The Dentist

"""'You have such...lovely teeth. I look forward to adding them to my collection.'"-The Dentist to Sofia Falcone.

The Dentist  is a torture expert employed by  Oswald Cobblepot. His specialty is drilling and he is  obsessed with collecting the teeth of his victims.

He is seen torturing Sofia Falcone in Things Go Boom.

Biography
After Oswald Cobblepot confronted Sofia Falcone at her mansion, who finally revealed her true face to him. Penguin then told her that she will explain him the full extent of her plan including if her father Carmine was involved, which of his captains she has turned, and how she intended to rid him from the city. Victor Zsasz then ordered his men to bring "him" out, leading to the Dentist entering the hall. After Penguin and Zsasz left Sofia behind at her house, the Dentist strapped Sofia to a chair and started his torture actions by laying down all his dentist tools on a table and starting to check her teeth. After remarking her teeth as "quite lovely", he announced to her that he plans to put them in his trophy case. Sofia then asked him if he even knows who she is, to which he responded that he knows she is Don Falcone's daughter, since Carmine killed the Dentist's brother. He afterwards put on a drilling machine and turned around to his victim, telling her that he is going to enjoy this.

Sofia moved on to threat him by responding that there are still some people alive like his wife Elaine and his son Joseph and revealed that she knows their exact location. Surprised by her knowledge, the Dentist turned off his drilling machine, leading to Falcone to explain her torturer that she made it a point to learn every detail of the Cobblepot crime family, for instance that Penguin only trusts one man for this type of job, the Dentist. Moreover, she claimed that in the event that she is ever tortured her people have instructions to kill her tormentor's family.

However, even though he called her threat "interesting", the Dentist explained her that no one is going to know that she were tortured, beacuse no one is going to find her body, but Sofia replied by telling him that she has spies inside Penguin's organisation, though Cobblepot is right about her conspiring against him for months, turning his captains against him one by one and that today shall be the day that she will finally take him down, so if her people don't hear from her soon, the Dentist's family is going to be dead. Fearing the loss of his wife and son, the Dentist ordered a henchman Penguin left behind to observe the torture process to tighten Falcone's restrains and used the opportunity to surprise the gangster by drilling into the man's head. Afterwards, Sofia praised the Dentist's wise decision and commanded him to untie her.

Season 4

 * "Things That Go Boom"