In the mid-1960s, the United States Congress passed two laws that would reshape the course of the history of the United States: the Civil Rights Act (CRA) of 1964 and the Voting Rights Act (VRA) of 1965. Passed at the height of the Cold War, these laws would be the first major steps toward bringing a close to the civil rights movement. These laws proved to be incredibly divisive for both Republicans and Democrats, but one Republican, Senator Norris Cotton of New Hampshire, stands out. In an analysis of Cotton’s votes against the CRA and then for the VRA, I examine several factors that led President Johnson to push for the passage of both laws, a series of Senator Cotton’s personal records, and Cotton’s memoirs in an attempt to uncover the reasoning behind his two conflicting votes. My analysis includes a specific focus on the pragmatic nature of Cotton’s voting decisions.