At the point when Roger initially meets him all Rayleigh says about his past is that his home copied down and he took this pontoon and lives in it.
So in the manga Roger just appears, asks his name, and Rayleigh is reluctant and just says "… Rayleigh" and afterward Roger says well this is a lucky event, how'd you like to flip around the world with me?
Furthermore, that is the place where the manga flashback finishes and re-visitations of Rayleigh destroying.
Imagine a scenario where "Dim King" Rayleigh, is very exacting. The World Government didn't care for him, said he was a dim lord, presumably for not joining the World Government, and freed the realm from Rayleigh and copied his château down
So he just fled on this vessel, wanted to drink away his days realizing the World Government was pursuing him on the run, and unexpectedly Roger gave him a possibility of flipping around the world, and he figured why not? I'm going to be executed in any case eventually should turn into a Pirate with this person and annoy the World Government however much as could reasonably be expected..
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