Just before his death, it seems that D' starts to find a different kind of "freedom," finally able to develop new habits precisely because there is a change in habitat. Through his engagement with literature, turning to, of all possible novels, the pseudo-aristocratic world of Fitzgerald and his Gatsby, D' starts to open new horizons of possibility as to what it means to be "free." What does the West Egg of the 1920s have to say to the Baltimore of the 21st Century? How does Gatsby speak to the D'Angelo?
He's saying' that the past is always with us, that where we come from, what we go through, how we go through it. All this shit matters…Like at the end of the book, boats and tides and all, it's like you can change up, right, you can say you somebody new, you can give yourself a whole new story, but what came first is who you really are and what happened before is what really happened and it don't matter that some fool say he different, what makes you different is what you really do, or what you really go through. like, you know, all them books in his library. Now, he frontin' with all them books, but if we pull one of the shelf, ain't none of the pages ever been open. He got all them books, and he ain't read ne'er one of 'em. Gatbsy, he was who he was. and he did what he did. and cuz he wasn't ready to get real with the story, that shit caught up to him ("All Prologue", Season 2, Ep. 6).