Simon Whittaker works for Tarvos Security Services as Head of Operations in Prague. He is the brother-in-law of Ivan Berk, who was responsible for the bombing of Růžička Station in 2029. Whittaker is encountered at the Tarvos Prague headquarters in Desperate Measures.
Sometime before the bombing of Růžička Station, Whittaker was working on trying to get Ivan, and therefore his sister Melissa, out of Golem City. At one point, Ivan had submitted a licensed consultant application as a way to try and get out, but it was "deep-sixed" by someone high up enough in city politics that Whittaker was told to stop asking about it.
After the bombing of Růžička Station, Whittaker was contacted by Melissa, who frantically explained that she knew Ivan was responsible for the bombing. Deciding on a course of action, he corrupts the station's camera footage so he can protect Melissa. In doing so, he also bribes an employee at Růžička Station, Pavla Keilmanovich, to keep quiet.
Adam Jensen learns from Pavla that someone from Tarvos tampered with the footage. Jensen heads to the local Tarvos headquarters to investigate further, eventually confronting Whittaker. If Jensen is able to uncover evidence of Whittaker's involvement, Whittaker will admit to his wrongdoing, but state that he corrupted the footage only to protect Melissa.
- He is voiced by Julian Casey, who also voiced Garvin Quinn.
- In Simon Whittaker's office, there is a picture of a British Army General with two children, which (based on his epaulets) was taken sometime during the reign of Queen Elizabeth II. The General is likely his father, and the children Simon and Melissa.