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The letters mostly concern theatrical matters and travel plans. Addressed from Paris, London, New York, Washington, D.C., Cincinnati and Columbus, Ohio, and Boston.
Tayleure comments on Winter's sketches of England and indicates that he is an "intense admirer of the English people."
Letter about first American production of Sardou's Patrie.
Tayleure compliments Winter on his memoir The press and the stage. Tayleure further indicates that, despite his feeling that he took the "wrong pathway," it is too late for him to retrace his steps, so he moves forward "with more peace of soul however than Macbeth." Also discusses a quotation from Samuel Butler's Hudibras, which Tayleure believes Winter misquoted.
(1) A letter of sympathy, likely on the death of Winter's son, Arthur; (2) On her husband Clifton's illness and business troubles; with accompanying envelope addressed to Winter at #17 3rd Avenue, Fort Hill, New Brighton, Staten Island. Winter's annotation on envelope: "Mrs. Mary A. Tayleure. Rec'd April 11, 1891. - News of the death of Clifton W. Tayleure came on April 13." (3) Thanks Winter for his card of remembrance and discusses difficulties her family is experiencing. Addressed from various locations in New York.
(1) asks for a letter of introduction to give to Mr. Toole; several other letters mention plans to meet various acquaintances. (1) on letterhead of E.W. Vanderhoof, 72 Broadway, New York; (2-6) on letterhead of Union Club, Fifth Avenue & 21st Street; (7-8) addressed from Clifton Springs.
Concerning his father's upcoming funeral and his wishes for Winter to recite or read "Just as I am." Addressed from No. 1 Warren Place, Brooklyn.