The purpose of this article is to explore the role of the International Olympic Committee’s (IOC) codified marketing policy known as Rule 40 which emerged to prevent ambush marketing of its biennial events. Rule 40 has quickly evolved into a controversial rule for athletes, coaches and sponsors alike who are involved in the Olympic Movement. The IOC believes that social media is a ubiquitous threat to its intellectual property during the Olympic Games akin to traditional print and television ambush marketing campaigns. As a result, the 2016 Rio De Janeiro (Rio) Summer Olympic Games represented the most intense clash between individual, virtual free speech, expression and association versus this multi-billion-dollar enterprise’s attempt to protect its commercialized international sports monopoly from the most minute of rapscallions with a cell phone.  Part I explores the fundamentals of both Rule 40 and ambush marketing, including a broad discussion of the Lanham Act and the United States Olympic Committee (USOC). Part II provides an historical perspective on ambush marketing and Rule 40 with respect to the Olympic Games. Part III focuses on the IOC’s Rule 40 and examines its effect, impact and enforcement leading up to and including the Rio Games. Finally, Part IV provides examples of how Rule 40 invited push back from unofficial sponsors seeking relief from the courts. Whether relaxing Rule 40 further might be more practical is addressed as well particularly given that the Olympic Movement has other issues that may threaten its brand and undermine credibility in the first place, and a few suggestions are proffered as well.