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- "Cut the shit fat-man. I known guys like you my whole life, killed most of 'em, you ain't never seen a throne you didn't want to sit in. So I'm here to make myself crystal clear, there's only room for one of us in this prison and it ain't gonna be you, not ever. Because I'm the Kingpin of this bitch."
- ―Dutton to Wilson Fisk
Dutton gained a reputation as a powerful and feared drug dealer in New York City, killing anyone who attempted to surpass him. When Dutton attempted to make a deal with the Blacksmith, a dealer with a line of pure heroin shipped in from the far east, Dutton called on the Kitchen Irish, Mexican Cartel and the Dogs of Hell to meet in Central Park for the deal. As tensions raised the groups realized that the meeting was a sting by the FBI and the Blacksmith did not show up, leading to a gunfight which killed several civilians.
Running Ryker's Island
- "You may have made a name for yourself on this outside, but I run the big box. I just wanna make that clear, in case you got any ideas about stepping up."
"I have no intentions of doing that."
- ―Dutton and Wilson Fisk
Dutton was arrested for his crimes and was locked up in Ryker's Island. However using his vast wealth and criminal mind, Dutton was soon able to take control of the prison, buying out the guards and controlling the shipments of illegal contraband which came into the prison, amassing a large profit and a loyal band of followers in the process. Because of his new power Dutton began calling himself the Kingpin.
When Wilson Fisk was arrested by the FBI with the assistance of Daredevil for running a successful and violent criminal empire in New York City, Dutton decided to pay him a visit and introduce himself, although Fisk made it clear that he already knew of Dutton by his reputation alone. Dutton threatened Fisk, telling him that while Fisk made have had a position of power on the outside he needed to understand that Dutton was in charge of Ryker's. Although Fisk claimed to have no interest in stepping up Dutton did not believe him and warned that he would never run the prison.
- "This crusade of yours, it's never gonna end right? Right?"
"Yeah, yeah you're right."
- ―Dutton and Punisher
While counting his money with another inmate, Dutton was suddenly attacked by Frank Castle, who cut his man's throat before pushing his knife into Dutton's gut. Castle demanded to know about Dutton's involvement with the Massacre at Central Park where his family had been killed in the crossfire. Dutton explained he was doing a deal between the Kitchen Irish, Mexican Cartel and the Dogs of Hell, he then gave up the Blacksmith's name but Castle stabbed him through the gut regardless and let him bleed out on the ground.
Dutton was kept alive by the prison doctors and put on life support, but as he lay in his bed he was visited by Wilson Fisk, who sat beside his bed and ate dinner. Fisk revealed to Dutton that he had arranged for Castle to assassinate him and explained that very soon Dutton would drown on his own blood, telling him that he had taken his earlier words to heart about there only being room for one Kingpin in Ryker's Island. Eventually Dutton died of his wounds in his hospital bed, giving Fisk control of the prison.