Upon joining the academy Osbert proved his worth rather quickly. He was instructed to kill another student when he was only seven and he obeyed without crying or complaint. In time he came close to Proctor Temur and began to view the proctor as a second father of sorts.

After undergoing the harsh realities of the academy he found himself graduating as a Second Level Dreadlord pledged to work with House Banick. He came to love his life of splendor sipping on fancy wines and dining on succulent pork inbetween the missions he found rather routine compared to academy life. This short lived vacation came to a screeching halt once the revolution of Vel Anir began.

In a matter of weeks his House had sued for peace with the revolutionaries, Proctor Temur died defending a nation that no longer existed, and Osbert was being asked to live out the rest of his life eating military rations and sleeping on the dirt. The nation that had stolen his entire life was now offering him the choice of more misery or exile.

He chose exile. But not before convincing several of his disenfranchised Dreadlord acquaintances to jump ship with him. They made their way to Syzemore, a city on the coast south of Alliria, and planned to live a life of luxury with or without the aid of the so-called "Noble Houses."