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The Philleo-Norton papers contain the letters of Calvin W. Philleo, a a lawyer, author, and Free Soil Democrat; documents of pension claims for the widows and children of Revolutionary War veterans; legal documents entered in the suit of Sheldon et al. v. the Second School Society, Suffield; and the letters of Elizabeth Philleo as a young woman during the Civil War.

There are four main areas of interest in the Philleo-Norton papers. First are the letters of Calvin W. Philleo, written during the time that he was establishing his law practice in Suffield, launching into a successful literary career, and as he was involved with Free Soil state politics. Philleo's personal and political letters suggest that his interests ran well beyond the dull confines of his life as an attorney. His letters from 1848-1850 provide interesting commentary on Connecticut and national politics, and particularly on the Free Soil faction of the Democratic Party. The letters of C. F. Cleveland (who complains of the power of slave-interests in Connecticut), and congressmen Niles, Burnham, and Catlin provide insight into antebellum electoral politics in the state. Philleo's correspondence with editors at Graham's and Harper's reveals another side to his personality, the literary side, and provides a brief, curious look into the attitudes of an aspiring writer forced to deal with the realities of life as an attorney. Also of interest, Philleo wrote a curious, humorous letter to his brother-in-law, John, who had just gained employment on the railroad in Canada, comparing the "free" life of a railroad worker with the drudgery of law. Two letters from Calvin Philleo to his son Calvin W. Philleo, are dated March 2 and November 6, 1846, from Providence, Rhode Island. The earlier is an extensive discussion of the sale of a piece of city property valued at around $3,000 offered in exchange for the Canterbury farm, farm valuation and repairs, buildings and taxes, and Prudence's desire to travel west. The letter includes a note in Prudence Philleo's hand stating that she "never influenced your father to make but one trade in my life, and that was to buy the Cady place." The November 6, 1846, letter begins with Calvin addressing his son as his "only earthly friend" before explaining that the church has excluded him and that his mother (Prudence) intends never to live with him again except as separate boarders. She rejected his proposal to assist in building her a home with separate sleeping quarters, and now he needs a place to stay.

Secondly, Philleo's legal work preparing and representing pension claims for the widows and children of Revolutionary War veterans is well represented in the collection. The successful pension applications of the children of Nathaniel Pomroy and Jehiel Spencer are present and are apparently nearly complete (in copy). Further, there are printed items and miscellaneous correspondence, mostly with Commissioner of Pensions, L. P. Waldo, relating to pension applications, and including instruction sheets for completing applications, a pamphlet containing rules for applying for bounty land, and a sheet indicating materials required for submission to limit fraudulent applications. Photocopies of the Pomroy and Spencer applications as submitted to the Pension Office are included.

Thirdly, the legal documents entered in the suit of Sheldon et al. v. the Second School Society, Suffield, are an intriguing record of a local tax revolt in 1852. Hezekiah Sheldon and his co-petitioners to the court objected strenuously to the School Society's plans to build a new school building using tax money collected locally.

Finally, the letters of Elizabeth Philleo and her sisters contain occasional comments of general interest regarding the lives of young women during the Civil War. Lucy Norton's reactions to the defeat at Bull Run in 1861, and the news that Elizabeth relays of a family friend serving as an officer in the 55th Massachusetts (Colored) Regiment are particularly noteworthy, but it is also interesting to reconstruct the series of lectures, panoramas, and social gatherings Elizabeth attended in Connecticut and Boston during the war. There are two letters of Calvin Philleo, Sr., and Prudence Crandall Philleo, one of which, written in 1870, contains some brief reflections on the power of religious conviction in Calvin's life, from the time he was involved in revivals in New York State through his move to Illinois.