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Why does Willis assist Matt in seeking revenge?

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Willis is a WWII veteran and a man who has built a successful business on his own merits. Willis is a family man, just like Matt, and he listens carefully when Matt tells him how hard things are for his wife, Ruth, in the wake of their son's death. He is a sympathetic and supportive friend to Matt, and he does not believe that the judicial system is always fair. This is evident in his remark about a previous murder:

Remember that woman about seven years ago? Shot her husband and dropped him off the bridge in the Merrimack with a hundred pound sack of cement and said all the way through it that nobody helped her. Know where she is now? She’s in Lawrence now, a secretary. And whoever helped her, where the hell is he?

Willis does not believe that the perpetrators of that crime paid their debt to society. Moreover, Willis is no fan of Strout, the young man who murdered Matt's son. Willis knows Strout, and he tells Matt, “I hate him, Matt. My boys went to school with him. He was the same then." Willis has heard that Strout is out on bail, and he believes that Strout will not serve more than five years for the crime of killing Matt's son. Clearly, he finds that thought unacceptable and, without much conversation with Matt, makes his decision to help Matt get the justice that he does not feel that the court will offer.

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This becomes one of the most interesting elements of the narrative.  There is little in Willis' character to indicate that he would be privy to being such an agent of violence.  However, there are elements to his character which operate upon him, causing a pivot to being a collaborator in a heinous crime.  Willis is a part of the town gossip machine.  When Matt comes to him in an emotionally broken state, Willis does little to assuage Matt.  Rather, he helps to fuel his condition with talk of unsolved murders in the town, the easy access to guns, and revenge.  

In a way, being privy to the town gossip has enabled Willis to easily enter into a domain that previously would be unthinkable.  Being able to live out the elements of gossip through Matt's grief and banking on it to fulfill these tendencies is where Willis is able to help Matt.  When Matt begins to engage in some level of doubt about the implications of what he is to do, Willis is steady and resolute in following the plan of  premeditated murder.  It becomes clear that Willis is helping out Matt in understanding his pain.  Yet, a part of the reason he is able to do so is through his role in the town's gossip machine in which information and innuendo are taken to mean more than what they might.  As opposed to being a force of moral clarity, Willis is really no different than any of the other main characters who operate in a realm where moral ambiguity reigns supreme.  

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