Jeff is just a few days away from getting married to Rebecca. On a Friday, he drives down to Newark to get lunch with Robert, who’s going to be one of his groomsmen. They have a long, drunken lunch, during which they reminisce about Yale. During the lunch, Robert also tells Jeff about his challenges as a schoolteacher. The work is hard, but Robert is looking forward to being able to travel back to Rio. Jeff tells Robert that he’s just sold his first novel, and Robert proudly tells Jeff, “I’ll pick up a copy.”
Robert and Jeff seem to be on roughly equal footing following their graduations, at least in Jeff’s mind: they’ve had some limited successes as well as some notable failures. But notice that, just like before, Robert says very little about what’s going on in his life—he certainly doesn’t mention selling drugs or being threatened at gunpoint.
Both Robert and Ty are groomsmen at Jeff’s wedding. The former roommates have a great time drinking and dancing. At the end of the night, Robert thanks Jeff and says good night. That's the last time Jeff ever sees his old friend.
The last time Jeff sees Robert alive, he has no idea that Robert has been selling drugs or experiencing serious difficulties. As far as Jeff knows, they’re both in similar post-Yale situations.
One night, Robert, Victor, and Big Steve, Victor’s older brother, are discussing Robert’s decision to deal drugs. Big Steve says that Robert doesn’t need to sell drugs, but Robert calmly replies, “doing what I gotta do.” Oswaldo, who’s beginning medical school, tells Robert, “Get the fuck out of Newark.” Robert doesn’t listen.
Again and again, Robert’s friends tell him to get away from his neighborhood, which is clearly a bad influence on him. The problem is that, while Robert knows that they’re right, he still loves Newark. His family and his oldest friends live there, and Robert seems to feel a responsibility to live near them—or else he’s afraid to leave his comfort zone again.
Why doesn’t Robert just leave Newark? Hobbs asks. To begin with, he’s loyal to his family. Furthermore, he likes being around his old friends, to whom he’s extremely loyal, and who are very loyal to him. Robert is very generous with his time and money, even though he’s barely getting by himself. In his own way, Oswaldo later says, Robert is “fronting,” pretending to be tougher and more capable than he really is. Around this time, Robert learns that Skeet has brain cancer.
Robert genuinely likes being around his friends and family. But he also likes having a group of friends who idolize him and depend up him for leadership and financial support. Robert’s “fronting,” previously the source of his success as an athlete, a leader, and a student, is now becoming an obstacle to success—it’s influencing him to do the same thing, year after year.
Meanwhile, Raquel Diaz is living in New York while her soon-to-be husband is in medical school. Robert visits her all the time, usually bringing weed. He also visits Rio a few more times, thanks to a cousin who works for an airline. Robert tells Raquel that he wants to live in Rio part-time. Raquel tells him, “You went to Yale. If you can’t figure out how to do what you want to do, that’s your own damn fault.” Robert admits she’s right.
Raquel is yet another close friend who calls out Robert for his complacency: if he really wanted to achieve his ambitions, he could do so with some focus and work. The reality is that Robert doesn’t know what he wants to do with himself.
In his spare-time, Robert works on a new appeal for his father, this time on medical grounds. He writes letters to prison officials, emphasizing his father’s good behavior and begging that he be allowed to leave jail. But because New Jersey prisons are tightening security at this time, Robert’s requests are denied.
Robert continues to fight on his father’s behalf, knowing that his father doesn't have much longer to live. Robert’s relationship with Skeet has always been complicated, and now he seems desperate not to lose his father yet again.
Friar Leahy senses that something is wrong in Robert’s life. But, just as he’s always done, Robert conceals his emotions. He works intensely with his students and athletes and refuses to open up to Leahy.
Even though he’s surrounded by people who love him and care about him, Robert refuses to open up to them—and as a result, he becomes angrier and more frustrated.
Robert finds it hard to deal drugs in Newark, because it’s hard to find good marijuana. Robert begins to grow his own mixed strain of marijuana, growing the plants in his basement and treating them with butane—a task that consumes much of his time. Robert’s friends ask him why he’s still dealing drugs—surely he could find a better job somewhere else. Robert never gives them a straight answer.
