Charles came from a family of woodsmen, who had provided the majority of the lumber and firewood used in Triscot, ever since the village's founding in 771. Over the years since then, the clan steadily increased its business. While they had started as laborers, by the time of Charles's birth, they had become one of Triscot's wealthier clans, though not quite among the wealthiest in the village. It's because of their woodcutting and distribution business that they chose the surname "Woodman" in 904.
In 897, at the age of 26, Charles was among the settlers of Near Port. He went there specifically to extend his clan's business to the new village, quickly establishing logging operations in the nearby forest of Kizin Wood. At the time, he had no idea that the founding of the Near Port was actually part of The Plan, and one of the earliest aspects of the Coming of the Order. However, many people within the new village soon learned the truth, and as one of Near Port's most prominent citizens, Charles himself became deeply involved in the Coming. He had hopes of becoming powerful in the government which was to be established, rather than merely in the business world. To that end, he not only supplied discounted lumber to help in the building of ships and military facilities, he also joined the Army that was being raised in 901. He was given the rank of captain, serving under major Tovan. After the Second Order was established, Charles was promoted to colonel, in charge of Near Port's regiment (while Tovan became general of the Army).
Many who knew Charles were surprised when he didn't run for any political office in 904, but chose instead to remain in the Army. It was a prestigious position, but not something he'd previously given any indication of wanting to make a career of. However, in 912, it would be revealed that he had become a member of The Cabal either during or immediately after the war of 903, which apparently provided him more clandestine power than he would have had as a politician. It is believed that he still hoped to obtain political office someday, though he had been content to do whatever was in the interests of the Cabal, for the time being. His illegal imprisonment of The Chaos for a few months in 912, and his public announcement of their capture, led to the enactment of the Counter-insurgency Act. This, and other of his actions, were largely responsible for the start of the Chaos War, later that year. But after his side lost the war, Charles was convicted of various crimes, including violations of the Prohibition of Off-world Technology and the Declaration of Amnesty. He was succeeded as commander of the Near Port regiment by Rolf Redemption.