This question has been on my mind for over 20 years and since then there have been many vert, flatland, and other technical skaters that have come and gone. Some have been incarcerated, while others have died. Those that are still around are also considered as living legends. Being a skateboarder can be a thrilling pinnacle of freedom few people can experience while society as we know it, will never accept or understand. I am certain this question will become a living debate amongst the living for the rest of time because it evolves so rapidly it's hard to imagine how skateboarding was to what it is now. We can only hope in the future, we all can look back and see who really is the greatest. But for this question, you need to look at pioneering innovation, progression, originality, and character. Other than that, it's up to you. What do you think?