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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:

  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)
  4. Lady
    • Unofficially assumed the 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. This claim was contested by Mogaba. She relinquished the position to Croaker after his return.
  5. Croaker (second term)
  6. Sleepy
  7. Suvrin
    • 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.