Timothy Wimbledon was the second prince & self-proclaimed fourth king of the Kingdom of Graycastle.
Timothy is described to have been attractive, with short and curly gray hair and eyes. Timothy was also suggested to not have been as strongly built as Gerald Wimbledon, but was not suggested to be diminutive in stature.
Timothy often was viewed as confident, charismatic, and held a regal composure fitting of a Monarch.
Timothy Wimbledon was often portrayed as a supremely confident, charismatic, and oft conniving individual. At many occasions, he was described as intelligent by many and stood second only to his youngest sister, Tilly. This intellect allowed Timothy to discover the Church's plot against the Kingdom of Graycastle far before many others fully grasped the situation and it is briefly suggested he may have been able to succeed had it not been for the interference of his siblings.
Due to his impressive cunning wit and ambitious actions during his early life, Timothy was widely regarded as being the true successor over the throne. This realization likely played a key influence in Timothy's personality as he was later depicted to have frequently engaged in acts of supremacy over those he deemed lesser. This primarily targeted his younger brother Roland, whom was the frequent target of often brutal and cruel acts by Timothy, Gerald and Garcia.
It is also likely due to his position that this personality tendency was never corrected, as neither his father nor overseers seemed to have taken any action against Timothy for his crueler tendencies. This also spilled forth in Timothy's seeming disregard for life in his later years as Prince and then King of Graycastle.
Timothy was not entirely bad nor corrupt, however, as he was frequently depicted as showing favor to those who served him effectively or loyally. He was also shown to have at least some ability to forgive failure, but was vicious to those who were incompetent, and cruel to those who were not totally loyal.
It is also strongly suggested that the Challenge of Succession may have affected Timothy's disposition and that of his siblings in their pursuit of Kingship. This division likely effected Timothy as a psychological level and only furthered his tendencies once his siblings became enemies and the throne became a prize. Further adding the serious and sudden suicide of his father right before his eyes, it can be entirely likely that Timothy suffered some form of psychological trauma as a direct result. This can be extrapolated from his vicious lashing out against the population of Graycastle's King City in an effort to locate the potential Witch responsible.
This negative development within Timothy is likely what inspired many of his later actions during his subsequent days and reign. His haste to the throne led him to sacrifice his older brother Gerald as a murderer and his own reign of the Kingdom was shaky at best. Many times it is suggested the pressure and oppression he felt from his siblings, first Garcia, then Roland, increasingly affected Timothy's ability to lead.
As the turmoil that was the struggle for the throne build ever higher, Timothy began to make more and more unreasonable demands upon his subjects and soldiers which culminated in his merciless use of the Pill of Madness. His violent military campaigns against both nobles and his sister Garcia left much of over half of the Kingdom in ruins, with at least tens of thousands dead.
Likely from the stress and weight of leadership Timothy was unprepared to carry, his respect for life nearly vanished by the end of his reign and his violent and cruel tendencies came to a head with the use of suicidal soldiers. His great intellect was simply not enough to overcome the sheer dominance of his younger brother's, Roland, sheer technological superiority which led to his eventual demise.
When the city fell, Timothy is shown to have a minor breakdown as he nihilistically plots the destruction of his own Kingdom as he would rather the entire Kingdom burn rather than let any of his siblings possess 'his' throne. His plot to use the Church to this end, a bitter enemy of Timothy's by this point, shows his determination to inflict harm upon Roland who had stolen his power. This possessive and dominant passion would quickly vanish upon his capture and subsequent imprisonment. His ambitions and cruelty vanished as the consequences of his actions were brought against him and his mind began to fray. The proud Timothy fruitlessly begs for his life and weeps shamefully as he is death becomes certain.
Even though at the beginning, Timothy was shown to be a capable, confident, and ambitious prospective King, the weight and responsibilities of his reign led to his subsequent fall.
Timothy frequently harassed and bullied his younger brother Roland and is strongly implied to have been the root cause to many of the former Prince's vices and malicious behavior.
It is strongly suggested early on that Timothy was the favored son of Wimbledon III and destined for the throne ahead of his elder brother Gerald. Whilst his cunning was matched by both Tilly and Garcia, the latter two were females and thus not equally considered for the royal succession until the Battle for Succession.
Timothy tricked Gerald into his trap, making the latter look like a traitor who killed Wimbledon III for the throne. After executing Gerald, Timothy claimed the throne and the name Wimbledon IV. He gave the announcement to recall the rest of his siblings.
He started witch hunting being sure only witch could make his father kill himself despite Stone's protection. At the royal assembly he criticized Langley for capturing innocent women and their cruel treatment in prison. He dictated that his chief witch hunter was required to verify if an accused woman was a witch before interrogation could begin. Any disobedience to the royal decree would warrant the offender being thrown into the moat from the wall, likely with weight attached. He asked Lauren Moore to pay compensations to any and all harmed women or their families. News that none of his siblings had returned displeased him greatly. He had counted upon at least Tilly, and her superior intelligence, being the one sibling that would have returned. The news of Roland's decision to stay in Border Town Timothy viewed as his another stupidity. As for Garcia, her lack of response he considered direct refusal and asked premier minister to send orders to the Duke of Southern Region to capture her. At this moment "The Frostwind Knight" Naim Moor delivered news of duke's defeat and Garcia's declaring herself the The Queen of Clearwater.
Following this, Timothy and Garcia entered into a series of conflicts, eventually resulting in the frequent use of the Pill of Madness to supplement depleting manpower. Whilst Timothy initially suffered several setbacks against Garcia, he finally managed to push her back after suppressing several revolts and mustering his power. This led to the burning of Clearwater City and Garcia's flight from the Kingdom. The conflict between the two led to vast amounts of refugees as many of the Eastern and Southern territories had been left in ruins, with most population centers razed by the end of the fighting. Garcia's extensive raiding along the coastline following her flight only furthered the damage.
