Jolly was a sworn brother of the Black Company. He was mentioned in the Annals during their employment in the Lady's Empire. Before that, he was with the Company in Beryl, and made the trip across the Sea of Torments aboard Soulcatcher's giant galley, The Dark Wings, to Opal. He was considered by Croaker to be "professionally sarcastic" and "sour".

The Black CompanyEdit

Jolly was mentioned in the Annals in their first visit to Forsberg province. He was part of an advance team alongside Longhead and Doughbelly and were the first to arrive outside a village that had been razed by the Limper's army. Doughbelly rode back to the main force, and notified the Lieutenant that about 25 of the Limper's drunk men were still inside the village. The Lieutenant ordered the sergeant Elmo to investigate, who chose Otto, Silent, Peewee, Whitey, Billygoat, Raven, Croaker, and three others to accompany him. Doughbelly brought the group to Longhead and Jolly, and they entered the village, which was strewn with corpses of all ages. Jolly was present when Raven rescued Darling and Flick from the Limper's men by shooting two of them. The group departed after the Captain de-escalated the confrontation with the Limper's officer Lane.

When the Company was stationed at the fortress in Deal, Jolly accompanied Candy on one of the last weekly "turnip patrols" to the city of Oar to purchase supplies. He was accompanied by Raven, Doughbelly, and some others, including the civilian Flick. They all boarded in a stable owned by an old local named Cornie, who sold them out to the Imperial Colonel Zouad. Jolly and the other Company brothers fled the stable after a dozen local thugs hired by Zouad and his captain, Lane, set fire to the structure. Once outside, the attackers made it clear they only wanted Raven. When Flick threw himself in front of Raven to protect him, he was cut down and a melee ensued. Raven was severely wounded with almost thirty cuts, but the Company soldiers killed all the local thugs. Doughbelly and Jolly recognized Lane, and Candy observed Lane's superior (Zouad) hiding in the shadows during the fight. Candy and Doughbelly reported all this to Elmo and Croaker, which precipitated the Company's revenge against Zouad and his commander: the Limper.

Jolly and the rest of the Company later entered the city of Lords. There, Croaker mused how a little girl could become such a powerful evil as the Lady, and how a "giggling, inquisitive toddler could have become a Three Fingers, a Jolly, or a Silent".

Jolly was still with the main body of the Company inside Lords when it was besieged by Harden and other members of the Circle of Eighteen. He would have been very close to the thunderous sorcery duel between the Rebel leaders, and Soulcatcher and Nightcrawler. Jolly was with the Company when they all fled Lords and passed through the Windy Country with the help of Stormbringer's weather spells, keeping the Rebel at bay. Croaker was specifically very pleased to see Jolly at the Stair of Tear, as he had feared Jolly died at Lords.

Jolly's fate after these events was not recorded. However, as he was not among the 10 Black Company survivors of the Battle of the Barrowland many years later, he is presumed to be deceased by the end of The White Rose.

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