Ouroboros is the main villainous organization of the Legend of Heroes: Trails series mostly manipulating events from behind the scenes they have members that each have their own goals and plans. Most of the members of Ouroboros are unknown as most of their work is done through subterfuge and deceit.
The main members of Ouroboros are called the 7 Anguis. Underneath that rank are called the Enforcers.
Ouroboros is also mainly composed of soldiers and machines.
Ouroboros and it's members have been knowing to comment robberies, working with terrorist, trying to start wars and even helping others start wars, murder, selling stuff on the black market, as well as making robots and putting them in places where both people and the wildlife could get hurt it is unknown what their leader's main goal is.
The leader of Ouroboros is known as The Grandmaster but the only thing that is known about her is that she is a female.
Members of The Anguis (The Apostles)
- The First Anguis: The unknown might be the leader of the Anguises.
- The Second Anguis: (The Azure Abyss) Vita Clotilde. Former Descendant of the Hexen Clan and sister figure to Emma Millstein. The Leader of the Phantasmal Blaze Plan. While she temporarily left the society after they planned to help out the Gnomes and the Ironblood's to continue the plan, she eventually retuned to the society after the events of Trails into Reverie.
- The Third Anguis: (The Faceless) (The Wellspring Alchemist):
- George Weissman. Formerly a bishop of the Septian Church and the third Anguis of Ouroborus. Intelligent yet cruel, he can control the memories of a person. Deceased
- Mariabell Crois. Daughter of Deiter Cross and childhood friend of Elie MacDowell. Secretly worked with her father to recreate the Demiourgos but betrays him to use it for herself. She replaces Weissman's position at the end of Trails to Azure.
- The Fourth Anguis: Ellroy Harwood (The Thousand Oathbreaker) An assassin originally from the Order of the Moonlight Horse assassin group before it was destroyed by Ouroboros. Later joined the group with fellow survivors Lucretzia Isselee and Sharon Kreuger. First appears during a conversation in The 3rd and as a silhouette in Trails of Cold Steel 3 before being properly introduced in Kuro.
- The Fifth Anguis: Unknown. His voice in the Vita release of The 3rd implies that he is an old man.
- The Sixth Anguis: F Novartis, (The Professor) Head scientist that manufactures Ouroboros' robots. One of his creations was Pater-Mater. A typical mad scientist figure and leader of the Azure-Zero Project (The first phase of the Phantasmal Blaze Plan)
- The Seventh Anguis: Arianrhod, (The Steel Maiden), Lianne Sandlot. Commander of the Stahlritter and strongest warrior in all the nation of Zemuria. Originally known in life as Lianne Sandlot who fought in the War of the Lions alongside Emperor Dreichels. Also an Awakener and met her end at the end of the third rivalry. Deceased.
Enforcers of Ouroboros
Enforcer No 0: Campanella (The Fool) A young man with a tattoo under his right eye. Although he looks like a normal young man, according to Joshua, even after his days as an Enforcer Candidate (about 7 years ago) Campanella doesn't seem to change at all raising debate whether he is a human or not. He possesses high magic capabilities.
- Enforcer No I: McBurn (The Almighty Conflagration): A tall man with the ability to control flames. Is one of the more powerful members along with Arianrhod and Loewe, the former admitting that he may be able to best her in combat. He also possesses a divine weapon like them. Initially bored and apathetic due to a lack of challenge, his fight with Rean and Victor S. Arseid reignited him (figuratively and literally).
- Enforcer No II: Leonhardt (The Bladelord) A young man with silver hair and wielder of the Divergent weapon Kernviter as well as a brother figure to Joshua. Before joining joined Ouroborous, he lived a peaceful life in the village of Hamel with Joshua and his older sister Karin. Unfortunately, years would pass and the village would be razed by mercenaries and soldiers alike in what became known as The Great Tragedy. Although Joshua and Loewe came out alive, Karin would sacrifice herself to save them. As a result, Loewe's personality changed completely and held the belief that humanity must be tested. It mostly uses Mirage ornament. Deceased
- Enforcer No III: Lucretzia Isselee (The Golden Butterfly) A young woman with a butterfly motif in her clothes who was originally an assassin in the Order of the Moonlight Horse along with Ellroy Harwood and Sharon Kreuger who joined the society after Ouroboros destroyed it.
