Ouroboros is the main villainous organization of the Kiseki/Legend of Heroes 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 Apostles (or Anguis). Underneath that rank are called the Legion/Enforcers.

Ouroboros is also mainly composed of soldiers and machines.

the Ouroboros organization and it's members have been know 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: 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.
  • The Third Anguis: (The Faceless):
    • George Weissman. Formerly a bishop of the Septian Church and the third Anguis of Ouroborus. Intelligent yet cruel in nature, 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 in order to use it for herself. She replaces Weissman's position at the end of Ao no Kiseki.
  • The Fourth Anguis: Only appears during a conversation in The 3rd.  Speculated to be Lechter Arundel.
  • The Fifth Anguis: unknown. A possible theory is that it may be Barkhorn.
  • The Sixth Anguis: F Novartis (The Professor) Head scientist that manufacture 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: (The Steel Maiden ) Arianrhod. Commander of the Stahlritter and strongest warrior in all the nation of Zemuria. Also an Awakener.
  • members of the Legion (Enforcers)

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 a Legion 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 Timeless Blaze): 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. Mostly uses Mirage orbment. Deceased
    • Enforcer No III: unknown
    • Enforcer No IV: unknown
    • Enforcer No V: : unknown
    • Enforcer No VI: Lucciola (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 (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 Kruger (The Severing Chains) She is revealed to be a member of Ouroboros in Sen no Kiseki, declaring herself as a "Legion in hiatus". She has also been the Reinford's family maid for many years. Her goals and true allegiances are unknown in Trails of Cold Steel 2 she is fighting against the people she works for, hinting that she might have redeemed herself.
    • Enforcer No X: Bleublanc (The Phantom Thief) A masked man with a white cape often seen with a rose. He was a famous thief from Zemuria under the alias "Phantom Thief B". He is obsessed with beauty He cooperated with Weissman's plan as 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 Hayworth (The Angel of Slaughter): A young girl with purple hair and former member of Ouroborous.
    • Enforcer No XVI: Shirley Orlando (Bloody Shirley): The battalion commander of the Jaeger group Red Constellation and daughter of its sub-leader Sigmund. After the events of Ao no Kiseki, she and Mariabell were invited to join Ouroborous, the later becoming an Anguis. Cousin of Randy Orlando and somewhat of a rival to Fie.