling. A few days later she reached an agreement with Citizens for Excellence in Public Art, a group led by gallery owner Beverly Reynolds: together they would raise $20 million for the sports hall of fame, the DiPasquale statue would eventually move there, and meanwhile a million-dollar international competition would be held to find a better design for Monument Avenue. The group had raised $200,000 toward that goal when the Richmond City Council shut their plan down. The statue went up where the Council had decided it would. Unveiling was July 10, 1996.

The statue has never quite landed as its sculptor intended. In 2017, Mental Floss placed it third on a listicle titled "10 Unintentionally Horrifying Statues of Famous People," describing Ashe as "frozen forever in a state of seemingly mocking [the children] for their lack of height." DiPasquale defended his work when Salon reached out to him: "If you always see what you always saw, you will always get what you always got. Judging art, like life, depends on what you bring to it, I'm sure." The placement of the statue itself has done more for its meaning than the bronze ever could. The contested integration of Monument Avenue - on land originally laid out to memorialize a war fought to keep Ashe's grandparents in bondage - made the Ashe Monument into a kind of public argument about who Richmond claimed. The Confederate monuments on the avenue had been put up between 1890 and 1929, during the height of the Lost Cause movement, when white Southerners worked to remake the meaning of the Civil War in their favor. Ashe's statue, almost a century later, was the first crack in that program.

On July 1, 2020, amid the protests that followed the murder of George Floyd in Minneapolis, Mayor Levar Stoney ordered every statue of Confederate generals on city property taken down. By the end of that summer, Lee, Jackson, Stuart, Davis, and Maury were gone. The only statue still standing on Monument Avenue was Arthur Ashe. Two weeks after Stoney's order, on July 16, 2020, someone vandalized the Ashe pedestal with spray paint reading "White Lives Matter" and "WLM." A man who claimed to be the vandal told passersby, "You put it on our statues, I'll put it on yours." The Ashe family told the city of Richmond they could remove the statue if doing so was necessary to protect it. The city kept it where it was. Today, on a wide boulevard once meant to honor the men who had fought to keep Black Americans enslaved, the figure of Arthur Ashe stands surrounded by children - reading, learning, holding the future. Richmond made the statue a kind of accident of history. History decided he was the one the city kept.