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Tayleure comments on Winter's sketches of England and indicates that he is an "intense admirer of the English people."
The letters mostly concern theatrical matters and travel plans. Addressed from Paris, London, New York, Washington, D.C., Cincinnati and Columbus, Ohio, and Boston.
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.
(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.
Concerning Mrs. Clifton Tayleure's health care. On letterhead of The Actors' Fund of America, New York. Addressed from 46 3d Avenue, New Brighton, Staten Island.
Smith would like to meet with Winter to discuss a matter of literary interest. Address on letter: 232 President Street, Borough of Brooklyn. Accompanied by envelope addressed to Winter.
Inquires about Winter's health following an injury in a railroad accident in California. On card stock with letterhead of Illuminated Lectures, W.F. Gilchrest, Litterateur, 217 Putnam Avenue, Brooklyn, N.Y.