Executive orders are legally-binding proclamations issued by Presidents in their own independent capacity as executor of the nation's laws. Despite there being no mention of these orders in the Constitution, they have been implemented since Washington's presidency, with some Presidents issuing over a thousand. Many contemporary legal scholars fear that this practice has gotten out of control over the past 80 years or so, resulting in an inappropriate usurping of Congress' legislative power by the executive branch. In this essay, I will use a chronology of executive orders from across the relevant time period to assess the historical validity of this claim. Additionally, I will use federal court decisions that have overturned executive orders to examine whether anything unconstitutional or otherwise legally improper has taken place over the time period in question. Ultimately, I will conclude that while the legislative authority wielded by the executive branch has grown, this expansion has adequate legal justification and political safeguards until such time that the judiciary provides more robust guidelines.