The purpose of this qualitative study was to explore the developing role of the Student Trustee. Utilizing a case study design and document analysis, this descriptive study examined the comments of 143 Student Trustees in Board meetings of the University of Massachusetts (UMass) System, the first in the nation to require Student Trustees, from 1970-–2015. The research questions sought to uncover the origins of the Student Trustee at the UMass System as well as how the role developed over time. The study concluded that Student Trustees provide a unique perspective that offers meaningful contributions to the discourse and decision-making processes of university Boards. The legislation that placed the first Student Trustee on the UMass Board was the result of contentious campus protests fueled by student dissatisfaction with higher education’s response to the Vietnam War, racism, and sexism, among other issues. Governor Francis Sargent proposed and signed that legislation in 1969 as a means to “move protest from confrontation to dialogue.” Student Trustees found success pushing the Board in a more progressive direction – adopting co-ed dormitories, providing greater due process in conduct matters, and asserting that students have primary responsibility over student policies and related matters. Student Trustees also pressed the Board to divest from companies operating in apartheid South Africa, and even to grant students an eight-day reprieve from papers and exams so they could campaign in the 1970 congressional elections. The role of the Student Trustee has expanded since Cynthia Olken took her place as the first Student Trustee in 1970. There are now five Student Trustees representing each of the five campuses in the UMass System. The two with voting power operate as regular board members and have the ability to serve on all committees, while the other three are ex officio non-voting members and can only attend open meetings of the full Board of Trustees. While more than half of the 143 Student Trustees made five or fewer remarks during their time on the board, there were many who spoke out frequently on issues related to finance, governance, and academics. Through their half-century of efforts, Student Trustees have earned a seat at the table and the praise of many university presidents, chancellors, and Board chairs that have used words like helpful, valuable, and significant to describe their contributions. As former UMass President Jack Wilson once exclaimed, “Having student representation on this Board is important.”