Spiff was a sworn brother of the Black Company who ranked at least sergeant by the events of She Is the Darkness. He would serve under Sleepy throughout the period called the Captivity (most importantly the Kiaulune wars) as well as during Water Sleeps and Soldiers Live. He was almost certainly from Taglios.
She Is the DarknessEdit
Spiff – along with Red Rudy, Big Bucket, Shiner, and Kloo – was one of the sergeants and officers Croaker bellowed for after he was informed by Isi and Ochiba that their important captive, the wizard Smoke, had been assassinated.
Spiff was not among the Captured and served Sleepy and Ky Sahra in the Company's grim Kiaulune wars against Soulcatcher. Before or during these events, Spiff became acquainted with Khusavir Pete, another Company sergeant, one who disappeared when the Bahrata Battalion was ambushed and wiped out at Kushkhoshi. Spiff did not know that Khusavir Pete was a defector who orchestrated the incident with Soulcatcher and survived. After that incident, the Kiaulune wars were won by Soulcatcher, so Spiff then went underground in Taglios with the surviving Company.
Sleepy, the Annalist during Water Sleeps, considered Spiff to be among "the men I had known the longest and trusted the most", along with Runmust Singh and Riverwalker. This would be on account of his loyalty to her during the Kiaulune wars.
Spiff and the "barely competent" Pooch were ordered by One-Eye to assassinate Adoo, the gateman of the library of Taglios. This was simply one part of the Sleepy's rush of activity to conceal the Company's whereabouts.
Like many Company brothers and allies, Spiff learned how to play tonk. He was playing the card game with Sleepy, Kendo Cutter, and JoJo when Sleepy made the decision they should kidnap Aridatha Singh and introduce him to their captive, Narayan Singh.
He participated when the Company subdued a group of about 50 Protectorate-aligned Shadowlanders who had trudged out of "the New Town" (Kiaulune) to confront them. The event occurred without bloodshed, and Sleepy recalled that it was probably Spiff or Wart who remembered to make their new captives temporarily lie down on their bellies after they turned over their weapons. The highest-ranking captive, Suvrin, would go on to become the Company's leader in subsequent years; the others were set free. Other Company members and allies who were present with Sleepy, Wart, and Spiff during this event were Goblin, Tobo, Ky Sahra, and Uncle Doj.
Spiff next accompanied Sleepy, Tobo, Goblin, Vigan, and others during the Company's encirclement of the Protectorate fort that guarded the shadowgate. The fort contained a garrison of about a dozen men commanded by Khusavir Pete, a former member of the Company whose defection and betrayal helped Soulcatcher win the Kiaulune wars and consolidate her Protectorate. The Company used fireball projectors and sorcery to burn them out. Spiff was the first to recognize Khusavir Pete. But, like everyone else except Sleepy, he did not know the story of Pete's betrayal and was initially happy to see him. Sleepy now publicly exposed Pete's treachery.
Spiff would join the rest of the Company as they passed through the shadowgate, crossed the glittering plain, retrieved the first set of 5 Captured from the cave of the ancients, and finally entered the strange new world of Hsien.
Spiff was part of Croaker's eclectic group of Company men and allies permitted by Sleepy, the Captain, to enter the Voroshk world to get revenge upon the forvalaka Lisa Daele Bowalk. Others who were present during this operation were Lady, Murgen, Thai Dei, Willow Swan, Uncle Doj, Cletus, Loftus, JoJo, and a group of Unknown Shadows called the Black Hounds. Spiff and JoJo were both killed by shadows during the Company's first night there. These shadows had breached the world's shadowgate after Bowalk forcibly entered years beforehand, but they were no longer "feral", as they were subsequently tamed by the Voroshk. After Spiff and JoJo died, the remaining group was joined by Goblin (possessed by the Khadidas) and the Chu Ming brothers, and they succeeded in assassinating Bowalk.