In the years leading up to Shadows Linger, the Black Company crossed the Plain of Fear alongside larger armies of Imperial regulars, under the aegis of the Taken Whisper and Feather. They followed a dedicated caravan route "the Plain's denizens generally" respected. Despite their powerful backup, the Company still lost two men – Cougar and Fleet – to unspecified dangers of the Plain when the pair left the route to explore. The rest of the Company was helpless to save them despite their horrified screams. In the eastern town of Tome, Croaker would recall this memory with immense dread and would soon learn they had been ordered to return west, back across the Plain.
Croaker mentioned Fleet and Cougar in his lost Annals of Port of Shadows as well, but did not name them there, instead simply referring to them as "two idiots".