I went into more detail in many of my theories why I think that Gol D. Roger and Monkey D. Dragon met but I haven’t mentioned IMO the best arguments yet.
Their meeting is essential in understanding Dragon’s character motivations and the mysteries surrounding him. Without further a do, let’s go!
Outside out of Roger’s adventures we know about the aftermath that his rise to Pirate King has brought with it. I am talking about the execution of everyone who supported him on his journey and of course, the killing of any lover and potential child of his.
Roger was aware that the Government will trace his steps back and kill any lover and offspring of his. “Coincidentally” there is a character who appeared out of “nowhere” and covered his tracks. It is the mystery man himself, Monkey D. Dragon.
Not even his own crew members(except one) knew his real name and where he originated from. I think the most likely scenario is that Dragon came to save Roger right before his execution(4 am or something), in an attempt to save him. We even know that he was physically there that day, though Dragon didn’t knew(because the Government didn’t made it public) that Roger wasn’t captured but was willingly giving his life to create a new era. From Roger’s perspective this is a positive surprise and he is glad to meet a person like Dragon.
Roger is willing to sacrifice his own life to create a generation in which the “Will of D” is fulfilled. Then a “D” comes to save him and not just some guy, GARP’S SON(right after/before Roger and Garp had their talk), who is a “D” and has a will for freedom like Luffy. I don’t think I have to tell you how Roger would believe this was a “fateful encounter”.
Dragon showed him a conviction similar to his and is willing to share his knowledge about the deepest lore of One Piece.
There is already precedent that Roger was willing to tell important people like Whitebeard the truth about the “D”. What would he do if he encounters a person who might actually be the one he is waited for? I think that Roger told him enough so he knows what is wrong with this world.
Roger tells him about the mentality of the “night” which is to discard people, where the “dawn” believes that those people deserve a place.
Roger told Dragon the literal “Will of D” and this is why Dragon remembers Roger’s words in his introduction, he heard it from him personally and is even responding to them. Though he also tells him the risks involved if he wants to change the world. Dragon isn’t allowed to use his real name and has to cover his tracks. Otherwise, the people who he loves might find their demise and that Dragon shouldn’t make the same mistake Roger did.
That is the reason why Dragon isn’t together with Luffy and his wife. Dragon knew if he wanted to change the World he had to lose his background and close relationships, otherwise they might find the same ending that Roger’s offspring found. That is why he made a decision that day, which is to cover his tracks and make sure that nobody knew where he came from.
As a demonstration of his convictions to change the World he puts “war paint” on his face, to show himself and others that this is the path he has chosen.
*Theory by Donal D. Trump
