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A round-table discussion among former U.S. Vice President Richard B. Cheney, Caruso Family Professor of Law and retired U.S. Ambassador Douglas Kmiec, and former U.S. Attorney General Edwin Meese III considered the practical implications of conceiving the Vice President as a legislative officer, an executive officer, or both. It was noted that until the second half of the twentieth century, the Office of the Vice President was conceived as legislative. Funding for the Office appeared in budget lines relating to Congress and physically, the Vice President’s office was in the Capitol. Beginning with Walter Mondale’s service as Vice President, presidents have been delegating increasing executive authority, seeing the Vice President as a “deputy president.” Perhaps the most aggressive and influential of the modern “deputy presidents” was Vice President Cheney himself. Attorney General Meese concurred and saw this as positive. Ambassador Kmiec was less approving, encouraging Vice President Cheney and Attorney General Meese to contemplate the benefits that a dual-natured legislative–executive Vice President supplies to maintaining a workable government. The capacity of the Vice President to assert independence, as late Justice Scalia explained in an Office of Legal Counsel opinion, is unique. Unlike members of the Cabinet, the Vice President is not removable by the President, and thus, the Vice President can use his dual nature to advance executive–legislative compromise. Vice President Cheney’s reliance upon his significant, but personal, legislative experience prior to his vice presidency to facilitate executive–legislative bargaining suggests qualities that presidential nominees might consider more directly in vice presidential selection, and not just geographic complementarity and ideological compatibility. While it has been commonplace to think of the vice presidential office as “an afterthought” borrowed from state charters at the time of the founding, this dialogue suggests how a vice president with a foot in each of the Legislative and Executive Branches can assist in overcoming dysfunctional periods when partisan division is great.