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Rosinante was the younger brother of Doflamingo Donquixote. Both of them were formerly World Nobles but their father decided to leave everything behind and live a modest life among the commoners. Whole Donquixote family moved to some northern country. In the One Piece episode 702 Donquixote Homing introduced themselves to the commoners as former World Nobles but this scene One Piece manga was never shown.
After this they will for the first time ever feel the anger of the commoners. The enraged citizens blamed them for all the pain and suffering inflicted by World Nobles thus forcing them to flee. Since they lived in poverty and ungrateful conditions their mother got ill and died soon afterwards. All these events had a great impact on Doflamingo, who killed his own father at the age of 10.
Doflamingo tried to get back to Mariejois while Rosinante wandered around until he met Sengoku, the Marine Admiral, who will soon accept and enlist him into Marines. Eventually, Rosinante rose up the rank of a Commander. His Marine code was 01746. If you read it in reverse it goes like this: 6 (Ro), 4 (shi), 7 (na) and 10 (ten). This was shown in One Piece manga chapter 767 (p. 12) and in the episode 706. In the meantime, Doflamingo became a Pirate and formed the Donquixote Pirate crew.
Later on, Rosinante joined Donquixote Pirates in order to monitor Doflamingo's actions and inform Marines of their movements. He soon became a second Corazon of Donquixote Pirates thus making him a double agent. Corazon along with Trebol, Diamante and Pica are the titles given to Elite Officers. Vergo, who was the first Corazon, became an undercover Marine while serving to Donquixote Pirates, while Rosinante became an undercover Pirate while servering to Marines.
During his mission, Rosinante met a kid from the North Blue. His name was Trafalgar Law. Their story will soon become one of the most popular and saddest stories in One Piece. In the SBS, One Piece Manga Volume 79., it was confirmed by Eiichiro Oda that Rosinante hated bread just as much as Law.
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For the creation of Rosinante, Eiichiro Oda was probably inspired by the book called "El ingenioso hidalgo don Quijote de la Mancha" written by Cervantes. Don Quixote, protagonist of the story, had a horse called Rosinante, who was just as clumsy as Oda's Rosinante. The word "Rosinante" comes from a Spanish word "Rocin" used to mark low-quality horses.
Regarding his appearance, Rosinante's eye tattoo is similar to the eye tattoo of Alex from a movie called "A Clockwork Orange" from 1971. The mouth tattoo or a make-up resembles the one sported by the Joker (Doflamingo's underground codename) from "the Dark Knight" movies. Similar to Joker, who burned down a hospital, Rosinante burned one as well since they refused to help Law (One Piece chapter 764 and episode 703).
At the end of Chapter 766 (Episode 706) Rosinante wanted Law to remember him smiling if he ever thought about him in the future, therefore this is the most likely the origin for the smile on the Jolly Roger of the Heart Pirates. Eiichiro Oda skipped one week and released the chapter the week after in order to honor Masashi Kishimoto and his manga since the last chapter of Naruto was about to be released on Nov. 7. 2014..
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