Little is known of the painter William Clarke, but certainly Levin Winder (1757 – 1819) numbers among his most prominent sitters. A Marylander, Winder served in various Maryland regiments during the American Revolution. He then entered the political arena, rising through the ranks to become governor of Maryland from 1812 to 1816. At the time of this painting, Levin was just completing a term as speaker of the Maryland House of Representatives. Levin’s lawn, seen in the background, would have been perceived as an improved or “cultivated” space, a mark of his status and wealth.