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Content Warning: This section of the guide includes discussion of substance use.
In 1994, Rob and Victor joined St. Benedict’s, which was managed by headmaster Friar Leahy. The school’s motto was “WHATEVER HURTS MY BROTHER HURTS ME” (77). The pupils were largely from lower and lower-middle-class families. Given a choice of texts for a reading assignment, Rob chose Chesapeake by James Michener. He soon became known to the other pupils as the boy who knew the lyrics to every Bone Thugs-n-Harmony song. When Rob’s name appeared among the students with the top three GPAs, his classmates assumed that he came from a relatively privileged background and that his streetwise demeanor was an act.
After school, Rob rushed home to play football with his neighborhood friends. He was devastated when he could no longer play due to not being registered in the state school system. After learning how to swim, Rob joined St. Benedict’s water polo team and made four lifelong friends: Tavarus Hester, Drew Jemison, Flowy Starkes, and Curtis Gamble. Flowy came from the most disadvantaged background and lived with his mother, who had a mental health condition, in one of Newark’s most notoriously dangerous areas. In contrast, Curtis Gamble, whose parents were teachers, had an enviably stable home. The group of friends called themselves the Burger Boyz, as they often went to Burger King between school and practice. Rob rarely ordered food, sucking on ketchup packets instead.
When Rob noticed Tavarus’s poor grades, he suggested that the Burger Boyz form a weekly study group. They congregated in the basement of 34 Smith Street, the Gamble family’s comfortable home. Mrs. Gamble fed the boys hearty meals, while her husband often spoke about how the boys would go to college, as if this was a given.
Due to Tavarus’s troubled background, he was chosen to attend a retreat at the estate of Charles Cawley, a wealthy banker who was also an alumnus and benefactor of St. Benedict’s. Tavarus called Rob after starting a fight at the retreat when another boy remarked on his shoes. Rob told Tavarus to forget about the fight, enjoy the luxury of the retreat, and “think about the big picture” (90). Tavarus returned inspired and determined to go to college. He asked Rob to coach him on studying effectively.
Most weekends, the water polo team traveled to tournaments and stayed at motels. Rob introduced his friends to brandy and smoking marijuana. Afterward, schoolmates asked him if he could supply them with cannabis. Rob referred them to Tavarus, whose brother could acquire drugs. Grateful for the money, Tavarus gave Rob a $20 “kickback.” At the end of his second year in high school, Rob was chosen to lead the freshmen on an Appalachian Trail camping trip. When their campsite flooded during a thunderstorm, Rob led the pupils down the mountain to safety. A school guidance counselor advised Rob to apply to a range of colleges, including Ivy League schools.
Coach Ridley took Rob aside to discuss his marijuana use, pointing out that the habit could endanger his health and future academic prospects. The coach was shocked by Rob’s fury as he accused him of trying to replace his father. Coach Ridley never raised the issue again.
In his senior year, Rob was elected president of the school. He introduced a new regulation prohibiting boots from the school uniform. The decision was controversial as many boys wore construction boots with untied laces, just as Rob had at Mount Carmel. That year, Rob spent much of his time with Curtis after his father died of cancer. He also helped Skeet prepare for his legal appeal. During the summer, Rob and Tavarus interned at a real estate firm. As the law library was close to the Office of Public Records, Rob researched the legalities of murder cases during his lunch breaks. In December 1997, he and Skeet filed an appeal arguing that Skeet’s right to a speedy trial had been violated. The judge upheld the appeal, and Skeet was released from jail. However, he was warned that if the State challenged the decision, he must return to prison until the case was resolved.
Rob’s delight quickly faded as his father’s release did not live up to his expectations. Staying at Chestnut Street, Skeet refused to leave the house and grilled Rob over everything he did. In January, Skeet returned to prison when the State counter-appealed.
Rob was offered spots at Montclair State, John Hopkins, and Yale. As Montclair was the only college to offer him a full merit scholarship, he decided to accept, determined not to place further financial pressure on Jackie. At the St. Benedict’s senior banquet, Rob gave the keynote address, and Friar Leahy publicly praised Rob’s work ethic and achievements. Afterward, Rob was approached by Charles Cawley, who offered to pay his college tuition regardless of where he went. Rob wanted to attend John Hopkins because he felt the college was less elitist than Ivy League schools. However, when Jackie’s supervisor forced her to stay late, she missed the postal deadline to accept Rob’s place. Consequently, Rob accepted his second choice, Yale.
