City Hall and Mayor Rogers himself is a constant thorn on Jack's side for the majority of the game, demanding that crime is kept low and favours they ask are answered. These requests are made through his deputy, Troy Starr, who is in fact a mole planted by Eugene Chaffee.
Events of This Is The Police
His decision to fire Jack Boyd in favour of his son-in-law Kevin Paulsen is the catalyst for the events of the game. He has held his position as mayor for some time and has no intention of giving up, despite being in his 80's. He is a corrupt and openly nepotistic politician who gives positions to family members or chosen favourites to further his agenda. He is also a confirmed rapist, after Jack, in a call with Lana Berman, learns that Rogers had raped her as well, while also revealing that other women around Freeburg who - at the time of the call were victims of The Dentist - were also raped by Rogers.
In the third act of the game, as an election approaches, Jack will side with either Rogers or Chaffee. After aligning with Chaffee, Jack will order an assault squad to storm City Hall and kill Mayor Rogers in a fierce gunfight, part of Chaffee's plan to take over as Mayor. Jack will still be fired from his position, but Chaffee will reward him with "enough money to last Jack the rest of his life" - one dollar. However, regardless of Jack's allegiance, Chaffee will sabotage Jack and Lana's relationship, claiming that "it had to be done". This will have severe consequences later for both Jack and Lana.
If Jack sides with Rogers, he must storm Chaffee's restaurant and slaughterhouse complex and kill him. The result is similar, as Jack will still lose his job. However, Jack will be able to keep the money he saved for retirement.