James Phillip Hofdon was born to impoverished parents; his father, Phillip, was an unsuccessful blacksmith and his mother Penelope worked made additional coin by crafting blankets, curtains and rugs. Two years after James, his only other sibling, Thomas, was born. Both boys received no formal education and were apprenticed under their father, wanting to become smiths, but an abundance of men in the profession meant they were both more likely to become labourers.

This fate did not suit either James or Thomas. After James worked for two months on the construction of a sawmill in Brandywood, which now lays abandoned, he and Thomas enlisted as cheap protection for a merchant caravan, equipping themselves with crude weapons forged by their father. They hoped the caravan would eventually take them somewhere with better prospects. James was taught to fight by a much younger Johnathon Butcher, whom he would meet again many years later. While in the North Downs, on a trade route to Othrikar, James met Eliot Bencroft, a swashbuckling and ambitious character who planned to lead a small group of young refugees from the northern farms into Evendim. He bid farewell to his brother and joined Bencroft's party, one of the first groups to arrive in the Twilight Hills. 

On route to Evendim, the party's numbers swelled to over thirty men and women. Hofdon became friends in particular with two refugees from Stoneheight; Wal Simpkins, a stablehand, and Leighton Kipps, a barber. The party learned that the son of Stoneheight's mayor, Basil Gummidge, was rallying folk from the North Downs to settle in and around the ruins of Ost Forod. Bencroft begrudgingly agreed to visit the aspiring town, where several members of his party left the group and settled down permanently. The remaining party spent several weeks in Ost Forod, meanwhile Bencroft asserted himself as a councillor to Gummidge, but the men frequently disagreed with each other. During this time, a notorious outlaw named Percy Alroyd led a band of fifty brigands and sellswords into the north from Bree-Land and claimed the north eastern coast of the great lake, establishing his base on the island Rantost. Alroyd's gang were the first real tomb robbers; they traveled around the territory, pillaging Arnorian tombs and loading relics on to barges and wagons to be transported back to Bree and the Shire for sale. Conflicts between Bencroft and Gummidge continued until Bencroft and his followers left Ost Forod and requested to join Alroyd's gang. Alroyd accepted the offer, and not long passed before Bencroft was named his lieutenant.

Hofdon's practical, no-nonsense nature and his martial ability had been recognised by Bencroft, who convinced Alroyd to appoint Hofdon as a captain of the gang. As Simpkins and Kipps were closer to Hofdon than Bencroft, they chose to follow him instead of Bencroft. Hofdon commanded a total of eleven men, excluding himself, and worked to a quota set by Alroyd to salvage a certain value of relics each week. Hofdon's party was largely successful, bringing in an admirable amount of coin from their findings.

The Rantost gang was only the first of three tomb robber gangs to settle in Evendim. A relatively small band of brigands led by Bart Madgett settled in Barad Tharsir, on the shores of the Brandywine. In addition to plundering tombs and ruins, the Barad Tharsir gang commonly harried barges delivering supplies to the Rangers of the North and settlers in Ost Forod. A third gang of Blackwold deserters arrived in Evendim later still, but with a larger force and equipment funded by Angmarim. They settled on the road of tombs, fortifying the overlooks of Men Erain and fighting with the Wardens of Annuminas. Hostility fell between all three gangs, and only the area immediately around Ost Forod was considered a neutral zone, as Gummidge's enforcers and mercenaries guarded the town. 

One year ago The Bloody Dawn was hired by Gummidge, at the behest of his lieutenant, Tom, to put down a plot by the Rantost gang to assault and capture Ost Forod. A member of the Dawn was a past associate of Bencroft, and although he struggled to stay in contact, eventually they organised for Bencroft to support the Dawn once they landed on the island, on the condition that the gang would not be so terribly harmed and he could succeed as the master. After instigating violence between the gangs in order to reduce Alroyd's numbers on Rantost and distract his men in the field, the Dawn was sent to Rantost to eliminate Alroyd and the gang's threat. Two Dawners went to meet Bencroft at the southern tip of the island once the plan was launched, only to find themselves surrounded. Hofdon knew nothing of Alroyd's plot, but had learned of Bencroft's involvement with the Dawn, and brought it to Alroyd's attention, though he pleaded for Bencroft to be exiled instead of exectued. Alroyd agreed, and Bencroft was subsequently banished from Rantost prior the Dawn's arrival, allowing the tomb robbers to capture and imprison every Dawn mercenary on the island.

While in exile, Bencroft unsuspectingly rallied many of the men who had been dispatched to outposts to defend from the other two gangs, including Simpkins and Kipps, and arrived at the beach across the water from Rantost at the time when the Dawn was escaping. Bencroft's men relieved the Dawn mercenaries and together they overwhelmed Alroyd's remaining force, only for Alroyd to survive with Hofdon carrying him away from the battlefield.

The Dawn discovered that Gummidge himself had instigated the plot, intending to sell Ost Forod to the gang and flee to Bree. Bencroft took control of the remaining gang and Rantost, then pledged support to the Dawn, promising that his men would flank Gummidge's men when they attempt to take Ost Forod. The Dawn, with Simpkins and Kipps, passed through secret tunnels into Ost Forod during Gummidge's assault. The Dawn reached Gummidge and dispatched him while Bencroft's men fought off Gummidge's supporters. Two days later, Bencroft and Gummidge's elderly lieutenant, Tom, took control of Ost Forod. They ruled jointly until Tom's retirement to Bree-Land. To this day, Bencroft governs the town, hoping to see it prosper, though his rule is dictatorial by nature and public punishments are commonplace.

Alroyd hated Hofdon for convincing him to let Bencroft live, though he was in health too poor to act against him. A man calling himself Garvey Widdup arrived to assassinate Alroyd, and Hofdon did not stand in his way. Widdup explained the week's events to Hofdon, and that Alroyd had never in fact been involved in any sale of Ost Forod; he was merely used as a decoy. After having betrayed Bencroft, Hofdon reasoned it was inappropriate to reason with the new most powerful man in Evendim and returned to Bree.