Nellah Massey Bailey

In March 1944, during World War II, Bailey became the state chair of the newly established Mississippi Joint Recruitment Campaign.[14] Sponsored by the Mississippi Office of Civilian Defense, the campaign sought to conduct a statewide house-to-house survey of women who were eligible to serve in the four women's branches of the United States Armed Forces: the Women's Army Corps, the Navy Women's Reserve, the Coast Guard Women's Reserve, and the Marine Corps Women's Reserve.[15] 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.[16]

Bailey believed that women had a duty to fight in the war, saying: "We leaders of our state must break down the prejudice which exists in Mississippi against women in the service. It is an honor for a young woman to serve her nation in this day of strife." 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.[17]

As state chair, Bailey appointed an executive committee, consisting of statewide leaders of civic, fraternal, and service organizations as well as representatives of the women's branches of the Armed Forces, and mayors across the state were directed to form local committees to conduct the canvasses in each community.[18] 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.[19] 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."[20] The campaign was the first of its kind to be established in any state;[21] Georgia later developed a similar program based on Mississippi's example.[22]

According to the Clarion-Ledger, many people had expected Bailey to run for statewide office.[23] 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.[24] No appointment was ultimately made when senators reached an agreement that Bilbo would remain under consideration while he underwent treatment for oral cancer.[25]

Incumbent Mississippi state tax collector Carl N. Craig announced his intention to run for state auditor on February 15, 1947.[26] 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.[23] She used her late husband's name in her political activities, campaigning as "Mrs. Thomas L. Bailey".[27] At her candidate qualification, Bailey said: "The next four years will see the accomplishment of many of the dreams and programs of Governor Bailey, and it is but natural that I want to be a part of that administration. Tom Bailey worked hard for Mississippi, and I shall endeavor to give my best to the state he loved so well."[23]

Two other candidates had announced their intention to run for state tax collector: O. D. Loper, who worked in the state auditor's office, and Potts Johnson, a farmer from Jackson.[28][29] 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. Any man who would claim that a woman should not hold at least one out of the ten elective state offices is insulting the intelligence of every woman voter in Mississippi. A woman can supervise this tax collecting work as good as a man, and Mrs. Bailey's capacity as an executive is well known in Mississippi.[30]

Bailey defeated Loper in the Democratic primary with 60.5 percent of the vote,[31] and was unopposed in the general election.[32] She was sworn in as state tax collector on January 19, 1948, becoming the first woman to hold statewide elected office in Mississippi.[33]

Mississippi's tax on liquor figured prominently during Bailey's tenure as state tax collector. At the time, Mississippi and Oklahoma were the only two remaining dry states that had not repealed prohibition legislation.[34] 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.[35] During Bailey's term, black market tax revenues reached record highs.[34] The state tax collector's office took a ten percent commission of all taxes, making the position the most lucrative elected office in the state (by comparison, the governor's annual salary was $15,000).[36]

C. W. Pitts, a former state highway patrolman, announced his candidacy for state tax collector in April 1951, challenging Bailey in the Democratic primary. He ran on a platform that advocated for the repeal of the black market tax.[37][38] Robert W. May, the incumbent term-limited Mississippi state treasurer, also entered the race that month. 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". Bailey responded by arguing that the profits were divided among the 17 office employees.[39]

Bailey defeated Pitts and May in the Democratic primary election, garnering 54.4 percent of the vote and avoiding a runoff election.[40] She was unopposed in the general election and was sworn into her second term on January 21, 1952.[41][42]

The 1955 Democratic primary for state tax collector had four candidates, including Howard H. Little, a member of the Mississippi Public Service Commission.[43] Bailey received 44.8 percent of the vote in the election; because no candidate received a majority of the vote, the primary went to a runoff between Bailey and Little, who received 30.0 percent of the vote.[44] Despite the other two eliminated candidates endorsing Little,[45] Bailey defeated Little in the runoff election by a five-point margin.[46]