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.

  1. The Captain
  2. The Lieutenant
    • This man's actual name is never recorded in the available Annals. Although elected captain, he continued to be referred to as the Lieutenant. He led the Company during its service to Darling and their flight eastward.
  3. 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 three newer members. He led the Company during its journey south and in its early service to Taglios.
  4. Lady
    • Unofficially assumed captaincy and rebuilt the military strength of the Company after Croaker's presumed death and the isolation of other officers during the Siege of Dejagore. She relinquished the position to Croaker after his return.
  5. 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 again led the Company until 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, although the de facto captain was Sleepy, the Annalist.
  6. Sleepy
    • 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 Battle of Taglios.
  7. Suvrin
    • As Lieutenant, Suvrin was next in line for the Captain role after Sleepy was killed in the Battle of Taglios. After finishing the fight there, he eventually led the remaining Company back to Hsien.