Admiral Theodore "Darkbleed" Lightborne, known simply as Darkbleed to most, is a member of the Bloodsail Buccaneers who is known for his outstanding naval service record to the Alliance of Lordaeron in the Second War and his unwavering loyalty to Duke Falrevere of Kul Tiras. Darkbleed and his fleet of three ships, The Blood Squall, The Sunwave Sunken, and The Reddened Seas stood out from the rest of the Bloodsail fleet because of Darkbleed's decision to never attack Alliance trade ships. On the contrary, Darkbleed himself received commendations from King Magni Bronzebeard and Highlord Bolvar Fordragon of the Alliance for saving several Alliance vessels from destruction at the hands of Horde privateering ships.
Admiral Darkbleed's fleet was recently lost upon the coasts of Stranglethorn Vale due to a violent storm, and with it a significant portion of Falrevere's treasure. Unwilling to give Darkbleed any more ships, Falrevere instead commissioned Darkbleed as the Bloodsail Ambassador to Stormwind in an attempt to repair some of his crumbling reputation with the Alliance. As Ambassador to Stormwind, Darkbleed has diplomatic immunity from those in the Alliance who perceive Duke Falrevere's decision to leave Admiral Proudmoore's fleet in the Third War as mutiny. Darkbleed has recently aligned himself with Lawbringer Mikaylus of the Crimson Horizon, whom he views as the salvation of the Alliance from the dark forces shadowing the world of Azeroth.
Theodore Lightborne is the only surviving son of Thaddeus Lightborne, a knight of Azeroth who fell defending Elwynn Forest from the orcish invasion during the First War. He fled Stormwind City prior to its razing at the hands of the Horde and went to live with relatives in Kul Tiras. He became a cabin boy aboard his uncle's schooner at the age of 12, where he was trained in dark magicks by a frequent passenger who spotted the boy's latent talent for manipulating dark energies. At age 18, when the Second War broke out, Theodore volunteered for service in Proudmoore's navy as mate aboard an oil tanker. After using magic to defend the unarmed vessel against a troll destroyer, Proudmoore recognized Theodore's talents by promoting him to captain of one of his battleships, The Blood Squall. During this period, he came to be known as "Darkbleed" by the enemy and his own crew because of his merciless, take-no-prisoners approach to naval combat and his ruthless and cruel treatment of any agitators or dissenters among his crew.
After the Second War, Darkbleed became friends with Duke Falrevere of Kul Tiras, a private naval commander closely allied with Proudmoore's navy. When Duke Falrevere made the decision to break away from Proudmoore's fleet during the Third War, Darkbleed surprised the crew of The Blood Squall by commanding them to break formation with the rest of the fleet and sail south with Duke Falrevere's ships. This act is viewed as mutiny by many, but it was a decision Darkbleed made because of his belief that the Plague of Undeath could not be stopped by military force and attempting to do so would only further service the enemy by turning his crew into zombie slaves. Impressed by Darkbleed's naval skill and leadership ability, Falrevere promoted Darkbleed to Admiral and gave him command of a subfleet of three ships. Darkbleed's subfleet managed to become one of Falrevere's most profitable, despite Darkbleed's refusal to attack any Alliance shipments. Darkbleed became the bane of goblin trade routes and one of the Steamwheedle Cartel's most wanted pirates.
Darkbleed is noted for his exceptional ability to broker diplomatic agreements with various factions. When he was stranded in northern Kalimdor for three months due to a mutiny aboard the Blood Squall, he became closely trusted by the Timbermaw Furbolg and Rivern Frostwind of the Wintersaber Trainers by assisting those factions in competing with other groups for survival. The Timbermaw entrusted Darkbleed with a sacred totem to call upon their ancestors to assist in battle, and Frostwind entrusted Darkbleed with Shy-Rutun, one of Shy-Rotam's daughters and princess of the Winterspring Frostsabers, as a personal mount.
In his time on land, since having lost his fleet on the coasts of Stranglethorn Vale, Darkbleed's primary diplomatic focus has been the kingdom of Stormwind. His proposal to the kingdom is to ally with the Bloodsail Buccaneers against the Steamwheedle Cartel, expanding Stormwind's territory into Stranglethorn Vale and giving the Alliance exclusive control of Booty Bay, an important trade route in the South Seas. Duke Falrevere sees this as a strong advantage for the Bloodsail Buccaneers to gain the upper hand over the Cartel-backed Blackwater Raiders, and would be willing to become an Alliance privateering organization in exchange for the Alliance's declaration of war upon the Cartel. This would create a reason for the goblins to re-align with the Horde and likely plunge the entire world into a theoretical Fourth War. In addition, the newer allies of the Alliance, the night elves and the draenei would be highly unlikely to stand by these actions and may even withdraw all support from the Alliance. This fits neatly into Duke Falrevere's agenda, as he does not trust these races and wishes to see human superiority and dominance in the world. While some of the more radical, Garithos-minded leaders in Stormwind support this idea enthusiastically, the general consensus is that the proposal is too radical to accept.
While the idea of starting the Fourth War is not enthusiastically accepted by Highlord Bolvar Fordragon or the leading nobles of Stormwind, the kingdom continues to maintain diplomatic ties to the Bloodsail Buccaneers through Darkbleed because they do possess one of the most powerful fleets in the South Seas and Stormwind would like to annex that fleet to their own. Stormwind has made the offer to Falrevere of a full pardon for himself and the entire organization in exchange for accepting a commission as Alliance privateers. Falrevere is unwilling to accept this offer, holding out on the hope that he can get the full support of Stormwind in his fight against the Steamwheedle Cartel.
Recently, Darkbleed has spent less time in the political arena and more in the military one, joining Lawbringer Mikaylus' Crimson Horizon.