By 1956 there had been few real social advances for women in golf. The creation of the LPGA in 1950, spearheaded by Babe Zaharias and Patty Berg, opened the door for women professionals. But when Gregory stepped onto the 1st tee at Meridian Hills six years later, the burning issue in the women's game was dress codes rather than integration. In 1954 the U.S. Supreme Court had ruled on the landmark case of Brown v. Board of Education, banning racial segregation in public schools. In December 1955 the Reverend Martin Luther King Jr. had led the bus boycotts in Montgomery, Ala.
In contrast, the women's amateur circuit of the 1950s was a sort of enclave of golf debutantes. The players were fresh-faced, young white women who vied for silver cups on a tour of private clubs and exclusive resorts. The era produced great players, among them Mickey Wright, JoAnne Carner, Marlene Streit, Barbara McIntire and Anne Sander. But following the circuit was expensive, and while a few had jobs, many players were well-to-do.
The opposite was true of Gregory, who was born in Aberdeen, Miss., on July 25, 1912, the daughter of Henry and Myra Moore. Her parents died when she was a child, and she went to live with a white family, the Sanderses, for whom she served as the maid. In '38 she married Percy Gregory, and they moved to Gary, Ind.
"That family cried like babies," Gregory said of her leaving. "They said people in the North were so cold and that I didn't deserve being treated like that. I said, 'Mrs. Sanders, you've prepared me very well for mistreatment.' "
The new Mrs. Gregory was a good athlete. She took up tennis and soon won the Gary city tennis championship. In 1943 she joined the Chicago Women's Golf Association (CWGA), a black organization, and took golf lessons from Calvin Ingram, a good black player who worked at a Chicago club.
It wasn't long before she was winning amateur tournaments, including the CWGA championship, the Joe Louis Invitational in Detroit and the championship of the United Golf Association (UGA), a national organization for black players. Those events drew little or no notice in most major newspapers, but black papers hailed her as "The Queen of Negro Women's Golf," and in 1947 George S. May, a golf promoter in Chicago, invited her to play in his open invitational tournament, the Tam O'Shanter. She was the only black woman in the field.
"Mr. May told me if anyone said anything to me, to let him know," Gregory said. "No one did. The galleries were just beautiful to me. But I was lonely. For a whole week I didn't see any black people.
"My neighbors drove up from Gary to see me play the final round and, when I saw them, that's the only time I felt funny. It just did something to me to see my black friends among all those white people, and I cried."
The Gregorys lived in a comfortable house in Gary, where Percy worked for U.S. Steel. Ann was a caterer for the University Club, served on the Community Chest and United Fund committees, and in 1954 became the first black appointed to the Gary Public Library Board.
In 1956 the Chicago group became the first black organization to join the USGA, thereby making Gregory eligible for its championships. She immediately entered the 1956 Women's Amateur and drove to Indianapolis with Jolyn Robichaux, a friend from the CWGA.