Warning: This entry contains major spoilers for plot for the first game of the Trails series, along with spoilers for scenes in the second and third games that reveal his backstory. No plot spoilers beyond the ending of the first game. This also will contain parts from the Loewe gaiden manga and drama CDs that fill in more pieces of backstory and are considered canon (and have been kindly translated by Misa).
Note: Anything before about spring 1192 by their calendar (basically around the event known as the Tragedy of Hemel) is pretty much pure headcanon. Canon doesn't say anything one way or another, but does back up my likely guess for when he was born at least.
Born in 1176, about the best estimate is late winter or early spring. He honestly doesn't even remember what his actual birthday is and what he uses for it is a day he made up that is supposedly close (it's actually the day he met Karin). He was orphaned at a pretty young age and doesn't remember his parents at all. About all he remembers was that they were going somewhere and monsters attacked and he was told to run away and find a place to hide. He was found later just outside the village of Hemel by a beautiful young girl with black hair. One thing that will always stick out in his mind was that at first he thought the girl an angel. But then he was about half dead from thirst and exhaustion and she was the first human being he'd seen.
Since no one could find any family of his, he was told he could stay as long as he wanted. There weren't many other children in the village, in fact the only other one was the girl who found him, who he found out was called Karin (note: canon does confirm the lack of children in Hemel, Leonhardt, Karin and Joshua were the only ones). No particular family adopted him, but nearly all the adults made sure he was taken care of, pretty much the whole village became his new family, a big part of why the village being destroyed later hurt so much. And to him Karin was not only like a sister, but also his best friend and the person he liked the most. They of course made childish promises to get married when they grew up and fill the village with children. To him those were just the best days of his life, just full of happiness and life was simple. He and Karin would play together after finishing their work around the village and she'd play the harmonica for him every day.
Time passes and when he was 10, Joshua was born. Karin doted on her new little brother and Leonhardt also adored the little boy. Even though they were still young, they did their fair share to help raise him and since the two of them were the only other children, they also played with him. Leonhardt grew to think of Joshua like his own little brother too. As the years went past he grew more serious with Karin and those childish promises became more serious promises. Once they were old enough, they planned to marry, and Joshua would live with the two of them until he was old enough to move out and start his own family. He trained in using a sword in the style of the men of the village so he could protect her and Joshua and made plans to become a bracer when he was old enough to pass the test to qualify (this can be taken after a child has turned 16 and shows enough skill to pass training and take the test, which is basically being able to complete a test job, FC shows Joshua and Estelle's own test). He didn't want any other children to be like him or for any parents to have to die for the sake of their children being able to survive. Joshua definitely supported this idea (but then, Joshua is totally a fanboy of his), but Karin wasn't nearly as supportive. Her concerns were for his safety, and then also who would protect them when he was gone. Of course he swore to always make sure she and Joshua were safe.
Sadly, the very next day tragedy struck and the village was attacked. Leonhardt helped defend off the attackers with the other men of the village while the women and Joshua tried to make their escape. Unfortunately their attackers cared little for who they killed and even the women found themselves victims. And their attackers were definitely the foulest of the foul and even brutally raped the women before killing them. Before he went to help defend the village, he sent Karin and Joshua off to escape and said he'd meet them later.
Unfortunately, Karin and Joshua weren't able to escape as they met up with a soldier. Karin did her best to try and defend herself and Joshua from attack, but she was definitely not capable of fighting. The best she really could do was use herself as a shield for Joshua. Unfortunately when the soldier shot her in the leg Joshua just froze up and couldn't do anything, not even run.
Leonhardt eventually caught up with the two of them, but he was too late to save Karin and she died in his arms after giving Joshua the harmonica she had so lovingly played for the two of them, asking Leonhardt to support Joshua and thanking him for everything.
And at this point, his life changes completely from one that was overall pretty normal and happy, to one of complete and utter misery. Leonhardt and Joshua were the only two to survive the tragedy. It was now up to Leonhardt to not only support Joshua, but to basically be his sole caregiver. True, he'd done much to raise Joshua so far, but now he was having to act as father and brother, and Joshua had completely broken due to what he had seen that day. And really, Leonhardt wasn't much better off.
The day after it, they met a strange person by the name of Campanella. It wasn't very long after meeting Campanella that Leonhardt ended up joining a society by the name of Ouroboros. Between what he learned from Campanella, and the promise made by one George Weissmann to restore Joshua back to what he had been before, Leonhardt just couldn't resist it. They needed somewhere to go, the soldiers were after the lone two survivors to erase them so they could not talk about what happened and it was not only the best choice, it really seemed to be the only choice available to them.
Leonhardt quickly worked his way up to being an Enforcer within the Society and earned his current position as Legion no. 2 and his title of The Sword Emperor. Eventually Joshua ended up joining with him, starting first with helping out on missions and then being trained by Leonhardt personally. He eventually worked his own way into an Enforcer position as well, and while still a young child at that.
However, one big thing to understand is that Weissmann isn't exactly the nice person he seemed to be when Leonhardt joined up with the society. Yes, Joshua was fixed, but at the same time, he was no longer exactly a normal boy. He lost all fear and hesitation and was basically becoming a human weapon. Yet when Leonhardt approached Weissmann about this, it did very little good. He'd get responses just basically saying that that was what training was for and even insulted.
So he just concentrated on training Joshua to ensure the boy remained safe and they often went on missions together. As the years went by the two of them were joined by the other enforcers we meet later in SC and eventually they end up rescuing a little girl named Renne who the two of them adopt as a little sister and she also joins up with the society. When Renne joins them, Joshua actually starts acting almost human again around her and they start having something resembling a normal life as a normal little family with the three of them in between performing missions, of course. Renne is definitely an odd child, but truly, that doesn't change the fact that Leonhardt adores her. Seriously, he's just really good with children, and especially the orphans who are not exactly normal children.