Timothy is a confident and conniving man. He is said to be very intelligent, second only to the youngest, Tilly. Although considered to be the successor, the strange suicide of his father left him to hastily ascend the throne. Unable to cope with the pressure and oppression from his siblings, he makes increasingly unreasonable demands with little regards to his soldiers and people. Even when realizing the intentions of the Church, he continues use of their pills and attacks with brute force despite foreseen consequences.
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 royal assembly he criticized Langley for capturing innocent women and their cruel treatment in prison. He ordered chief witch hunter to verify if arrested woman is a witch first before interrogation and restrict subordinates otherwise he would be thrown in the moat. He asked Lauren Moore to pay compensations to hurted women or their families. News of none of his siblings going to return displeased him greatly. He counted on Tilly and her superior intelligence, her missing puzzled him. 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 queen.
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.