|“||Don't forget who runs this city...||„|
|~ Dermot Quinn, Story Trailer|
|“||Don't be a stoat, Mr. Iraq! Where I grew up, we shot them between the eyes...||„|
|~ Quinn threatens Iraq|
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.
Events of Watch Dogs
After hackers Aiden Pearce and Damien Brenks attempted to hack into the Merlaut Hotel, which happens to be the Club's headquarters, but fail after Aiden left when a second hacker entered the system, Lucky, believing them to be after blackmail he held on Mayor Donovan Rushmore which depicted him murdering Blume Security employee Rose Washington, had a hacker named Clara Lille identify them. He then ordered Delford "Iraq" Wade, head of the Black Viceroy gang, to have Maurice Vega hit Aiden's family and another hitman cripple Damien, not knowing that Iraq was the second hacker as he didn't realise there was one. This resulted in Maurice killing Aiden's niece Lena Pearce, setting the events of the game in motion as Aiden vowed revenge on Maurice and whoever hired him.
Lucky first appears as a seemingly unimportant character in the mission "Backseat Driver", in which Neil Corrado, a henchman of the Club who killed his partner while trying to escape from a heist gone wrong, calls Aiden to drive him to a specific alleyway, which he was told to do by his fixer friend Jordi Chin. At the end of the mission, Aiden reaches the alleyway, where an old man who Corrado recognises as Lucky is waiting for them. Corrado gets out, and tells Lucky that, while he killed his partner, he still got what they were looking for. Lucky seemingly accepts this and takes the item that Corrado stole, only to suddenly order his bodyguard to kill Corrado. The bodyguard then slams Corrado against Aiden's car, allowing Lucky to stab him in the throat and kill him. Lucky then tells Aiden that he'll contact Jordi if he needs anything.
In "Grandma's Bulldog", Iraq gets an annoying call from Lucky, who accuses him of stealing the guest list for his sex slave auction. Although Iraq dismisses this as business, the call sufficiently annoys him to cause him to beat a random Viceroy to death.
In the mission "Risky Bid", Aiden, posing as psychopathic mob boss Nicholas Crispin, infiltrates Lucky's sex slave auction to hack Iraq's access card so he can infiltrate Iraq's hideout, and to rescue sex slave Poppy, who Crispin was going to buy. Lucky gives Aiden Poppy, and the two embrace, before Lucky recognises Aiden. He pretends not to, but then has his guards try to eliminate Aiden, but he escapes and has the police raid Lucky's auction, although Lucky and Iraq manage to escape.
Lucky's final appearance is in the mission "No Turning Back", in which Aiden goes to the Merlaut to kill him after discovering he had his niece killed. After killing most of Lucky's men, Aiden reaches Lucky, only to be taken prisoner while Lucky asks him why he came. Aiden tells him that he had his niece killed, which Lucky dismisses as a "little problem" before leaving Aiden to be killed by his men. However, Aiden manages to kill them and chases Lucky, fighting his way through hoards of Club members to reach him. After killing all the remaining guards, Aiden reaches Lucky's safe room, where he is unable to reach Lucky. However, as Lucky taunts him, Aiden hacks into his pacemaker, causing Lucky to collapse. Lucky then admits why he ordered the hit, showing Aiden the video of Rushmore committing the murder,before seemingly recovering. However, Aiden hacks his pacemaker again, finally killing him. However, it's then revealed that Lucky ordered the assassination of Clara, who was now working with Aiden. Despite Aiden's attempt to stop the hit squad, they gun Clara down, meaning that Lucky managed to commit one last villainous action after his death.
Personality and 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 includes sex slavery, human trafficking, drugs and numerous technology based crimes possibly including identity theft and fraud. He covers all of these crimes by appearing to be a generous and altruistic 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 cutting 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 seems to have some affinity towards the old-school gangster ways of the past, made evident in his gang meet ups and briefcase swapping. It is possible that Iraq is one of his proteges.