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T. J. McIlwaine served as superintendent of Prince Edward County Public Schools from 1918 to 1965, a tenure that spanned nearly five decades of dramatic change in American public education. A dedicated advocate for expanding educational infrastructure, McIlwaine played a central role in modernizing both rural and urban schools throughout the county. At the outset of his career, he noted that “two-thirds of the Negro school buildings were one-room schools,” and over the years, he worked to improve facilities for both Black and white students. However, these improvements were constrained by limited funding and entrenched racial inequities. In the case of the R.R. Moton High School, he later expressed disappointment at its inadequate condition but claimed he had been unable to secure more than the $40,000 allotted by the county Board of Supervisors for its construction.

Despite his administrative accomplishments, McIlwaine became a controversial figure during the 1951 student strike led by 16-year-old Barbara Johns at Moton High School. When the students walked out to protest overcrowded and substandard conditions, McIlwaine refused to visit the school or engage with the striking students unless they returned to class. When student leaders later presented their grievances, he downplayed their concerns, pointing to legal constraints and offering vague promises of eventual improvement while rejecting any move toward integration.