Winter entered politics in 1947. While in law school, Winter was elected to the Mississippi House of Representatives. He was subsequently re-elected in 1951 and 1955. In his early days as a representative, he was appointed as a Trustee of the Mississippi Department of Archives and History; Winter continued to serve on this agency board throughout his public and private life. In 1955 Winter, encouraged by his friend, Governor James P. Coleman, launched a bid to unseat Speaker of the House Walter Sillers Jr. and replace him, the first attempt to unseat an incumbent speaker since 1928. After Sillers offered to guide Coleman's legislative program through the House, Coleman advised Winter that he could not publicly support him and urged him to concede. Winter and his supporters decided to press on with their campaign, and in the vote for the speakership he lost, earning 40 votes in comparison to 94 votes for Sillers. Three months later Tax Collector of the State of Mississippi Nellah Massey Bailey unexpectedly died. Coleman summoned Winter from his desk on the House floor to his office and offered him the job, knowing that it would provide him with a high-paying salary and give him a platform from which he could make future bids for statewide office. Winter accepted, and the appointment was announced two days later.