Longshadow was a sorcerer who dwelt in the extreme southern reaches of the world. He was a member of the Shadowmasters and the main antagonist of the Books of the South. He played a major role in both bringing the Shadows into the world, and also in keeping them contained to the Plain of Glittering Stone.
Although much of Longshadow's background is unknown, the Black Company did discover that he was originally from the Land of Unknown Shadows, where he was a wanted criminal. At some point prior to the events of the White Rose, he ventured out onto the Plain of Glittering Stone and learned to gain a measure of control over the Shadows. In the "home" world, he joined together with the Shadowmasters, who were planning to use controlled shadows to conquer the world. However, when the less-experienced Shadowmasters tinkered with the gateway onto the Plain of Glittering Stone, damaging it to the point where the Shadows could escape freely. To save the world from being overrun and destroyed, Longshadow repaired the gate, tying his own true name to it. In doing so, he ensured that if he died it would cause the Gate to break open.
Against the Black Company Edit
Upon the arrival of the Black Company in Taglios, the war quickly turns against the Shadowmasters. Longshadow spends the war hidden away in his fortress, Overlook, mostly trapped inside his own fears through the manipulation of the goddess Kina. His only real contribution to the early war effort is dispatching Shadows and specially bred spies who can control them to monitor the actions of the Company. He also coveted the knowledge that Lady possessed, and attempted repeatedly and unsuccessfully to kidnap her.
Longshadow acquired several allies to replace the defeated Shadowmasters in the form of the traitor, Mogaba, the Living Saint of the Stranglers, Narayan Singh, and Howler, one of the Ten Who Were Taken who the Company discover survived the Battle of Charm. The Howler would eventually head up Longshadow's final attempt to capture Lady, but managed to grab Soulcatcher instead. Although Longshadow hoped to gain information, or even cooperation, from Soulcatcher, she easily escaped from Overlook and worked at odds with the Shadowmaster afterward.
As the Company pushed south, Longshadow seemed to regain some measure of his confidence (which had previously been badly sapped by Kina's meddling) and sent larger and more powerful groups of shadows to attack the Company. Due to the fireball launcher artillery developed by Lady, however, the Shadows proved largely ineffective as a fighting force, and failed to halt the advance of the Company.
In the end, Longshadow was captured by the Black Company at Overlook, and subsequently became one of the hostages beneath the Plain of Glittering Stone. Once the imprisoned there were freed and the Company journeyed to the Land of Unknown Shadows, they used Longshadow as a bargaining chip to gain the cooperation of the authorities there, buying the time they needed to recover and re-arm for battle against Soulcatcher.