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Status: Alive
Age: 29
Race: Human
Gender: Male
Class: Black Mage
Nation: Remon
Era: Third Age
"Simon says: listen to his every word carefully, or suffer the consequences."

Simon is a member of the Totenkopfs. He has been responsible for kidnapping Hannibal Losstarot, persuading Arbriel Conrad to join the Totenkopfs' ranks and developing the Plague of Undeath. He has also helped found the Crimson Coalition in Trinity Gask in 1017 AE and has become the Totenkopfs' representative in the Coalition Council. He is an intelligent man with great ambition, and he won't hesitate to crush anyone who stands in his way.


Early Years[]

Simon was a young man from Ravensworth who saw the destruction which the Yamatian Invasion and the Great War caused firsthand. He lost his pregnant girlfriend to the blades of the Yamatians in a battle over the control of Ravensworth, and this drove him off the edge. By the time the Grand Alliance moved its focus on liberating Maar Sul, Simon's psyche was already cracking, and he was about to commit suicide.

It was then that he met with the enigmatic Master who managed to convince him to not kill himself. The Master was a smooth talker and provided Simon with a new, dark view of the world which made perfect sense in the wartorn world. Convinced of the righteousness and necessity of the Master's plans for the future of the world, Simon joined the cult dedicated to the Master's ideals, known as the Totenkopfs.

Simon followed the Master during the final years of the Great War and learned the art of manipulation from him. He turned out to be a prodigy in this regard, and the Master gave him increasingly more difficult missions which he turned to the Totenkopfs' advantage. By the time the Cataclysm struck the world, he became one of the top Totenkopfs, the Blessed, thanks to his intellect and ruthlessness.

Godslayer Era[]

The Age of Emptiness[]

"If you join us, we can provide you with many things. Wealth? We have more money than we can spend. Disciples? We number in the thousands. A base? Pick any city in any country, and you'll find us there. Power? A man of your status will be given a worthy position, and you'll have the world in your palm."
—Simon to Arbriel Conrad

The Master found out about the arrival of Belial de Ardyn to Ravensworth in 1016 AE and ordered a group of Totenkopfs, under the supervision of another Blessed named Cain Highwind, to stay on the lookout because Belial would play a crucial role in the Totenkopfs' plans. When one of the Totenkopfs, Zenobia, began causing trouble at the docks of Ravensworth, Cain sent Simon to stop Zenobia from killing Belial. Zenobia was less than pleased by the interruption but a mild threat from Simon made her follow him quietly to their hideout.

Simon and Cain used the chaos that Zenobia's meddling had caused to release the Omari fish, which had been infected with a variant of the Blood Fever, to attack the survivors of Belial's crew. The Wanderers came to the crew's aid and defeated the fish, but Simon managed to collect valuable data on the mutated beast's behaviour and increased strength. Simon's data would later prove to be crucial for the mutation of the Blood Fever which would become known as the Plague of Undeath.

Simon's next assignment was to intercept with Arbriel Conrad, a cleric whom the Master hoped to use to further his plans. The meeting between Arbriel and Simon went well thanks to Arbriel's curiosity and ambition and Simon's oratory skills, and Arbriel followed him to Ravensworth to meet with Cain.

A Game of Deception[]

"But why would your benefactors help us?"
"Let's just say that it serves our interests to see you win this war."
Boris Ivanov and Simon

The surprising emergence of the Proninist Party nearly ruined the delicate plan of the Totenkopfs, but the Master saw the Proninists as a new, powerful means to an end which he could use against the growing force of the new Grand Alliance. While Cain took care of Arbriel and Zenobia and Jacob Seneron caused a ruckus in Remonton, Simon was sent to Maar Sul where the Proninists had been gaining a foothold.

Simon met two Proninist leaders, General Boris Ivanov and Colonel Mikhail Gorbachev, during one of their strategy meetings. Although the two commanders were less than friendly, Simon managed to convince them to hear him out. He appealed to them by promising them unlimited power which they would need once Maar Sul and Marcus Sarillius's Grand Alliance joined forces.

Although the two commanders were skeptic, they understood that their current resources and manpower would not last indefinitely against the Alliance, so they decided to send Simon to Trinity Gask with Captain Ivan Chernenko to form an alliance with the Rebels and the Totenkopfs.

Echoes of War[]

"You've served us well, and you deserve to be rewarded. Face the joyful embrace of death that all Totenkopfs desire."
—Simon to Caliban

The Master's predictions had been correct: the Proninist Party and the Rebels came to an agreement and joined forces with various factions to form the Crimson Coalition. Simon became the representative of the Totenkopfs in Trinity Gask, and he used his position to get close to Commander Glaurung Losstarot and her son, Hannibal Losstarot. He made twin Totenkopfs named Benedick and Beatrice his closest minions during this time.

Simon also manipulated Caliban to become his mole in the Coalition and soon found him useful when the Mullencamp were sent to capture the trespassing Fellowship of Maar Sul. Caliban followed Simon's instructions and slew his commanding officer Tybalt during the frantic chase and framed the fellowship for the murder. The plan worked as the fellowship escaped to Alent and thus could not deny these accusations. As a result Hannibal, grieving the death of Tybalt, sent the Vulfsatz after the fellowship and appointed Caliban as his new bodyguard.

When a group of Scuns led by Craig Rimner joined the Coalition and caused quite a fuss in Trinity Gask, Caliban used Hannibal's curiosity to supposedly lead him to see the Scuns but in fact took him to a secluded room where Simon, Benedick and Beatrice were already waiting. When the young Losstarot realized what had happened, it was too late: he was knocked out and taken out of Trinity Gask to a safe place which Simon himself had chosen.

