Fisk convinced a newly-arrived Frank Castle to murder Dutton due to seemingly having a role in the Massacre at Central Park. Unbeknownst to Castle, Fisk also planned to have the rest of the inmates take care of him after he killed Dutton. Castle managed to survive the attack, leaving only part of Fisk’s plan fulfilled.
- "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
Soon after being incarcerated at Ryker's Island, Wilson Fisk was approached by Dutton, a powerful drug dealer who ran most of the contraband in the prison. He warned Fisk that although he made a name for himself on the outside, it was Dutton who ran the prison.
When Finney brought Fisk a newspaper covering the trial of Frank Castle, Fisk noticed that the Punisher had targeted members of the Dogs of Hell, a group with whom Dutton had dealt with before. He began to formulate a plan to get Castle to the prison to kill Dutton.
Frank Castle, armed with a shiv given to him by Stewart Finney, entered Dutton's cell block and easily killed the men who were with him. He interrogated Dutton until Dutton told him all he know about the Massacre at Central Park. Dutton confirmed that the three gangs, the Dogs of Hell, the Mexican Cartel and the Kitchen Irish were there to meet with a mysterious drug dealer known only as the Blacksmith. However, the Blacksmith did not show up, and the gangs, riled, attacked each other. Castle then fatally wounded Dutton.
Although Wilson Fisk had promised Castle that the guards would let him out of the cell block after he was done, he betrayed him. The guards left the cell block locked but opened the individual cells while Fisk thanked Castle for his help.
The prisoners, after finding Dutton, attacked Castle, but he was able to brutally take them all out. Eventually, guards in full riot gear entered to take Castle away.
Wilson Fisk visited a chained Frank Castle and admitted that he had underestimated him. He told Castle that he was helping him escape so that Castle could eliminate the rival crime factions in New York City, so that when Fisk was released, the city would be his for the taking. At first Castle was furious at Fisk for setting him up and attacked him, but being wounded and chained, he was no match for the ferocious Fisk.
Eventually, Castle accepted Fisk's help, although he warned him that the next time the two of them met, only one would walk away. Fisk replied that he was counting on it.
Castle escaped while disguised as a guard.