Following his victory over Garcia, Timothy spends much of his time consolidating power. He makes several overtures to Roland to surrender himself, yet is noted to not have the intent to kill him so long as he surrenders himself. Though, after the defeat of the Duke and his brother's ignoring of his generous mercy, Timothy makes several efforts to finish his brother once and for all.
By this point, Timothy has deeply ingrained the use of berserk soldiers induced by the Pill of Madness to fight for him. This was doubly to reduce the burden of refugees brought about by his and Garcia's conflict, and to avoid expending precious manpower and knights. Timothy strongly believed that a force of several thousand maddened soldiers would be more than enough to eliminate Roland's fighting force. Thus, he was all the more surprised when the force was completely annihilated by his previously incompetent brother. This led to Timothy growing partially paranoid over Roland's sudden development.
After a period of time consolidating his throne and stabilizing the seat of his power, Timothy eventually devised a plan to slowly drain Roland's fighting power through the use of more maddened soldiers. His plan was meant to dispatch a strong force of refugees under the control of knights to bypass Longsong Stronghold and directly attack Roland's seat of power in waves via the waterway. When this force was obliterated by the overwhelming power of Roland's First Army, Roland allowed survivors to return and spread the word of their defeat and a looming attack by Roland. Timothy largely dismissed the latter threat and focused on the idea of Roland's new weapons that allowed him to destroy the fleet he had dispatched.
Around this time, the secret of blackpowder made its way into Timothy's possession, leading him to believe that this weapon was what led to Roland's string of victories. This all the more frustrated Timothy as his city's blacksmiths were unable to produce effective models of the weapon and he frequently lamented over the weapon's dangers and inefficiency. Yet, convinced that this technology was what gave Roland such an edge in warfare, Timothy wisely invested into blackpowder technology and forced the Alchemist Guild to continue and expand producing and research into blackpowder and its uses.
Timothy's confidence was dealt a near fatal blow, however, as Roland's threat to attack the heart of King's City came to fruition with the destruction of King City's dome. Whilst Timothy's investigation eventually led to the discovery Roland had means to attack from the air, he was left in the dark as to how his brother had achieved this as well as how his brother had such destructive weaponry at his disposal. This attack firmly led to Timothy believing his brother had sold his soul to the demons in exchange for their aid in destroying the Kingdom, and this reasoning was supported by Roland's employment and open support of Witches.
Seeing that a direct confrontation was unwise until he had managed to close the technological gap between himself and Roland, Timothy devised a tactic of attrition with his younger brother. He dispatched a force of raiders and pirates to blockade the Western region from imports in order to cripple their highly import-dependent economy and quite literally starve them into submission. This tactic would, in all hindsight, hasten his downfall as Roland would expedite his plans to topple Timothy upon the realization of his brother's ploy via his intelligence network.
Timothy made plans to muster his full forces and destroy his brother when he was fully prepared, however, Roland would attack during the middle of the planting season. This would catch Timothy nearly defenseless as his blockading forces were annihilated and most of his soldiers were disbanded to sow the harvest. As Roland's economical structure let the First Army be independent of the harvest, he was able to strike Timothy when his defenses were at their lowest.
King's City had critically few defenders to sustain a siege against Roland's highly advanced weaponry. Whilst Timothy showed remarkable ingenuity with the use of blackpowder warfare and booby traps, including the use of landmines which reflected his great intelligence and cunning, Roland's use of vastly more modern weaponry and employment of witches completely negated Timothy's efforts. A critical strike from the air breached the castle walls less than a full hour into the siege, and the castle itself fell within less than a day.
Whilst Timothy managed to temporarily escape, planning to conspire with the Church to bring Roland to ruin, Roland's use of witches allowed him to locate Timothy before the latter could escape and imprison him.
Roland would go on to imprison Timothy in the very cell that Timothy had imprisoned Roland in all those years ago. The realization that he had been defeated and Roland's extreme and dramatic changes led him to accuse Roland of selling his soul to the very end. Whilst Timothy had made very logical arguments and had access to rare information that would have normally saved his life until he could formulate an escape, Roland's vastly superior information network had already uncovered more information than Timothy due greatly in part due to the discovery of the ancient witch Agatha.
Timothy broke down greatly as his pride and ambition, which had largely allowed him to withstand the shock and stress of rulership, and he is depicted in desperation in his final moments.
It is largely considered 'fan-canon' that Timothy wept sorrowfully as he was executed by hanging before the gathered crowds of King's City for his many crimes against humanity by his brother Roland.
Timothy is very intelligent, capable of predicting and controlling the movements of his older brother and taking advantage of the latter's plans.
It was noted the the two were close when they were younger. Initially unwilling to kill him on the account of their past relationship, he decisively ordered his execution after the unexpected death of their father.
It was noted the the two were close when they were younger, often playing together in the castle gardens and showing concern over her well-being. Now, Timothy is pressured by her growing forces and strong desire of the throne leading him to forcefully deceive his people into taking pills from the Church to serve as cannon fodder in order to enforce his rule. He views her as an obstacle and actively tries to kill her.
Timothy was never fond of Roland, taking pleasure in making his younger brother's life miserable. He often thought of him as a useless fool even after the successful defeat of the Duke. Once, he locked him in the castle dungeons and neglected him only to return after taking delight in his pathetic appearance; the mocking that ensued caused young Roland's deeply ingrained fear and cowardice to follow him throughout adulthood.
- He first appeared in Chapter 45.