55 pages • 1 hour read
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Throughout the book, Wilson portrays how structural systems of oppression inhibit personal development and community health. Wilson says that Maryland Governor Parris Glendening’s 1995 ban on parole for life prisoners both fueled and reflected the “super-predator panic of the 1990s,” which began “stacking young black bodies in prison cells” (123). Keith Showstack, Wilson’s lawyer, commends Wilson for his “incredible” record of self-improvement inside prison but also advises patience until the “political climate” is more favorable for his release (163). Meanwhile, Wilson takes a class in modern American history and learns methods by which “black poverty was planned” (171). He feels queasy inside courtrooms, which he describes as “the places America created to finish us off” (218). Even returning citizens, former inmates who have served their time and earned their freedom, stand little chance of success, for the justice system “is a vacuum, designed to suck money out of the pockets of the people struggling the most” (276).
Wilson develops an early distrust of the police, starting with his mother’s boyfriend. When police are called to Mom’s house during one violent incident, Wilson learns that “cops took the aggressive approach with a black man unless he was one of their own,” and things “always ended the same way: no report, no arrest, just a night away to sober up” (25). He says that when Wilson’s friend Little Anthony was shot and killed in Washington, D.C., the “cops stood around his body for hours. It wasn’t an investigation; it was a message. Just another dead black kid. That’s what he gets for living here. That’s what you animals deserve” (47). Within the first two years following his release from prison, Wilson is pulled over in his Corvette 26 times. Wilson estimates that “[n]inety percent of cops were good people, but there were enough assholes to make it a grind, especially when aggression was being encouraged from the top” (342).
The prison itself represents another imposing and often-corrupt symbol of oppression. After approving Wilson’s plan to start a photo business and deposit its profits into the youth program, for instance, prison administrators renege on their promise and instead use the money to buy new security cameras. Likewise, Wilson’s caseworker in the halfway house routinely harasses him and even tries to provoke him into retaliation by blaming him for his mother’s suicide. And prison administrators adopt a policy of delay and resistance in response to Judge Serrette’s order reducing his sentence from life in prison to 24 years. Wilson reflects on prison administrators’ decision to resist Judge Serrette’s ruling by saying, “So why did they turn on me? The answer is the system. Once you’re in the system, you’re no longer a human being to them” (237).
Wilson frequently refers to Plato’s famous allegory wherein “people live chained in a cave. They see only light from torches and shadows on a wall, so they think shadows are reality. When one person escapes and goes out into the world, he realizes he had only seen illusions. Wilson notes, “Even at eight years old, I knew the story was about me, because I was living in that cave” (13-14).
As an adolescent, Wilson lives on Division Avenue in Washington, D.C., a self-contained world of eight or nine blocks bracketed by a pair of housing projects. He says that everyone carries a gun “because young black men were dying in the streets,” and “you don’t question it, because that’s the cave” (29). When a counselor asks Wilson why he is trying to kill himself, Wilson responds, “I’m not trying to kill myself, fool.” Rather, he was “just trying to survive” amidst the violence (37).
The cave follows him to Patuxent. In the dayroom, inmates erupt in wild enthusiasm when the local news features reports of murders in the inmates’ old neighborhoods. On the streets, Wilson had learned to look the other way when he knew something bad was about to happen, and he takes that same approach at Patuxent when he knows that one inmate is about to attack another: “That’s prison. That’s the neighborhoods. Staying quiet isn’t about protecting bad people or sticking with our own, it’s self-preservation. It’s the only way to get out. If you don’t understand that, then you don’t understand our world” (193).
In therapy, Wilson learns to feel remorse for his crime by imagining the incident in the context of the cave. Research reveals that the man Wilson killed was in his early 30s and had spent much of his life in housing projects and in trouble with the law. Beyond that, Wilson finds very little, but the lack of information about the man he killed, coupled with the fact that no one spoke for that man or even appeared on his behalf at Wilson’s trial, leads Wilson to one important conclusion: if the man had family and friends, they all “walked away when he died,” which means they “were in the cave,” so Wilson’s victim “must have been living there, too” (203). Wilson imagines “[a]ll the people who had to abandon him for him to bleed out alone in that grocery store doorway” and then pictures him “scared and bleeding, probably crying for his mom” (204). In short, Wilson feels empathy when he views the man he shot not as an enemy but as another victim of the cave.
Wilson says that from the moment he decides to take control of his life, he was on his way out of the cave. The day after he creates his Master Plan, he runs five laps around the prison yard, lifts weights, showers, brushes his teeth, and even checks his fingernails because “[p]ride is in the details” (108). Every day he sticks to his Master Plan. He enrolls in carpentry, reads W.E.B. DuBois, and combines lessons from both sources in a way that deepens his understanding of his goals. He meets Tooky and other “old heads” in carpentry who “were craftsmen” and “had pride” (120). He reads DuBois on the “‘aristocracy’ of labor” and the “importance of doing simple jobs right” (148). He concludes that “it’s the craftsmanship that counts,” for it provides “a sense of purpose and accomplishment nobody can take away, no matter how hard they try” (149). When he meets his lawyer, Keith Showstack, Wilson says: “I want my life to mean something” (161).
Having established his goals, Wilson shares his Master Plan with other inmates. At Patuxent, he transforms the career center into a “workshop on creating a Master Plan” (246). The crux of his message to inmates is threefold. First, they must not be a burden to their families. Second, they must do the necessary work while still incarcerated so they can be prepared for life on the outside; not all inmates have life sentences as Wilson does, so they could look forward to freedom. Finally, Wilson asks “What’s your endgame?” “How do you want to be remembered” (247)? Few young men ever imagine their own legacy, but Wilson forces them to think about it because legacy is the basis of the Master Plan.
When he leaves prison, Wilson never loses sight of his goals and even applies the concept of endgame to broader contexts. After Baltimore’s April 2015 uprising, Wilson identifies the problems facing the city: “guns, poverty, policing, racial stratification, over-incarceration, and lack of opportunity.” Then, he asks, “What’s our endgame” (360)? Wilson acknowledges that the problems are complex. Still, the endgame is the lens through which he views possible solutions.
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