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This collection is made up of letters that Phil Clifford, a student at the Phillips Exeter Academy, wrote to his parents, Mr. and Mrs. Arthur Clifford of West Medford and Boston, Massachusetts, and to his sister, Lizze. The letters detail Clifford's academic and monetary struggles.

This collection contains 62 letters and 2 postcards that Phil Clifford, a student at the Phillips Exeter Academy, wrote to his parents, Mr. and Mrs. Arthur Clifford of West Medford and Boston, Massachusetts, and to his sister, Lizze, from October 16, 1914-May 13, 1917. During his time at the school, he assured his parents of his efforts to raise his grades, seldom higher than Cs, and discussed leisure activities such as attending football games and visiting the area around Exeter, New Hampshire. In his second year, he joined the school's Kappa Delta Pi fraternity. Along with academic troubles, Clifford faced persistent financial difficulties and frequently asked his parents to send him money and postage stamps. On several occasions, he provided itemized lists of recent expenses. In his final letter (May 13, 1917), he mentioned his fraternity's financial shortfall, caused by the loss of several members to the United States Army after the country's formal entrance into World War I. Two postcards have images of the academy's chapel and library, respectively, and two advertising cards promote Arthur Clifford's produce company, A. Clifford & Co.