Jefferson Monroe Levy was a three-term U.S. Congressman from New York, a leader of the New York Democratic Party, and a renowned real estate and stock speculator.

Monticello was the primary plantation of Thomas Jefferson, a Founding Father, author of the Declaration of Independence, and the third president of the United States, who began designing Monticello after inheriting land from his father at age 14. Located just outside Charlottesville, Virginia, in the Piedmont region, the plantation was originally 5,000 acres (20 km2), with Jefferson using the forced labor of Black slaves for extensive cultivation of tobacco and mixed crops, later shifting from tobacco cultivation to wheat in response to changing markets. Due to its architectural and historic significance, the property has been designated a National Historic Landmark. In 1987, Monticello and the nearby University of Virginia, also designed by Jefferson, were together designated a UNESCO World Heritage Site. The current nickel, a United States coin, features a depiction of Monticello on its reverse side.