[Theory] Monkey D. Dragon

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For starters the '11 'supernovas' was a specific title for the 100m+ bounties of Luffy's generation, it's not something they use on a regular basis, still I get what you are trying to say.

That he was an infamous pirate you can probably scratch too because as I recall they said in the manga that Dragon came out of the blue challenging the WG. If he really had been a notorious pirate before that, people would have known about him and it's highly unlikely he was a small pirate captain. So you can probably scratch that his noble woman was executed as why the hell would they do that? At best they would want to execute the child and him, why would they execute the noble woman? And that is in the very unlikely case he was a notorious pirate, but even then it's very doubtful as Roger was the most heinous pirate in existence for the WG, so every last trace of his blood should be eradicated, but do you think that they are executing people on a regular basis because they are related to pirates? For them to do that Dragon should have been in WB's class and then him turning on the WG wouldn't have been something that comes out of the blue, so that doesn't make any sense.

So assuming he was a pirate, they would have just ditched the kid somewhere, trying to deny its existence because it would be shameful for the woman's family.

With other words, following the flow of the manga, Dragon was never a pirate. It is far more likely that he was a marine. Considering Garp pushed both Ace and Luffy in becoming marines, it would be no more than logical he did the same with his son. Luffy got influenced by Shanks, but it's doubtful that Dragon too had someone pirate like Shanks coming around, so he had no real reason to not become a marine. Also marines become famous far more difficult than pirates considering they get into the newspapers continuously due to their crimes, but logically that does not apply to marines. So it's much easier to remain unknown to the broad public as a marine than as a pirate. Not to mention it's difficult for the marines to say to the public that the worst criminal in the world was originally a former marine and the son of a marine hero. Dragon might also intentionally never said anything about his father to avoid being seen as 'the son of a hero'. Finally Dragon's sense of justice resembles that of Garp far more than that of Luffy. Luffy just wants to fulfill his dream and hates to be considered a hero. He does the good thing when it crosses his path, but outside that he doesn't really care. Dragon really has a greater purpose and a wider perspective.

No doubt there was a specific moment in Dragon's life, some kind of realization, event or revelation that made him go against the WG. That might be connected to Luffy's mother, that might not be connected to her and if it was, it could have been countless of scenarios.
 
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