Captain is highest-ranking position of the Black Company. Two different men who held the position were also referred to as the Old Man by Company members. Military companies are usually between 100 - 300 soldiers, but the term "Captain" is used regardless of the size of the Black Company. The second-in-command position is Lieutenant.
The Captain is an elected position. Unlike membership in the Company, the captaincy can be resigned, though the resignation can be rejected.
During times when the Company's numbers are extremely small the Captain may also hold other offices. For example, Croaker was both Captain and Annalist during the Books of the South, when the reduced Company was attempting to return to its origins and during its early service to Taglios.
In the modern Annals, six different individuals held the position of Captain, with Croaker serving two different terms:
- The Captain
- The Lieutenant
- Croaker (first term)
- He was nominated at the Blue Willy immediately after the Battle of the Barrowland by Otto, after the Company was reduced to exactly 10 men: Croaker, Silent, Goblin, One-Eye, Otto, Hagop, Murgen, and the three Torque brothers: Stubby, Paddlefoot, and Brother Bear. He led the Company during its journey south and during most of its service to Taglios (the Shadowmaster wars) except during the Siege of Dejagore.
- Croaker (second term)
- He became captain again after Lady relinquished the position to him upon his return after being presumed dead. In his second term, he led the Company to final victory in the Shadowmaster wars (most notably in the Battle of Charandaprash and the Siege of Overlook). Then he became one of the Captured under the fortress with no name beneath the glittering plain. Despite being incapacitated for the next 15 years, he continued to hold the title of Captain, forcing the next ranking officer, Sleepy the Annalist, to be in charge.
- She officially became Captain only after Croaker, doubting his mental state after 15 years unconscious in the cave of the ancients, refused to resume the position. Before this, she had plenty of practice as de facto captain since she was the highest-ranking available officer (Annalist) throughout the 15-year gap between She Is the Darkness and Water Sleeps... the period referred to as the Captivity. During the first five years of this period she kept the Company alive despite losing the Kiaulune wars. Then, as official Captain, she dealt with the intrigues in Hsien (most notably, the File of Nine), and subsequently led the Company's assault on the Protectorate back in the homeworld. She won two major, hard-fought victories (the Battle of the Middle Ground and the devastating Battle at the Shadowlander cemetery), only to be killed during the Siege of Taglios.
- As Lieutenant, Suvrin was next in line for the Captaincy after Sleepy was killed in the Siege of Taglios. After finishing the fight there, he eventually led the remaining Company back to Hsien.