In order to create a successful community on territorial Florida’s frontier – where settlers could raise families and conduct business in relative safety – leaders had to establish law and order. In Monticello, the seat of government in Jefferson County, as in other cities across the state, courthouses and jails were among the first structures built. The two-storied brick jailhouse that remains today was not the first one built in Jefferson County, but it did serve the community for most of the twentieth century. It operated as headquarters for many different sheriffs through vast political, economic, and cultural changes. It detained prisoners from the harsh days of convict leasing, through Prohibition and the Depression, to the end of legal segregation of races. As a hub of daily activity within the region, the local jail is the key to understading te history and character of the community.