The Burger Boyz spent their last summer together. Each was going to a different college, except for Flowy, who was not able to secure a scholarship. They excitedly looked forward to their future successes, anticipating getting good jobs, investing in property, and raising families. In August, Rob received a letter from his future Yale roommate, Jeff Hobbs. Hobbs revealed he was majoring in English and said he ran hurdles. When they talked on the phone, Hobbs realized that Rob was Black. However, when Rob revealed that he played water polo, Hobbs assumed he was from a privileged background.
Rob’s years at St. Benedict’s illustrate the themes of The Impact of Environment and Upbringing on Personal Outcomes. The school’s headmaster, Friar Leahy, understands that his pupils’ learning obstacles are rooted in their unstable home lives and the poverty of the neighborhood. By instilling them with an affiliation to a new set of values, the school aims to “free their cognition—and their potential—in full” (82). St. Benedict’s provides an environment that counteracts students’ ingrained negative attitudes toward education and aspiration, allowing Rob and the other boys to thrive and feel excited about their futures.
These chapters also delve into The Benefits and Costs of Family and Community Loyalty. St. Benedict’s motto—“Whatever Hurts my Brother Hurts Me” (77) —underlines solidarity and compassion as core life values. This concept is echoed in the close bond Rob develops with the Burger Boyz, “the four friends who would compose the daily heart and rhythm of his life until its end” (86). All four of these boys, except for Curtis, had absent fathers and bonded over this. Their regular meeting place, Curtis’s house at 34 Smith Street, comes to represent their increasing determination to rise above their circumstances as they study together under Rob’s guidance. Hobbs again emphasizes the impact of environment on personal outcomes as the Gamble family’s stable home nourishes the Burger Boyz physically (through Mrs. Gamble’s home-cooked food) and mentally. Consequently, they begin focusing on college and beyond, harboring “little doubt that this future, this collective trajectory, would be earned and actualized” (119). While Rob’s friendships strengthen him, these chapters represent his family loyalty as a burden. He tasks himself with the onerous responsibility of freeing his father from jail, but after Rob succeeds, he discovers that the reality of who Skeet is does not match his idealized notion of his father.
This section of the memoir charts the development of Rob’s character. The memoir once again highlights his conflicted identity when he starts at St. Benedict’s and makes an impression on his schoolmates for two reasons: He voluntarily chooses the 800-page tome Chesapeake for his reading project and also possesses an encyclopedic knowledge of rap lyrics. This dichotomy underlines his dual identity as a “nerd” and a hip, street-smart young man.
Gradually, Rob’s dedication to education and its advantages takes precedence over his allegiance to his neighborhood. This shift is partly prompted by serendipity, as Rob’s prohibition from playing football on a technicality forces him to commit more fully to St. Benedict’s by joining the water polo team. His ambitions and motivation at this life stage are encapsulated in “the one pair of school shoes he shined obsessively, the earnings figures still recorded in the composition book beside his bed, the encyclopedias he kept dusted” (98). Each of these items represents his focus on future success. The symbolism of clothing also emerges in Rob’s controversial decision after he is elected school president to ban students from wearing construction boots with untied laces. His decision seems hypocritical, given that this was the footwear he wore at Mount Carmel. However, the rule recognizes that the boots represent a rebellion against authority, meaning that the boys who choose to wear them are not fully immersed in St. Benedict’s ethos.
Rob is at the peak of his promise at St. Benedict’s. In addition to becoming a top scholar, his leadership qualities emerge, as demonstrated when he leads a group of freshmen to safety off a mountain on the Appalachian Trail. His acceptance into Yale marks the natural culmination of his extraordinary achievements. Nevertheless, Rob shows another side to his character when he responds furiously to Coach Ridley’s assertion that his regular marijuana use will adversely impact his future. Further, although Rob does not sell marijuana to classmates, he receives a “kickback” from passing the business on to Tavarus. These incidents foreshadow Rob’s repeated reversion to marijuana dealing in later life.
These chapters also foreshadow the author’s friendship with Rob at Yale, describing how Rob receives a letter from him. From this point, the narrative shifts to Hobbs’s perspective as he admits to his youthful naivete about the gap between his own privileged circumstances and those of Rob. Utilizing self-deprecating humor, the author underlines his lack of knowledge about social deprivation, asserting, “As far as I knew, all of northern New Jersey was affluent” (119).
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