In Chapter 0, during Roger’s execution, we see several notorious pirates present in Loguetown like Shanks, Buggy, Doflamingo, Mihawk, Moria, Crocodile.
We also see the infamous Monkey D. Dragon before he gets a tattoo.
Why would he have any interest in executing the Pirate King? He is the only one to have a rather concerned and serious look in the board. (You could say Mihawk too, but Mihawk just seems to be watching).
Along with Buggy and Shanks, he’s the only one who seems a bit worried or sad about the execution. He’s not completely crying or sobbing like Shanks or Buggy, but it’s almost as if he’s worried or – at least – understands, to some extent, why Roger chose to be executed.
Is it possible that he spoke to Roger at some point before his execution? Maybe Roger recognized him as Garp’s son and a member of the D.
We think Roger and Dragon definitely met. We believe that Roger was able to talk a little about the history of the World and the Poneglyphs with Dragon – seeing as he had great faith in Garp and was also a D. After the execution, we believe that Dragon came up with the idea to create the Revolutionary Army.
Dragon has a very good sense of justice, as we saw in the FSA flashback when he notices that Sabo thinks like him about the status of nobles and how society works.
In Vivi’s flashback, we saw that Dragon was just beginning to be recognized as a threat to the World Government, so he couldn’t be a Revolutionary at the time of Roger’s execution.
In Chapter 100, as Luffy is spared Buggy’s execution, we see Dragon engage in a rather badass self-monologue.
“What cannot be stopped: the inherited will, a man’s dream, and the flow of time. As long as a man continues to seek the answers to freedom, these things will never be stopped” – These are the words of Gol D. Roger. We believe Roger said those words DIRECTLY to Dragon, before saying them to the audience during his performance.
-Inherited Will: It seems to us that Roger may have spoken to Dragon of the line of D. Just like he told Whitebeard about it.
-One Man’s Dream: We believe this is a reference to what Roger’s Pirates learned about the ancient kingdom and the will of their leader – Joy Boy.
-The flow of time: 800 years have passed since the fall of the Old Kingdom and the end of the Age of the Void – only time will put these things in motion.
While we don’t think Dragon knew the entire Void Age the way Roger, Rayleigh, Scopper Gaban and the others did, we do think Dragon’s learning of the Will of D. put him on the map. mission to overthrow the World Government and their injustice to bring it True Justice and Freedom.
This is why Dragon got Shandian-like tattoos tattooed on his face – perhaps as a sign of his ancestry with Clan D. and the Old Kingdom – as we know that the Shandian were, at the very least, allies of Joy Boy and the Ancient Kingdom.