Now that we have the technology and trade agreements to facilitate border-free trades, why not using them. So far, the only major obstacle to the advent of smart contracts is a lack of a legal framework. It is no surprise that the legal structures to regulate the manner in which society utilizes new technologies always lag behind the technologies themselves. The regulatory issues surrounding the advent of online gambling or the distribution of digitized music are good examples. Historically, the agencies tasked with protecting consumers concerning securities and overseeing currency have been slow-footed to catch up to the workings of this complex technology. There have been some early attempts at legislation. Rep. Warren Davidson (R-Ohio), introduced the Token Taxonomy Act in 2018, updating it in April 2019. Early versions of the massive bailout legislation to deal with the COVID-19 pandemic included some forms of a digital dollar to quicken the government aid to the non-banked. In conclusion, AI, smart contracts, cryptocurrencies, and blockchain technologies are no different on the regulatory front. Instead of blocking, it is time to utilize these technologies, to facilitate our across-border trades. Maybe it is time to draft a state-less law to regulate border-free trades in our new mercantile community. At the time of NAFTA’s negotiation, the world appeared to be dividing into regional trading groups like the European Union (EU) and MERCOSUR.10 While global trade talks through the General Agreement on Tariffs and Trade (GATT) Uruguay Round were faltering (1993), the successful conclusion of the Uruguay Round trade negotiations was in peril.11 In fact, other regional agreements grew stronger as the Doha Round of World Trade Organization (WTO), launched in 2001, failed to conclude with an agreement. This Paper analyzes the evolution of trade rules for digital commerce across the North American marketplace, specifically trades governed by the United States-Mexico-Canada Agreement. It explores the manner in which NAFTA treated Intellectual Property (IP) and how USMCA introduced new chapters to protect IP and digital trade data while facilitating digital commerce. Part II explores the history of IP rights protection.