The end of the Bracero Program in 1964 began the cycle of illegal migration across the U.S.-Mexico border, resulting in an unauthorized population ?in the shadows? of everyday American life. In 1986, Ronald Reagan, along with congress, passed the Immigration Reform and Control Act (IRCA), which stands as the most significant piece of immigration legislation since 1965. The most controversial, and extensive element of this act granted an ?amnesty? for qualifying undocumented residents residing in the United States since before 1982. Over 3 million undocumented residents gained legal residency in the United States, effectively ?wiping the slate clean? to enforce and control illegal immigration. Over twenty years later, however, the United States now has an estimated 12 million undocumented migrants within its borders, displaying the ineffectiveness of IRCA to stem the flow of illegal migration. This population works, lives, and consumes in U.S. society, while constantly at risk of arrest and possible deportation. This risk became more imperative when, after President Bush?s failure to pass the Comprehensive Immigration Reform Act in 2007, he began endorsing mass raids on workplaces, deporting thousands of undocumented workers. During President Obama?s campaign, he incurred considerable support from Latino communities in the U.S. through promising to provide ?a pathway to citizenship? for these undocumented residents, resembling the amnesty provision under IRCA. This study attempts to assess whether President Obama, in today?s economic and political atmosphere, can enact a modern-day amnesty that avoids the ineffectiveness of the IRCA legislation within his first term of Presidency.