James Winne was graduated at Hamilton College in 1877, having spent one year also at Cornell University. Before his graduation, he taught Latin and Greek one year in Troy Academy. In the fall of 1877, he became principal of the union school at Holland Patent. Two years later, he was chosen principal of the Canastota union school, where he taught for six years. In 1885, he came to Ilion as principal, and the following year was made principal of the High school at Poughkeepsie, where he conducted the school successfully for fifteen years. He was elected president of the New York state Academic Principals' Conference in 1891. He resigned the office on leaving the State to become superintendent of schools in Greenwich, Connecticut. The year 1901-2, he devoted to study and travel in Europe. In 1893, he was appointed principal of the Allegheny Preparatory school at Allegheny, Pennsylvania. [This was the position he occupied in 1904.]