Montgomery comes from a family that has always been devout followers of The Order, and the clan has even produced a number of spirit-talkers, over the years. (Though Monty isn't himself a spirit-talker, his mother, Violet, is the Orthodox bishop of Plist). During the Coming of the Order in 903, Monty joined the Army, as he strongly desired to fight the Protestant Movement. He felt a certain degree of shame that the Movement had begun in his home village, and more so that he had once respected its founder, Bishop Therman. He distinguished himself a number of times during the war, rising to the rank of captain. After the war, when the Army officially established a permanent regiment in Plist, Montgomery was promoted to the newly implemented rank of colonel, and was given command of the regiment.
In 912, he was one of only two colonels (the other being Stavros Supprus) to fight on the side of Poss Primus in the Chaos War. He felt that Demos Royal and The Cabal had betrayed the ideals of both the Order and the Second Order, and strongly desired to prove that one could remain loyal to both the religion and the country, while still refusing to follow the orders given by those who claimed to be acting in the interests of the country, if one believed those orders to be wrong.
After the Secession Referendum of 913 established the United Villages of the Chaos, he thought long and hard about whether to move to another village, in order to remain in the Second Order, or to remain in Plist, and accept the new country as his home. He finally decided that regardless of nation, Plist was his home, and had been his clan's home for generations. He believed that it was more important to be loyal to his religious convictions than to any worldly government, and he strongly desired to maintain an orthodox presence in his home village, rather than let Plist or the UVC come to be seen as purely Protestant in its citizenry. And so, he became commander of the Plist regiment of the Chaos Army.