- "It's amusing the Demon's Head thinks he can catch my employer unaware."
- —Damien Darhk's assistant to Oliver Queen[src]
In early 2015 Damien Darhk visited Starling City and stayed in at a hotel of which he had the entire top floor shut down and guarded by his operatives. It's unclear what his intentions were but Damien caught on early that Ra's al Ghul was planning to destroy Starling City with the Alpha-Omega bio-weapon to kill him. He escaped, leaving his Ghosts in the hotel, along with his assistant, who posed as Darhk.
Oliver Queen intended to capture Damien Darhk and give him over to Ra's in exchange for sparing the city from the virus, only for the assistant to surprise Queen with a revelation: the real Darhk has already left. The assistant was amused by the situation, only to get shot by an arrow from one of the League of Assassins members. Ra's phoned Oliver after the debacle, praising his "bold move", yet threatening Queen at the same time.
Damien Darhk's assistant was a confident man with a sense of humor. Threatened by the Arrow, he only thought to comment on the fact that the hotel was going to bill him for the broken window. His overconfidence proved to be his weakness as, distracted by his banter with the Arrow, the assistant was not able to evade the assassin's arrow.