Born with a curse, as prince's often are, Charles is sent to live in an Abbey under the care of the Friars Tuck. Taking the name as well, Tuck grows up to be expelled from the order and join his guardians in Robin's band of Merry Men.
But royal birth is not something one can leave behind and Charles is forced to return to his parents. And the curse has not forgotten him as the moment he tries to take his throne, it turns him from a prince into a princess. Unable to find a way to break the curse, Charles seems doomed to live his life now as the Princess Charlotte.
When word reaches Robin and his men that the castle is being besieged by Prince Aragon for the hand of the princess with the help of two giants, the Friars Tuck urge them to assist. So, Robin Hood, Little John and Will Scarlet set forth and defeat the giants. The King offers the princess' hand to the rescuer of her choosing and she chooses Will, who does not know the true identity of his bride.
The two are married and are soon expecting. Where the birth of the child would break the curse, turning Charlotte back into Charles, the Evil Queen's curse takes over the land before the child can be born, leaving the curse unbroken.
In Storybrooke, Charles, though no one knows that's his real first name as he just goes by Trip, Tucker is the town drunk with the southern accent. In truth, he's one of the town handy men and youth pastor, but if he can't be found on a job or at the church helping his adopted guardians Felix and Leo, he's at the bar with a beer in his hand. But even when he's drinking, he's willing to lend an ear and offer friendly advice with a smile, as he's really not one to preach.
He works with children because he has a sense of lose that he knows has to do with a child, but he doesn't know why. He fixes things because it gives him control that he feels he lacks otherwise in his life. He drinks because his sense of self is even more muddied then most people's in Storybrooke. His unhappy ending is at the bottom of a bottle.