The reason Robert doesn’t answer his friends is because he doesn’t have a good answer. He likes being in Newark because he likes being around his friends and being “the man,” and because he’s loyal to his father. But as for why he’s still dealing and taking so many unnecessary risks, he doesn’t even seem to know himself.
Robert spends a lot of time visiting Skeet in prison. It becomes clear to him that Skeet doesn’t have much longer to live. In August 2006, Robert learns that his latest appeal has been denied: Skeet will be kept in prison, in spite of his medical history and the circumstances of his conviction. Later that month, Skeet dies of respiratory failure. The funeral is simple. Robert tells Victor, “I lost my father three times. First when he went to jail. Second when he went back to jail. And now he’s in the ground.”
Robert’s words to Victor sum up the immensity of the pain that he’s been dealing with for all these years. Robert has had to go through all the sadness of being separated from his father—but also the uncertainty and anxiety of having to fight for his father’s freedom. This struggle has left its mark on Robert’s character: it’s made him strong and patient, but also angry and deeply conflicted.
As the 2006-2007 school year begins at St. Benedict’s, Robert begins to plan a career in real estate. He thinks that he can make money by “flipping homes,” and cockily believes he’ll be able to pass the real estate exam. To his amazement, he fails the test the first two times that he takes it. On his third attempt, in 2007, he passes. Robert tells his friends that he intends to get into real estate, continue teaching, make enough money to support Jackie, and go to graduate school. Yet Robert’s friends—as well as Friar Leahy—notice that he seems burnt out.
Robert’s plans for supporting himself become increasingly over-confident and poorly thought-out. He doesn’t seem to be putting the same energy and intelligence into his plans as before—perhaps explaining why he seems burnt out. Notably, this is also seemingly the first time he can’t breeze through a test using only his natural brilliance. Robert keeps coming up against more and more obstacles in the “real” world.
One night, Robert is growing marijuana in his basement when he gets word from Tavarus that Boobie, a member of the Double II Set gang, has a beef with Robert. Robert has been selling his product to Boobie’s usual customers. Later Boobie’s car is parked outside Robert’s house. Robert chooses to go outside and greet Boobie. They sit in the car, and before long, the two of them are laughing.
Robert’s charisma, intelligence, and quick humor make him a surprisingly effective drug dealer, one who’s capable of resolving conflicts with other gangs. Here, it’s suggested, Robert befriends Boobie and smoothes out any difficulties between them.
The following spring will be Robert’s last at St. Benedict’s. He’s informed Friar Leahy that he’ll be taking time to travel and then applying to graduate school. At the end of the school year, Robert attends the senior banquet, where he sees Charles Cawley. Though Robert has seen Cawley from time to time since returning to St. Benedict’s, the meetings are usually awkward. Cawley greets Robert and says he’s sorry—Leahy has told him about Robert’s father. Robert tells Cawley that he’s thinking of applying to graduate schools, but doesn’t specify which ones. As Robert speaks, Cawley notices anger in Robert’s eyes. Cawley, a financier, thinks of Robert as a “poor investment.” He’s invested six figures in Robert’s future, but Robert hasn’t realized his potential.
By accepting Cawley’s money, Robert accepted a certain unspoken obligation to Cawley: he effectively promised to use his Yale education to succeed. Now, Robert is very aware that he’s not making the best use of his degree, and this contributes to the awkwardness of his interaction with Cawley. On the other hand, Cawley’s behavior seems remarkably callous and tone-deaf. To think of a student as an “investment,” good or bad, is dehumanizing and insulting. Like the businessman he is, Cawley expects immediate results, and for this reason he can’t understand what Robert is going through.
Robert never applies to a single graduate school. Instead, he focuses his attention on real estate. But he comes to realize that it’s not a good time to get into real estate in Newark, so he’s going to need another job. A few weeks after the senior banquet, he begins a job at Newark International Airport.
Robert knows he’s capable of doing great things, but instead he takes easy jobs that don’t even require a college degree. Of course, Robert’s apathy is partly the result of his confused and conflicted place in his community and the world in general.