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 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 Plain of Glittering Stone. 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 being liberated from the Captivity, refused to resume the position. As Annalist for 15 years with no one ranking above her (the period referred to as the Captivity) she had plenty of practice as de facto captain during the Kiaulune wars. As official Captain, she dealt with the intrigues in Hsien (most notably, the File of Nine), and then led the Company's assault on the Protectorate. She was 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.