Rupert "Roo" Avery grew up in the village of Ravensburg in the Barony of Darkmoor. His father, Tom Avery, was a teamster and drunkard and his mother died during childbirth. Considered a trouble maker and mischievious by many in the town he had few friends. His best friend was Erik Von Darkmoor, a blacksmith's apprentice and the biggest boy in town. Roo was known sometimes to use his friendship with Eric as a shield when running his mouth at bigger boys in town.
Rupert must escape Ravensburg along with Eric Von Darkmoor for the murder of Stefan Von Darkmoor. They escape on foot and attempt to make their way to Krondor with the ultimate goal being to escape all the way to Kesh. Along the way the pair meet Helmut Grindle, a merchant from Krondor. Helmut is slightly impressed with Roo's ideas on becoming a merchant but cautions him that he underestimates others and their abilities. The pair is eventually captured and locked up and put on trial for the murder of Stefan Von Darkmoor. In a mock trail Roo and his friend Erik are both sentenced to death. Erik and Roo are secretly selected during their trial by Gamina, daugher of Pug, to join Calis' soldiers. Their exectuion turns out to be a mock hanging and their sentence is commuted to service in Calis Crimson Eagles. They are trained by the tyrant sergeant Robert de Loungville
After some training the entire mercenary company departs across the Endless Sea for Novindus and eventually forms the mercenary company Calis' Crimson Eagles. The mercenary company is eventually folded into the Emerald Queen's army and they subsequently escape from Novindus and return to Krondor.
Upon Roo's return to Krondor he set off with his pardon and reward money in hand from his expedition to Novindus to become a rich merchant. He journeyed back to his home town and bought a wagon and a wagon load of wine casks with the idea of selling the upscale wine at discount prices in Krondor. With help from his father, Tom and cousin, Duncan; Roo sets off to make his fortunes in Krondor. During the trip to Krondor Roo uses a small trail to avoid paying the taxes on the King's Highway and is accosted by several bandits, during the skirmish Duncan proves his worth and Tom dies from a heart attack.
Barrett's Coffee HouseEdit
Roo finally makes it to Krondor and begins to sell his wine, making a decent profit. During his day selling he runs afoul of the Mockers who try to extort some of his money. Roo refuses and later that night the Mockers steal his money, break his wagon and spills out all of his remaining stock. Now destitute Roo is forced to find employment. Roo becomes a waiter at Barrett's Coffehouse, the unofficial heart of commerce in Krondor. While at Barretts he garners respect for his quick thinking and befriends a young waiter named Jason. During his tenure at Barrett's Roo also begins a rivalry and feud with Timothy Jacoby, that will eventually lead to bloodshed.
Bitter Sea TradingEdit
With some ill gotten gains from the wagon incident in front of Barrett's Roo approaches his old acquaintance Helmut Grindle and the two begin a partnership. He works for Helmut for some months and begins to court his daughter Karli Grindle, though his designs on Karli are nothing more than to get tighter with Helmut and advance his own wealth. Helmut is killed by bandits, employed by Timothy Jacoby and Roo takes over as sole owner of Grindle and Avery traders. Roo marries Karli, though he does not love her, because he felt a debt to Helmut and feels responsible for his death because of his feud with Jacoby. Roo pours himself into his work and begins to increase his wealth and then while trading comes upon a piece of information that is too good to be true. Roo discovers that locusts have all but destroyed the wheat harvest in the west. He uses this information to form the Bitter Sea Trading and Holding Company and they leverage their wealth on buying cheap grain futures in the expectation that when word circulates that locusts have destroyed many grain crops that prices will rise. The prices do rise and during this they are able to all but ruin Timothy Jacoby and damage tycoon and rival Jacob Esterbrook. Roo becomes a very wealthy man.
With the looming invasion of the Emerald Queen, James the Duke of Krondor begins to get Roo to finance the defense of the entire western realm, much to his own dismay and his ever shrinking wealth. When the army of the Emerald Queen does land and destroys much of the western realm, especially Krondor, Roo is forced to flee with his family back to Ravensburg and eventually on to Darkmoor where the kingdom armies make their stand. The Kingdom of the Isles is in debt to Roo for millions and will most likely never pay him back. Through all his ordeals Roo returns to his humble roots as a simple merchant and through his experiences comes to truly love his wife and appreciate his role as husband and father.