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In 1866, the year after the end of the Civil War, Henry Shaw, a retired St. Louis merchant, approached St. Louis mayor James S. Thomas with a proposition. Shaw, who had already established the "Missouri Botanical Garden" on part of the estate surrounding his country villa, wanted to donate a still larger tract to the city of St. Louis as a pleasure ground for the citizenry. According to a contemporary, Shaw believed that parks were important "not only as ornaments to a great city, but as conducive to the health and happiness of its inhabitants and to the advancement of refinement and culture."

At the time Shaw made his proposal, there were only eleven parks in the city -- Benton Park (created from city common land in 1866), Exchange Square (donated 1816); Carr Square (donated 1842), Gravois Park (created from city common land in 1812), Hyde Park (purchased in 1854), Jackson Place (donated 1829), Laclede Park (from city common land 1812), Missouri Park (purchased / donated 1854), St. Louis Place (donated 1850), Washington Square (purchased 1850), and Lafayette Park (from city commons 1844). At almost thirty acres, Lafayette Park was by far the largest of the pre-existing parks, more than twice as large as any other. It was also the only existing park to be governed by a board of commissioners rather than by the municipal park commissioner.

Shaw's plan called for a park of two hundred and sixty-seven acres, governed - as was Lafayette Park - by an appointed board. His donation was complicated by the fact that the land he sought to donate stood outside the city's boundaries -- it required an act of the state legislature "to create, establish and provide for the government of Tower Grove Park, of the City of St. Louis" (1867). The governance of the parcel bounded by Grand Avenue on the east, Kingshighway on the west, Magnolia Street on the north, and Arsenal Street on the south was to lie in the hands of a board of commissioners of not more than seven persons, selected by and including Mr. Shaw during his lifetime, and selected thereafter by the Missouri State Supreme Court. Improvements to the park were to be funded by the city itself through the issuance of bonds; its maintenance was to be provided by additional property taxes collected within the city and county of St. Louis." The only conditions Shaw imposed on his gift were 1) that it "shall be used as a park forever," and 2) that an "annual appropriation" be made by the city "for its maintenance."

In all of these negotiations, Henry Shaw showed himself to be not only a generous philanthropist; he was also revealed to have lost nothing of the dedication and good business sense that had made him successful enough to retire from active commerce at age 39. If it was Shaw's mercantile skill that had made it possible for him to establish the park, it was Shaw's pursuits after his retirement -- his fascination with plants, particularly trees and shrubs, his enjoyment of the classics to which he had been introduced as a schoolboy in Sheffield and at Mill Hill School, and his love of European travel -- that make Shaw's Tower Grove Park a particularly striking example of the Victorian pleasure ground.

According to a contemporary:
The Board of Commissioners, of course, consulted together respecting the inception and progress of the work but the experience acquired by Mr. Henry Shaw in the creation of the Missouri Botanical Gardens, in many years devoted to the study of botany and arboriculture, and to the best methods and designs for landscape gardening, as suggested in the works of such eminent authors as Sir Uvedale Price , Repton , Gilpin , Loudon , Downing , and Alphand's "Parks and promenades of Paris ," etc., naturally place him in a position to decide the plan to be adopted. In addition to his opportunities for study and experiment Mr. Shaw, after his retirement from active business, had spent eight years in Europe where he observed closely the various features and systems of public pleasure grounds in England, France, Germany and other countries; and subsequent to his return to St. Louis he also derived much information from examining the records of the park authorities in the cities of the United States.