Jamie manages the “back of house” operations at the Winter’s Reprieve Inn, which leaves gambling, whoring, loaning, and fencing under his charge. Meanwhile his brother James oversees the more reputable “front of house” business, i.e., the inn and tavern. One victim of Jamie’s predatory business practices is Ser Perin Pryor, who owes a considerable (50 gold dragon) gambling debt.

Ser Darron, Ser Carson, Jardon, and Thomas met Jamie in 283 AC. The Jasper men sought to have Perin’s debts forgiven. After some negotiating Jamie agreed to waive the debt if his competition (a dingy wharf-side gambling den called The Falcon’s Nest, operated by a man named Merle) were put out of business. They failed.

One month later Perin returned to Jamie’s game to gamble, seemingly unaware that he had an outstanding debt. After allowing a small line of credit to the knight young Lord Theodore Jasper joined the game; it was during this time that Jamie signaled James who left the inn to fetch the city watch. The men of House Grafton arrested Perin as a debtor. The next day, under questioning by Calaila and Dolins, Jamie revealed that Terry is a guest of the inn and that Rusty is likely after her because of what she took. Calaila paid a silver for the information.

In April of 284 AC, during a visit to Gulltown, Darron, Jardon, and Maester Thaddeus returned to Winter’s Reprieve. There, Jamie had a boy of 12 minding the bar and business was booming despite the early hour. Jamie attempted to berate the Jasparians into admitting they had double crossed him and had attempted to set fire to the “WR” instead of the Falcon’s Nest as agreed. None would admit culpability, but in a flippant gesture Darron offered to set fire to the now abandoned Falcon’s Nest as recompense; to the surprise of all Jamie agreed. Jamie had also revealed that just after the debt-foregiveness-fiasco that James and Merle had killed each other in a street fight.

Jamie was surprised to see the three hapless Jasparians re-enter Winter’s Reprieve later that night. They explained that they had purchased the Falcon’s Nest when Lord Grafton had interrupted their arson attempt. Although initially miffed that they had become his competition ultimately a deal was struck between the parties. Both agreed to be good neighbors, Ser Darron paid 10gd to Jamie, and Jamie expressed that he would be willing to act as a fence and an agent supplying them with jobs from a man in Old Town.

When Teddy, Dolins, and Calaila returned to Winter’s Reprieve (accompanied by Ser Denys) they sought out Jamie, asking about a unique dagger. Jamie feigned memory problems and suggested gold may help. A brief negotiation ensued in the kitchen in which Jamie shared that he had seen a carpenter named Devin with the dagger and the Jasparians agreed to return with gold for him if the information he gave them was fruitful.

It wasn’t until April of 285 AC that House Jasper returned to Winter’s Reprieve. Teddy and Calaila spoke with Jamie; the former paid 1gd for the information Jamie had given months earlier. Another 3gd were paid for information about Terry’s whereabouts; Jamie suggested Lannisport or Oldtown. Several hours later, as the Jasparians were leaving Teddy realized that someone had lifted his coin purse; when this was brought to Jamie’s attention he beckoned to a man (Madsen) and left the room to discuss the matter. The pair returned to sooth rustled feathers as a brawl was about to erupt.