Caesar despises Jillian, whom he privately refers to as "the Wack from Faq", and is strongly opposed to Don King's policy of rapidly building the strength of Faq. Jillian dislikes Caesar because he was unwilling to give her the opportunity to find and croak Stanley.
Caesar's personal troubles began when he was assigned to meet with Count Vinny and a Barbarian Mercenary named Jillian. Jillian had made what Caesar regarded as the highly improbable claim that the ruins of three previously undetected cities existed close to Transylvito, and that Stanley planned to rebuild these cities after Gobwin Knob fell. Don King sent Caesar and a group of Warlords to investigate, to croak Stanley if he arrived where Jillian said he would be, and to claim the three cities for Transylvito, if they actually existed.
Caesar was deeply suspicious of Jillian from the beginning, and made it clear that he was in charge. Jillian and Caesar quickly developed an antipathy for one another. Part of the problem was that, unlike Vinny, Caesar was not particularly friendly towards the members of the RCC, and frankly seemed to care little about Stanley one way or the other.
Stanley did indeed make an appearance, but Caesar's ambush failed to croak him, because of Foolamancy and the combat power of the Arkenhammer. Two of Caesar's Warlords were croaked. Jillian then demanded that they pursue Stanley, but Caesar rejected her demand, because they would never find him while he had a Foolamancer. Caesar intended instead to claim the three ruined cities as he had been sent to do. Later when he informed Jillian that Ansom and all of the other members of the RCC army had been mysteriously croaked, she attempted to croak him in a fit of rage. If not for Vinny's interference he probably would have croaked her on the spot.
He may have regretted not doing so, because the next morning he received a change of orders from Don King. He was now ordered to escort Jillian to Transylvito, and to treat her as a Royal as he did so. Whatever dealings Caesar had with the two Royals who preceded him as Heir had left him with a rather low view of Royals in general, so he followed his orders from Don in the most sarcastic way possible. When he arrived in Transylvito, he learned that Don not only intended to allow Jillian to claim the three city sites, but to give her a significant amount of money to rebuild them. This was only the first of the money transfers to Faq which Don has authorized, and to which Caesar is deeply opposed.
When Jillian left the battle for Jetstone, Caesar ordered Vinny to begin listing every military asset Faq had. His current intention is to take the side.