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Maynard, who arrived in the Seattle area separately from the Denny Party, was of a quite different demeanor than Arthur Denny's staunch Methodists. He lived with both his wife and his ex-wife, drank liquor (while the Denny Party were mostly teetotalers) and deliberately found someone to start a good brothel in Seattle, believing that prostitution was essential to the economic success of a frontier town of that time. Although he was originally one of the city's largest landholders and strongest boosters, he did not necessarily prosper with the city; among the reasons for this appear to have been that his friendly relations with Chief Seattle and other natives made him suspect to his fellow settlers, his Democratic politics were less than ideal for an increasingly Republican region]], his civic minded gestures helped others who did not always help him in return, and his drinking probably made him less effective toward the end of his life.
Seattle's Maynard Avenue South and Maynard Alley are named in his honor, as is a Pioneer Square bar.
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