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Captain is the leadership 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 when the Company traveled south and during its early service to Taglios.

In the Black Company series six different characters have held the position of captain of the Black Company, with Croaker serving two different terms.

  1. The Captain
  2. The Lieutenant
    • This man's actual name is never recorded in the annals. Although elected captain, he continued to be called the Lieutenant. Led the Company during its service to Darling and the White Rose Rebellion.
  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)
  6. Sleepy
  7. Suvrin
    • Led the remaining Company back to Hsien.