The patriotic figure of Uncle Sam is based on an actual man, Samuel Wilson, of Troy, New York, who won a government contract to supply meat to troops during the War of 1812. His characterization as a country fellow wearing a top hat and striped pants has its roots in the Revolutionary War figure of Yankee Doodle, also known as Brother Jonathan, and was standardized by the late nineteenth century in the political cartoons of Thomas Nast. In this whirligig, Uncle Sam pedals a modified high-wheeler when the wind turns the front propeller.
The whirligig was found in upstate New York, in an area near the Canadian border. This may explain the appearance of the American flag on one side and the Union Jack on the other. Although the Union Jack never functioned as a national flag, it symbolized Canada’s status as a British sovereign state, and its use became more prominent during pivotal historical moments. In 1897, when Queen Victoria’s Diamond Jubilee was celebrated, the Union Jack emphasized Canada’s participation as a British subject. And in 1900, about two thousand students from McGill University demonstrated throughout Montreal, attempting to force newspapers, shops, and even the city hall to fly the Union Jack, a sign of growing imperialism that reached its height during the South African War (1899–1902) with Britain’s pleas for imperial solidarity within her empire.
Stacy C. Hollander, "Uncle Sam Riding a Bicycle Whirligig," in American Anthem: Masterworks from the American Folk Art Museum (New York: Harry N. Abrams in association with American Folk Art Museum, 2001), 356.