- Enforcer No IV: unknown
- Enforcer No V:: unknown
- Enforcer No VI: Luciola (The Bewitching Bell) A woman that uses fans as her weapons. She excels in using a combination of fire and wind Orbment, she also has the power to summons mythical creatures but what makes her a formidable enemy was her skill to creates illusions with her bell.
- Enforcer No VII: Nothing about this character is currently known.
- Enforcer No VIII: Walter Kron (The Direwolf) A former martial artist of Calvary's renowned Taito Style, just like Zin. He was once good friends with him and Kilkia, but his obsession with the "Murderous Fist" style would lead him to kill Kilkia's father.
- Enforcer No IX: Sharon Kreuger (The Severing Chains) (The Severing Eclipse) She is revealed to be a member of Ouroboros in Trails of Cold Steel, declaring herself as a "Enforcer on hiatus". Originally a girl codenamed Krueger, she was originally part of The Order of the Moonlight Horse who were a group of assassins that were wiped out by Ouroboros with Ellroy, Lucretzia and Kreuger joining the society afterwards. She has also been the Reinford's family maid for many years as a way of atonement after believing she accidentally killed Franz Reinford and would only return to the society of he ever came back.While she fought against her former society members in Trails of Cold Steel 2, she eventually returned to Ouroboros in the final chapter of Trails of Cold Steel 3 after learning that Franz had come back as the chief of the Gnomes Black Alberich. After staying with the society for most of Trails off Cold Steel IV however, she realizes that Alberich isn't actually Franz himself and decides to leave the society for good following this.
- Enforcer No X: Bleublanc (The Phantom Thief) A masked man with a white cape often seen with a rose. Originally starting as a petty thief in Erebonia and later becoming a con artist that constantly ccommitted identity fraud, he was later caught and eventually broke out of prison under his new identity. He later becam a famous thief from Zemuria under the alias "Phantom Thief B". He is obsessed with beauty He cooperated with Weissman's plan to steal "Hope" because he thinks that the faces of those that resist and cling on to hope is beautiful. He is a recurring antagonist in the series and rival to Olivert Reise Arnor.
- Enforcer No XI: unknown
- Enforcer No XII: unknown
- Enforcer No XIII: Joshua Bright (The Black Fang): An expert in stealth and assassination. Redeemed before the events of the first game of the series and is trying to atone for his sins as a bracer.
- Enforcer No XIV: unknown
- Enforcer No XV: Renne Haywood (The Angel of Slaughter): A young girl with purple hair and a former member of Ouroborous.
- Enforcer No XVII: Shirley Orlando (Bloody Shirley) (The Sanguine Ogre): The battalion commander of the Jaeger group Red Constellation and daughter of its sub-leader Sigmund. After the events of Trails to Azure, she and Mariabell were invited to join Ouroborous, with her becoming an Enforcer. Cousin of Randy Orlando and somewhat of a rival to Fie.
- Enforcer No XVIII: unknown
- Enforcer No XIX: Cedric Reise Arnor Crown Prince: The former Crown Prince of the Erebonian Empire and a former member of the Ironblood's led by Gilliath Osborne. During the October War, Cedric was captured and used by Duke Cayenne to pilot the Testa-Rossa Divine Knight in Trails of Cold Steel 2 and awakened it as the Vermillion Apocalypse. After being saved by Class VII however, Cedric became cursed and started to slowly turn evil until the curse on him was finally broken near the end of Trails of Cold Steel IV by his friend Kurt Vander. Despite coming to his senses however, he later asked Shirley if he could join Ouroboros at the end of the game with him officially becoming Enforcer No XIX by the time of Trails into Reverie.