[16] It was during her time as assistant librarian at the Meridian public library that Massey met Thomas Lowry Bailey, an attorney who was on the judging committee for a local word contest.

Thomas Bailey began staying later each evening, after the other committee members had left, to help Massey with the building closing procedures; they eventually started dating, and were married on August 22, 1917.

[19] She remained in the role until Governor Bailey died on November 2, 1946, from surgical complications during a procedure to remove a spinal tumor.

[20] In March 1944, during World War II, Bailey became the state chair of the newly established Mississippi Joint Recruitment Campaign.

[22] The program's mission was not to conscript eligible women, but rather to provide enlistment information to those interested in joining a branch of service.

She pushed back against claims that women would become "less feminine" after serving in the Armed Forces, and said that they would gain "poise and character" through their service.

[25] Initially planned to be a three-week campaign, it received enthusiastic support across the state, and the national women's branches of the Armed Forces extended the time that their representatives would visit communities for further recruitment.

[26] Althea O'Hanlon, a field liaison representative for the national Office of Civilian Defense, remarked that "Mississippi has blazed the trail for a new era in the recruitment of women for the various services.

[30] In January 1947, when the U.S. Senate initially refused to re-seat Mississippi senator Theodore G. Bilbo due to admissions of racist voter suppression and bribery, the Jackson Business and Professional Women's club endorsed Bailey for the potential senatorial interim seat, though Bailey declined to comment on a potential appointment.

[31] No appointment was ultimately made when senators reached an agreement that Bilbo would remain under consideration while he underwent treatment for oral cancer.

[33] Bailey qualified for the open race for state tax collector on May 17, 1947; she was the first woman to run for statewide office in Mississippi.

[35][36] Upon learning that Bailey entered the race, Johnson withdrew his candidacy and endorsed her, saying: We men in Mississippi have been asking women to vote for us for state offices ever since woman suffrage was adopted.

[42] However, difficulty in enforcing the law, particularly in "wet areas" of the state, resulted in a ten percent "black market" tax on all sales of liquor, despite its illegal status.

During a candidate forum, May criticized Bailey and accused her of overreliance on unelected deputies, while Pitts pledged to give half of his collection profits to charity and said that the position of state tax collector should be "a man's job".

[49][50] The 1955 Democratic primary for state tax collector had four candidates, including Howard H. Little, a member of the Mississippi Public Service Commission.