There are a number of ways for the president to persuade Congress to support his position on policies. But when cooperation gives way to conflict, the veto is often invoked. Veto authority of the chief executive has been referred to as “the most important of powers connecting the national executive with the legislature” [1] and one of the “unique American contributions to the theory and practice of government.” [2] How is it that successive U.S. presidents of different backgrounds, political parties, and legislative approaches ended up with similar records in vetoing bills they opposed? This research endeavors to address that question. The paper examines the presidencies of Harry S Truman and Dwight D. Eisenhower and how the aforementioned distinctions nonetheless led to parallels in veto behavior. The study assesses the number and type of vetoes issued by Truman and Eisenhower and compares their respective records to other presidents over American history. It also evaluates why President Eisenhower had more success than President Truman in sustaining vetoes.