The Master Plan Discussion Questions  

In The Master Plan, how is Wilson’s life affected by the structure of his family?

Family structure for young Chris Wilson is constantly shifting. He spends weekends with his mother and weekdays with his grandparents. His older brother and sister sometimes live with him, and sometimes they live elsewhere. His father is mostly absent from his life. Later, he’s mostly absent from his own son’s life. This unstable structure brings him a great deal of grief; loss is normative. In addition, the distance between himself and his family increases over time: his mother turns increasingly to drugs after she’s beaten by her boyfriend, and his sister rejects him because she wants to build a more stable life.

The unstable family life Wilson experiences has two important effects. One is that Wilson is still bonded to his family but in heartbreaking ways. For example, his cousin’s murder is one reason he begins to carry a gun and ends up using it. And his feelings of abandonment by his mother cause him years of pain and regret, especially after she dies. A second is that once he is imprisoned, his family is easily replaced by the men he befriends inside. He comes to consider them family. And that is not really a bad thing because his family relationships carry emotional baggage that isn’t very healthy, while his ties to his prison “family” end up contributing to his sense of purpose and self-worth.

In The Master Plan, how is Wilson’s life affected by racial injustice and discrimination?

Chris Wilson’s life is enormously affected by racial injustice, especially systemic racial injustice. It is clear that he is tried as an adult instead of a teen and receives a life sentence mainly because he is Black. He mentions that he is seen as a “super-predator,” a term that came into use in the 1900s and was applied primarily to young Black men. A super-predator is supposedly someone who is disposed to violent acts due to lacking a loving, moral upbringing. While statistics and analysis did not bear out this theory, the negative stereotype stuck and influenced a decade or more of prosecutorial and sentencing decisions.

In addition to this racial injustice in the legal system, Wilson’s life after he is released is marred by racial discrimination. He obtains the Corvette he always dreamed about, but he is regularly pulled over because police officers perceive a Black man driving a Corvette as a likely criminal. So he gives it up and drives a less flashy car instead.

Furthermore, the entrenched poverty and violence in his childhood neighborhood—and later in his Baltimore neighborhood—are due in part to racial discrimination in housing. Redlining, the practice of classifying some (usually Black) neighborhoods as not worthy of investment through loans and insurance, is an example of this kind of discrimination. Police brutality against Black people is another. Wilson comes to understand that many of the problems he faces are linked to the 200-year-old history of racial injustice in the United States, beginning with the enslavement of Africans and continuing to modern society.

In The Master Plan, how is Wilson’s life affected by the structure of the prison system?

Chris Wilson’s life changes drastically when he becomes part of the prison system. Inside the prison, he has to submit to a variety of daily humiliations. Guards have a lot of power and little accountability, and some hassle inmates for thrills. And when he is trying to arrange for a sentence reduction hearing, prison administrators continually obstruct his progress, some out of spite. This is because people enter the prison system due to a court system that, once a person is convicted, gives the power over their life to the prison administration, which generally works to keep people inside, regardless of whether they deserve to be imprisoned.

Other aspects of the prison system structure at Patuxent are forces for good in Wilson’s life, however. He is placed in the only youth program in the state, which was established to help rehabilitate young offenders. He is able to take advantage of programs inside this youth program to get his GED and learn languages and skills. He is able to join the Inmate Advisory Council, which advocates for prisoners’ rights. It is this highly structured youth program—which Wilson points out is unusual—that gives Wilson the tools he needs to thrive once he is released.

In The Master Plan, how is Wilson’s life affected by community dynamics?

Chris Wilson’s early life was shaped by his community, which was structured by both internal and external factors over which he had little control. As a child, his community was made up of his neighborhood and school—both of which were marred by the systemic racism inherent in the push for government housing projects, racist practices such as redlining, and a criminal justice system that disproportionately incarcerated Black men. Wilson’s young life is not structured by just institutions or by the rule of law but by neighborhood “crews,” gangs, and corrupt police officers.

Many of these organizing principles are also present in the prison system. While the court system sends people to prison, once there, prisoners sort into a hierarchy that places the prison administration in ultimate power but with gangs in charge of much of the inmate community. Within this hierarchy, Wilson tries to survive and ultimately thrive, but it isn’t a simple task. He has to not only work hard and stay out of trouble but avoid getting drawn into anyone else’s trouble as well. Over time, however, the prison community’s dynamics begin to shift because of Wilson’s success in his endeavors. He becomes a community leader in the prison, and ultimately this changes the entire community’s structure, both physically, as a new “tier” is formed and new therapy groups are organized, and mentally, as the focus of those Wilson comes into contact with begins to shift from short-term to long-term thinking.

In The Master Plan, what is Wilson’s call to action?

Chris Wilson begins to form his Master Plan when he asks himself, “What’s your endgame?” That is, what does he want out of life? What are his goals, aspirations, and dreams? In answering these questions, he can clearly articulate how he wants to define his life and give it meaning. Then, he creates a Master Plan to help him get to his goal.

Wilson’s call to action to his audience is similar. He ends the book with, “That’s my endgame . . . What’s yours?” He asks his readers to live lives of purpose and beauty by having dreams and goals that will give our lives meaning. Wilson believes having an endgame—a purpose—is the first step toward creating such a life. The next step, of course, is to create a Master Plan to make sure people have the best chance of successfully achieving their goals. But having and knowing one’s own individual endgame is the crucial first step, and Wilson invites readers to take it.