Dermot "Lucky" Quinn

"Don't forget who runs this city..."

- Dermot Quinn, Story Trailer

Dermot Quinn a.k.a "Lucky" Quinn is the leader of the Chicago South Club and the one who ordered the hit on Aiden Pearce and Damien Brenks during the game's prologue, which resulted in the death of Pierce's six year old niece, Lena. He made a deal with Blume agreeing to co-finance CtOS in exchange for backdoor access to the entire city. Quinn is the secondary antagonist of the 2014 video game Watch Dogs.

Description
Lucky isn't a pampered mob boss - he fought for everything he owns and he's still fighting. He's an intense, imposing man who has survived countless attempts on his own life. As head of the Chicago South Club, Quinn knows embracing technology is what elevates his operation to unparalleled success in the criminal underworld.

Personality/Traits
Quinn is the most powerful and ruthless crime boss in Chicago. Quinn is shown to be the head of a large crime syndicate which inlcudes, sex slavery, human trafficking, drugs and numerous technology based crimes possibly including identity theft and fraud. He covers all these crimes by appearing to be a generous philanthropist.

He also invests in and owns various businesses, such as The Merlaut Hotel and his own Marina. A conniving individual, He is not against blackmailing other people and cut deals with organizations to further increase his standing and influence over the city like he did with Mayor Rushmore and Blume and lacks a moral compass as shown by his partaking in human trafficking and his indifference when being confronted by Aiden on his implications towards Lena's death.

He also semms to have some affinity towards the old-school gangster ways of the past, made evident for his gang meet ups and briefcase swapping.