Simon rewarded Caliban for his services by mercilessly killing him and then used his death and a forged letter as a means to make the Grand Alliance look like the culprits. He hoped that Glaurung would accuse the Alliance of the deed and begin a destructive war, thus furthering the Master's grand plan.

Everything once again proceeded exactly as the Master had foreseen when Glaurung indeed reacted terribly when she heard the news. Simon played the part of a concerned advisor and stayed in Trinity Gask while no one in the leadership of the Coalition knew of his involvement in the kidnapping. He became to view himself as a master tactician, and he pondered the possibility to actually take the Master's place as the leader of the Totenkopfs now that he had Hannibal as a valuable bargaining tool with which to manipulate the leaders of the Crimson Coalition. He chose to wait and ensnare everyone into his web of deception.

Sowing Season[]

When Jono Renfield and Vaetris Redfield brought Hannibal back to Trinity Gask, Simon wasn't pleased. He immediately took Zenobia to his quarters and asked her what had gone wrong. Luckily Simon managed to use his eloquent tongue to slither out of a dangerous situation and managed to pacify Glaurung for the time being. He knew that sooner or later Glaurung would figure out the Totenkopfs' true goals, so he had to act quickly. He began preparations to set his plan in motion, but he had to put it on hold when he heard that a pack of demons were attacking Trinity Gask.

Devourer's Reach[]

Simon later found out that the demons had somehow subdued and kidnapped Glaurung, and he realized that this was the chance he had been looking for. Using the ensuing chaos to his advantage, he made Zenobia tell the truth about the demons' attack but also mix in lies that the demons were working for the Alliance. This would fuel the Coalition's hate and would keep the conflict between them and the Alliance going. Pleased with the resulting discord, Simon took Zenobia with him to the Losstarot manor, ready to set the next phase of his complex plan in motion.

Deceiver's Gambit[]

More info later.

Heart of Darkness[]

Once a group of adventurers had been saved from Malperdy and were brought before Hannibal, Simon was present to observe the events. He made a deal with one of the adventurers, Razravkar, and offered him a chance to break free from the Coalition's yoke if Razravkar helped free the captive necromancers in Alent and guide them to the Coalition. He also offered Razravkar some cryptic advice how to get to Alent quickly although he left him much on his own to test his resolve and cunning.

Once the meeting with Razravkar had concluded, Simon went to oversee a process which would make Sloth the Coalition's spy within the Eastern Horde: he and Endoran put a collar, a similar one used on demons during the Magestar battle, on her. The collar would force the demon to magically obey their commands. Once the process was complete, they told her what she had to do and then set her free.

Despair's Wake[]

Simon received news of the death of one of the Totenkopfs, Breivik, and knew that the Totenkopf's mission to infiltrate the remnants of the Clergy of Gaea and the Clergy of Heath had been a success and that the resurrection ritual had gone as planned. He ordered his minions to track down the resurrected woman who was now their target, and he then chatted with Endoran about their future plans for various people in their scheme.

Aliases and Nicknames[]

What everyone calls him. It is unclear whether it's his real name or just a pun on the "Simon says" game because of his oratory skills.


An unkempt man who looks intimidating. Dressed in black Totenkopf robes.

Personality and Traits[]

A manipulative chessmaster.

Powers and Abilities[]

Very good with words and is able to twist half-truths or even blatant lies to make people do what he wants. He is quite skilled in playing chess. He prefers not to fight if possible, instead being content with manipulating everyone from the shadows.


Arbriel Conrad[]

Simon saw potential in Arbriel and managed to convince him to meet with Cain. This alliance proved to be useful, and thus Simon is partially responsible for the later Plague of Undeath which Arbriel has released in Remon.

Boris Ivanov[]

Simon used his speech to make Ivanov and the Proninists see things his way. He pulled the right strings at the right time and thus directly contributed to the forming of the Crimson Coalition as the Rebels and the Proninists formed their infamous alliance. Ivanov and Simon tolerate each other, but Ivanov is experienced enough to see that Simon is a dangerous man who shouldn't be messed with.

Cain Highwind[]

The only person apart from the Master who can control Simon is Cain. The likely reason for this is that Cain is an imposing and strong figure whereas Simon has a much more diminutive frame. Still, the two men never had such an animosity as Zenobia and Simon had, and Simon seemed to enjoy working with Cain who let him do what he wanted for the most part.


Calibal thought that he would become rich and powerful by helping Simon. Little did he know that Simon was only using him as an expendable plan in a greater game.

Endoran L'Sarius[]

Simon and Endoran have collaborated on occasion as they've seen how useful alliances can be to reach common goals. However, there's tension between the two as Endoran keeps belittling Simon who likewise snarks back at her. Despite this back-and-forth banter, both know that the other one is a cunning opponent who should not be crossed least as long as it's beneficial to stay in good terms with him or her.

Kamen Grimgaze[]

Simon holds the Master in high respect because the Master made him see the world in a new light. However, he has recently begun to ponder whether to use his talents in servitude or use them to carve his own path than the one the Master has envisioned. Simon has chosen to wait and see what the Master has in mind before making his move.


Simon and Zenobia are at odds because both have ambitious plans. The only thing that has kept them from going at each other's throats is Cain but now that Cain is busy following the Grand Alliance, Simon and Zenobia can renew their rivalry if they wish to do so.

See also[]