Don comes from a prominent Plistian family, most of the wealth of which comes from publishing. His clan owns and operates the oldest publishing company in Plist, "Board Books," which was established in 501, just a year after the village was founded. Several of Don's ancestors, who founded the company, had been printers in Pritt, which is famous as the birthplace of the printing press, in 390. (While Don's ancestors were not among the original founders of Plist, they were among the earliest immigrants to the village after it was settled.) In 505, the company developed a more modern printing press which could more easily print pages including both text and images.
Don's parents, of course, provided him with the best masters to educate him in various subjects, all of which he excelled at. However, not all of his time was spent studying, and he spent as little of his free time as he could with the children of other wealthy clans (though he was quite capable of conducting himself with flawless manners, when in high class company). He preferred spending his time having fun, and he found that most of the children who shared the same idea of fun that he did were from less affluent clans. In fact, one of his very best friends was Palzo, who came from a clan that harvested trees and provided lumber to a local saw/pulp/paper mill complex from which Don's clan obtained paper for their publishing company.
While Don had a great interest in reading (particularly history books and works of historical fiction), he had no interest in taking a job in the family business. His parents assumed he'd eventually change his mind, or at least sooner or later find a suitable occupation of some other type. However, his love of fun, and of hanging with what his parents deemed "the wrong crowd," led to his joining a local street gang called the Chieftains when he was 15, in 889. Don himself never expected to stay with the gang for long, but he found it quite enjoyable while it lasted, and in his own words, "just sort of never got around to quitting." In those days, there was little if any organization within gangs, and Don, as was the case with many young gangsters, never had an official position. He was equally adept at the sort of roles which in later years would be classified as spy, thief, dealer, and enforcer. He might even be said to have performed the sort of functions which would later be done by "Adults," though at the time no one had any real concept of such a role, let alone such a job title. By the time he turned 20 in 894, he was one of only three members of the Chieftains still around from the time he'd first joined the gang, the other two being its leader, Chas, and a spy named Damien. Everyone else who'd joined around the same time as them had by now left, and been replaced by other, younger gangsters. Chas himself felt he was getting too old for such shenanigans (being 23), and he too departed. It was the opinion of both Chas and Damien, as well as the younger gangsters, that Don should become the new leader, a position which he accepted with mixed feelings. He was of course grateful for the trust everyone had in his abilities, but he felt he was also getting too old for this life. He wanted to find a real job, and make his parents proud. And certainly, he had plenty of potential to do whatever he wanted in life. So, he said he'd take the position until such time as either a suitable replacement emerged (since he didn't want to leave his gang in the lurch), or until he finally figured out what he truly wanted to do with his life.
Apparently, he either never figured that out, or else figured out that this was the life he wanted, after all. He continued enjoying his gang activities, and enjoyed the friendship of many of those he worked with (three years after becoming the Chieftains' new leader, he hired his old friend Palzo as a spy). Under Don's leadership, the Chieftains became the most prominent gang in Plist. By the time he was contacted in 899 by Capp of Kimrin about forming a new inter-village gang called LandOrder, there was really only one other gang in Plist that even came close to rivaling the Chieftains: the Greys, which was at the time led by Seth. That gang soon became one of the founding members of InterGang, while the Chieftains became one of the original gangs in LandOrder. Little is known about the talks that went on in 899, between the various gang leaders who formed LandOrder, but it is said that the position of a village's gang leader was given the new title of "don" in honor of Don, while the position of an inter-village gang's leader was given the title "capo" in honor of Capp. (These terms are understood to also be subwords from Earth for crime bosses in the Mafia, which is one word for organized crime on that world; though the precise usage of the terms by Terrans is not fully understood by Landians, and it is said by some that our world's gangsters might even have it backwards.) The fact that Don's name is the same as his title has sometimes led to a certain degree of confusion concerning what people mean when they refer to him as 'Don Chieftain,' though it is still almost unheard of to refer to him as 'don Don Chieftain,' basically because everyone seems to agree that would sound just silly.
When the surname law was passed in 904, Don chose the name Chieftain, in honor of his gang (which was then simply known as the "Plist branch of LandOrder"). Though many claim it refers not just to his old gang, but to the fact that he personally is the "chief" of that gang. Still others claim that it is in honor of his clan, who he continues to consider "chieftains" in their own right, even if his choice of career has made it impossible for him to associate with them. This belief is somewhat disputed by some, who claim there is bad blood between Don and his family because of certain disagreements during the Coming of the Order, though these claims are the subject of debate.
Don Chieftain remains a greatly respected member of LandOrder, and is recognized even by members of InterGang (which oddly adopted the terms "don" and "capo" for their own rank system, as well) as being one of the most capable leaders in any gang on the Land. In spite of his reputation as a brilliant leader, he is also well known for following his own hobbies, such as his old interest in history, as well as the aftermath of historic events such as the Coming. It is this very interest which led him to have his spies keep tabs on Darius Lonewander, the son of Adam of Triscot, one of the Protestant Movement's leaders during the war. This interest eventually led, in 912, to a temporary alliance with the rebellion against the Second Order, which was started by Darius. However, following the Chaos War that year, various factors apparently led to a dissolution of that alliance....