Let me start off by saying that I, like almost 10 million other people, am a fan of Casey Neistat and his daily vlogs. Casey’s style, creativity and storytelling ability are second to none and his videos are highly entertaining. However, the videos are also very controversial when it comes to his use of drones. Yesterday, Casey uploaded his latest video in which he buys a DJI Inspire 2 and Zenmuse X5S (?). Together with his good friends and drone experts, Elaine and Justin, they get on a boat to fly and test the new drone. The group ventures out on to the Hudson River, East River, and in the New York Harbor and capture amazing drone footage of the Brooklyn Bridge and the Statue of Liberty. Within the first 24 hours of posting the video, it has been watched almost 900,000 times and a discussion has ignited in the comments section as to whether this video constitutes legal or illegal drone flying. First of all, I am not a drone/aviation lawyer, but after having watched the video a couple of times, there are a few moments that question the legality of the drone operation and at the same time show the complexity around the FAA’s drone regulations. Let’s take a closer look.