The 20-year anniversary of the North American Free Trade Agreement (NAFTA) has been seen as another milestone in the ongoing trade relations among Mexico, Canada and the United States. It offers a good opportunity to assess how the agreement has worked and to consider whether regional integration can be enhanced. There are many ways to evaluate NAFTA. This paper undertakes a stratified analysis, while considering each party’s perspective. Such an approach places NAFTA in its historical context while also looking forward, in order to reflect on whether a fuller integration can be achieved to assist the three parties in facing the significant global challenges of today.