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Shadow was a former sailor from the Juniperen ship called Cranky Bitch who joined the Black Company by the time of "Wet Dream Fish Story", a short story of the On The Long Run arc. He got his nickname because he was so thin that he "didn't cast a shadow", and was known to Croaker the physician because he was the “hard-luck” victim of a wide variety of accidental injuries and wildlife bites during their time in the western wilderness.

Before "Wet Dream Fish Story"[]

Shadow is not mentioned by name in the novel Shadows Linger or the subsequent short stories "Cranky Bitch" or "Leta of the Thousand Sorrows", but it is known he was present for those events. In Shadows Linger, Shadow was part of the Juniperen crew answering to Master Sylus that had been hired by Raven to sail his large, new oaken ship called Cranky Bitch. Shadow, Master Sylus, and the rest of the crew from Juniper were all "orphaned" following the catastrophe that befell their home city: the Battle of Juniper and the Lady’s suppression of Hargadon's revolt in the aftermath. However, they did not witness these events, as they had already departed Juniper toward Chimney with Raven and his young ward Darling.

Shadow was aboard the Bitch during the three small sea battles fought against the pirates from the Pocatose archipelago in the waters of the Gap in "Cranky Bitch". Croaker would mention later that he fell from the rigging on two separate occasions. Next, he was among the unspecified number of sailors who chose to join the Black Company, and disembarked from the vessel a final time. After a difficult trek through rough terrain, it is likely Shadow was one of the many men who were bedded by the supernatural woman known as Leta in "Leta of the Thousand Sorrows".

Croaker also mentioned that Shadow was bitten by a poisonous snake, and separately, a poisonous spider. The latter bite made the flesh in his calf rot, causing Croaker to remove half a pound of muscle to save him.

"Wet Dream Fish Story"[]

In "Wet Dream Fish Story", Shadow was a subordinate of Candy (the Company’s the second-in-command). After he was tasked with felling trees to gather lumber for the bridge repairs the group was undertaking, he was struck in the belly when a tree trunk bounced. His companions removed the splinters, stopped the bleeding, and took him to Croaker. When the physician confirmed that the injury was not serious, Candy jokingly told Shadow to return to work, but for a moment Croaker thought Candy was serious.

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