Jonathan Quincey Goatleaf was born in the year 1665 of the Bree Reckoning in a large, two-family house on the Great East Road on the east side of Bree Proper. His parents, Mister and Missus Timothy and Eliza Goatleaf (Eliza born to the Baker family) were simple folk: Tim was a guard (as many Goatleafs are) and Eliza was a typical housewife.
Jon had quite a few friends about town. There was Robby Blueoak, Barney Butterbur, and and the Longholes twins. He was on friendly terms with most of his relations, and especially close to his cousins Gareth, Samuel, and Frieda. He had a couple of cousins who worked as constables, the brothers Harry and Ned, but he was never very close to them at all. However, Jon's relationship with his cousin Sean wasn't quite as healthy as will be seen.
When he was five years old Tim sent Jon to school for the first time. He was not a very shy boy and made many more friends (most notably was young Foldo Brockhouse, a hobbit from Archet; Jon was very sad when his family removed to Scary in the Shire), but his academic skills left something to be desired. In the end all the boy got out of the experience was basic reading skills and a fundamental understanding of arithmetic.
Jon left school at the age of ten to work as a farmhand in the hobbit-village of Staddle. He would make a daily trip around Bree Hill to the pipeweed fields of the Overhill family, work all day, and return home to Bree with his day's pay. He learned a great deal about tobacco, and came to appreciate in particular Longbottom Leaf, a variety grown in the Southfarthing of the Shire.
At the age of twenty Jon left his job at Staddle to persue a career closer to home. After a few months working at the Prancing Pony Inn he became the third assistant to the second janitor of the Northlands Bank. It was a thankless job and it paid terribly, but since many wealthy patrons were liable to drop loose change on the floor, Jon really didn't mind.
The job at the bank lasted five years. Unfortunately for Jon, who had recently been bumped up to second assistant, his aforementioned troubles with his cousin Sean came into play. Sean, jealous of his cousin's 'high position' (Sean had worked as a constable all his life and considered Jon's janitor bit a life of luxury), came to Jon one day itching for a fight. Jon was given twenty-five hours to either fight or leave town. Naturally, he did just what any red-blooded Breelander would do. He was halfway to Combe by midnight.
Sean made sure Jon never came back to live in Bree. The first thing he did was purchase Jon's house and sell his parents provisions for a one-way trip to Dunland (they're believed still to live a pleasant, comfortable life on a farmstead just outside Kierkgard). Once this was done Sean purchased a rather unpleasant large dog that he kept outside his new home in case Jon had any ideas about returning. Finally, he sent a threatening letter to Jon informing him that if he ever even thought about confronting him he'd have every constable in the Bree-land after him for attempted murder (Sean could do it: he had very close ties to his boss -- and his boss' wife).
Jon was in a pickle. He couldn't return to the meager existance in Bree without having his face disfigured, so he sent a polite letter to his former employers explaining that for reasons of his own he could not return to the bank. In return he was given a notice that he would never work in Bree Proper again (it seems Sean was also rather close to the bank owner's wife). And so, with what he had learned in the Staddle fields, Jon decided that farming was the best thing for him.
And so, with the money he had from the bank and the aid of the now wealthy Longholes (they had found a box of fine wines sealed in their basement by an ancestor and became rich selling them) Jon purchased a few acres outside Combe. There he grew vegetables, mostly radishes, and profited selling them to folks passing through Combe.
When he was twenty-eight Jon met Arkaeth, a young ranger who had decided the adventurous lifestyle of his fellows was not for him. He had settled in Archet a few years earlier and set up a small general store. Jon and Arkaeth met when Goatleaf was visiting Foldo Brockhouse, who had in turn returned to the Bree-land to visit his grandparents. The three became close friends, though Jon and Foldo laughed at Arkaeth's silly stories about rangering.
At the age of thiry-four Jon met Rosie Appledore, a local woman who had lived all her life with her family, helping her impoverished parents out by knitting blankets and sweaters to sell to travelers. It was love at first sight. After courting for about a year, the two were married by the Mayor of Bree at the town hall. When they were married for four years Rosie gave birth to a son, Jonathan Q. Goatleaf, Junior.
In 1720 Jon made two quick trips to the Shire. On the first he accompanied a group of travelling musicians upon the request of his wealthy cousin Arliss. On the second he met a tradeshobbit named Reginald Bolger, who was very nice to him. However, after bumping his head on the roof of the Green Dragon Inn in Bywater he decided not to come back to the Shire.
In 1721 Jon began to make routine trips into Bree's market to sell his wares, ever watchful of Sean. There he met Rashi Findling, the bookkeeper at the Prancing Pony, a stuffy fellow who often insulted his vegetables (especially his radishes), much to Jon's ire. He also met Niebel Bushroot, an intense hobbit with an extreme dislike for drunkards, and vowed never to get drunk in Bree again for fear of suffering the wrath of Bushroot.
A few weeks later Jon met an odd fellow named L'mar. He was there visiting 'a friend of the family', and was staying at the Pony. He was an odd man, and reacted very strangely to pipe smoke. He soon left the inn with a lady friend, and Jon dismissed the rather queer matter for the time being.
One day Jon met a wizened old man in grey robes at the Prancing Pony. Upon asking the man's friend, a hobbit named Farod Overhill (a relative of Jon's former employers in Staddle, it would seem) for a bit of his new, experimental variety called 'Dragon's Nest', this man warned him that it was a particularly strong variety. Later on, Jon learned that the man was Gandalf, an eccentric gaffer who deals in fireworks.
Jon still lives in a little farmhouse outside Combe with his wife and son, making occasional trips to Bree's market and inn.
(Note: the last four paragraphs, excluding the short fourth, are from actual RP. The fifth paragraph from the last is based on an occasion on which I temp-alted in the Shirefolk culture. L'mar is a former Yfelwydan human currently Olfo and the 'lady friend' is Aislin, currently Frodo.)