United States President Barack Obama issued an Executive order on November 20, 2014 to implement new law regarding the American immigration system and deportations. The system has long been skewed, and a polarizing issue among both the general public and of those involved in the United States government. Obama, by issuing this decree, created a law on his own due to congressional deadlock in creating and passing immigration reform legislation. However, the constitutionality of his decision to do so has now become highly debated, with many officials and academics across the country asserting their beliefs in his legal ability to issue the order. The ability to create laws is explicitly prescribed to the Legislative branch in the Constitution, but there have been past examples of Executive authority being necessary so as to preserve the Union and allow the government to continue. This thesis will examine the constitutionality of Obama’s Executive decree and the potential precedent that it will set for future Presidents by analyzing it within the context of John Locke, the original proprietor for the rule of law, James Madison, the father of the United States Constitution and separation of powers system, Alexander Hamilton, the forthcoming advocate for an energetic Executive of the Founding Fathers, the Abraham Lincoln presidency, which involved the crisis known as the Civil War, and the George W. Bush presidency, widely known as one of the most polarizing constitutional presidencies in American history. When looking at these past examples it becomes clear that Barack Obama overstepped his place in the government with no existential crisis threatening the nation, therefore setting a dangerous precedent for future Executive’s as well as damaging the force of the separation of powers system.