The first time Conan encountered them was in Khoraja, where Sergius of Khrosha - then leader of the Brotherhood - was fencing goods and recruiting. They had a brief (but bloody) argument in the tavern when Sergius interrupted the barbarian's meal. The next time they met was when Conan led his Free Companions to ravage the south-western shores of the Vilayet Sea. Sergius and his cronies paid him a visit warning him that increased pillaging would attract the attention of King Yildiz (ruler of Turan) and that he should limit his activity to the southern shore and split the plunder with the Brotherhood. Conan had none of that and they parted as enemies. After that they captured Afreet one of the mercenary captains and delivered him to Shah Amurath along with information about the location of Conan's camp. That allowed the Turanians to surprise and massacre the Free Companions.

Some time later they landed on the Isle of Iron Statues where they again met Conan who challenged Sergius to a duel. According to the Brotherhood's rules, the one 'who kills a leader becomes a leader' and after killing Sergius the Cimmerian became the new leader. For some time they were robbing trading ships on the Vilayet Sea, until one day they were ambushed and their ship the "Olivia" sunk with most of the crew.