After the deaths of the Thistledown farming family at the hands of the barghest whelp Ulgulu (who was disguised as a drow during the act), a bounty of 2000 gold pieces was placed on the head of Drizzt Do'Urden. Roddy McGristle left Maldobar to find Drizzt, eventually finding and attacking him with Bleeder and his two dogs. During the fight the agile drow killed one of the dogs in self-defense and McGristle lost an ear. He would then be led not so much by the promise of gold, but for his wounded pride and hatred. He joined the party pursuing Drizzt, and despite reaching the same conclusion on the drow's innocence, he kept pushing for his capture and execution out of spite.
“My head would not bring you your bounty,” Drizzt retorted.
“To Nine Hells with the gold!” Roddy yelled. “Ye took my dog, drow, an’ my ear!” He banged a dirty finger against the side of his scarred face.”
McGristle eventually tracked Drizzt to Mooshie's Grove, the haven of the famous ranger Montolio Debrouchee. There, he allied himself with the local orcs (led by their king, Graul) in the hopes of revenging himself on the drow. Montolio and Drizzt repelled their subsequent assault on Mooshie's Grove, and McGristle was captured by the elf Kellindil, an associate of the ranger Dove Falconhand. The quickling Tephanis, searching for a new master (the previous three having been killed by Drizzt or his associates), cut McGristle's bonds, allowing the bounty hunter to overpower and murder his elven captor. Tephanis, more interested in companionship than revenge, convinced McGristle that Drizzt had been killed in the unsuccessful assault on Mooshie's Grove. The bounty hunter, believing himself to have been cheated out of his revenge, spent the subsequent six years growing ever more embittered and volatile, until a chance tavern encounter alerted him to Drizzt's survival.
After tracking the drow to Mirabar, McGristle's plans for a confrontation were once again foiled by Tephanis, who lured Drizzt and his travelling companions, the Weeping Friars, into the lair of the red dragon Hephaestus. Drizzt managed to escape once more, and McGristle murdered Tephanis for his treachery before picking up the trail once more. He tortured the Weeping Friars for Drizzt's whereabouts, and learned that the drow was headed for the settlement of Ten Towns in Icewind Dale.
Upon arriving in Ten Towns, McGristle learned that Drizzt had taken up residence in the wilderness near Kelvin's Cairn, also home of the dwarf Bruenor Battlehammer and his clan. Thinking the deposed dwarf king would be sympathetic to his cause, McGristle was disappointed to discover that Bruenor showed no interest in aiding him in his search. He was able to discern, however, that Bruenor's adopted human daughter Cattie-brie knew more about the drow than she was letting on. After being expelled from the dwarf's hall, McGristle followed the young girl to Drizzt's camp on the mountain and lay in wait. He violently accosted her when she set out to return home, drawing the dark elf out of hiding. McGristle was bested in combat once more by Drizzt, and the defeated bounty hunter attempted to goad his nemesis into killing him. Drizzt refused him this satisfaction, knocking McGristle unconscious instead.
Upon waking, McGristle once more set out after the drow, emboldened by the knowledge that Drizzt's "weakness" would never allow him to kill his relentless pursuer. He was met by Bruenor Battlehammer, who had by then learned the entire tale of Drizzt and, more damning, the bounty hunter's rough treatment of Cattie-brie. The subsequent exchange left McGristle convinced that Bruenor did not share the dark elf's predilection for mercy, and the bounty hunter was soon seen departing Icewind Dale with his dog (now one leg short), never to return.