Pineapple Street

“The Stocktons may have let her marry their son, but she understood on a bone-deep level that they would rather let her walk in on them in the middle of an aerobic threesome with Tilda’s bridge partner than have her studying their tax returns.”

This quote exemplifies Jackson’s use of wry humor to satirize the secretive, elitist mindset of the extremely wealthy, and it also adds a tone of lightheartedness to the author’s social critique of the issues surrounding inherited wealth. In this elusive—and exclusive—world, suffering a scandal is preferable to revealing the details of their wealth. This attitude emphasizes the central role that money itself plays in their daily lives and unspoken social rules, and it also solidifies their unspoken exclusion of Sasha. She is not considered part of the family because she is not trusted with detailed knowledge of her new family’s money (and, by extension, of her own financial future).

“Sasha must have watched The Wolf of Wall Street too many times, because she always thought rich New York guys would have slicked-back hair and constantly be paying for bottle service at clubs. Instead, they apparently wore sweaters until they had holes in the elbows and had unhealthily close relationships with their mothers.”

In this quote, Jackson alludes to the 2013 film The Wolf of Wall Street, which was directed by Martin Scorsese. In this film, a stockbroker named Jordan Belfort starts his own firm and illegally accumulates millions of dollars. He parties hard and shows off his wealth, and thus his character strikes a sharp contrast with that of Cord, whose modest demeanor defies this stereotypical image of extravagant wealth. This is an important characterization because it shows that Cord doesn’t care about materialistic things. It also highlights a distinction between “new money” and “old money.” Unlike Jordan Belfort, Cord has grown up with money and with people who are accustomed to having access to immense inherited wealth. Jordan Belfort, on the other hand, worked and conned his way into his money, so he shows off his wealth because he is proud of how much he himself has managed to amass.

“She felt lonely and pathetic, but she knew that all across the city there were girls just like her who had spent their Saturday nights waiting for something to happen, nursing a drink or reading a paperback in a coffee shop or scrolling endlessly on their phones, alone and biding their time until their real life would begin.”

In this quote, Georgiana is portrayed as a relatable young single woman living in New York City. Like many young women in this category, Georgiana wants to experience a true romance, but she is instead often left disappointed by nights that become uneventful. In a city that offers so much scope for social adventure, there is an implied promise of excitement, especially given Georgiana’s wealth and means. However, what Georgiana lacks is the strength of will to make things happen for herself, and the act of waiting for exciting things to happen can leave people unsatisfied.

“Playing tennis was and always had been the cleanest line of communication between Georgiana and her mother. Tilda was hard for her to talk to; she was of a generation that despised difficult conversations, and shut down at the slightest hint of conflict or unpleasantness.”

This quote characterizes Georgiana and Tilda’s relationship as close but not intimate because they have a difficult time talking about real things and real problems, even though they spend so much time together. Because they limit themselves to shallow, “safe” interactions, their physical proximity and time spent together have not allowed them to build up a friendship based on candid, genuine connections, and Tilda is not Georgiana’s confidant. This dynamic foreshadows the conflicts that Georgiana will experience in silence throughout the novel, for despite her many material comforts and benefits, the stilted nature of the Stockton family’s interactions imprison her within a world in which it is better to be polite than to be genuine.

“When they decided to get married, Darley couldn’t ask Malcolm to sign a prenup. The entire thing felt like arranging for their eventual divorce and drew a thick line between what was hers and what was his. She didn’t feel the money belonged to her anyway. It belonged to her grandparents and her great-grandparents. She had done nothing but act as a drain—private school and vacations and clothing and death by the thousand cuts that was raising a child in the most expensive city in America.”

This quote reveals that Darley’s true priorities are love and the integrity of her marriage, not the legacy of the Stocktons or the social status that comes with having access to unimaginable amounts of wealth. Her actions also establish that not everyone who is so wealthy is preoccupied with money alone. Instead, Darley has the strength and integrity to question the nature of her own extreme privilege and make important decisions based on matters of the heart, resisting the seductive bubble of financial privilege. Darley is not threatened by outsiders, and she considers her husband to be more important to her happiness than the status quo of the wealthy New Yorkers she grew up with.

“Mullin had irrevocably changed something between her and her brothers, but also in how she thought about love. She had seen what all-consuming passion looked like, how it felt to ride the currents of intense adoration and fury, and she didn’t want it. She wanted someone stable, someone easy, someone who loved her but not enough to lose himself entirely.”

Sasha’s origin story is crucial to her characterization. All-consuming love is frightening to her, and she appreciates Cord’s decorum and the independence she enjoys within their relationship of mutual affection and respect. This dynamic implies that she’s genuinely uninterested in the financial value that Cord brings to her life, for her own work ethic and strong track record of providing for herself prove that she has no need to engage in the “gold-digging” activities her in-laws suspect. However, this slightly detached approach to love also implies that Sasha has a difficult time accepting and embracing her relationship completely, which helps explain why she feels so out of place within Cord’s tight-knit family.

“When she was running, she never worried about who was looking at her or what she should say; the butterflies and knots in her stomach were replaced by the pleasant burn in her lungs and her legs, knowing that the only thing she needed to worry about was moving, pushing forward, that she belonged entirely to that moment.”

This quote reveals that Georgiana experiences social anxiety. The downside of growing up in a bubble of privilege is that she has internalized how closely people watch and judge one another. Close-knit communities are also prone to gossip. Georgiana feels most empowered in her body when she is running because the rest of the world melts away and she can be herself without worrying about how she looks. This is an important new layer to Georgiana’s inner needs and desires that adds nuance to her character.

“How much of Malcolm’s ousting was because he was in the wrong place at the wrong time, and how much was because he wasn’t an old boy with a last name like Dimon, Moynihan, or Sloan? Body said, ‘We’re firing you because you don’t have a white dad to stick up for you,’ but to Darley it was clear as day.”

Here, Darley notes the implicit bias and racism in her community of wealthy, white, influential people. No matter how hard Malcolm works or how good he is at his job, he’ll always be considered an outsider simply because of his background and heritage. Because of her marriage, Darley is now directly impacted by the racist structures and nepotism that have always influenced her community, and of which she was previously unaware. She keenly realizes how differently Malcolm would be treated if he had a wealthy white father. This quote exposes the injustice inherent in the world of the extremely wealthy and establishes how people like Malcolm are left out of privileged spaces in spite of their merits.

“Every society had traditions, institutional knowledge, their own innate sense of how things should be done…At the bar, a coaster on top of a pint glass meant the seat was taken and the drink was still good. These rules were so deeply ingrained in Sasha that she barely had to think twice about them, but suddenly, with Cord, she was subject to an entirely different array of social niceties.”

Jackson’s novel is, in part, a sociological study of the different class-based cultures that coexist awkwardly within American society. Sasha is from a different culture than Cord and the other Stocktons, and such stark differences in the approach to work and wealth can lead to misunderstanding and conflict. However, if such stark differences are understood in terms of differing cultures, then the implication is that there is a way to gain mutual understanding despite those differences. Cultural differences can be learned, understood, and interrogated, which can lead to more empathy and inclusion. At the same time, Jackson notes how difficult it is to learn the nuances of an unfamiliar culture.

“The weird thing was, though, Sasha wouldn’t have traded places with them. She loved working at the garden store…and even when it sucked, it had taught her how to work. Sasha wanted to be successful, and she understood that if she wanted to do anything of significance it was on her to make it happen.”

In this quote, Jackson characterizes Sasha as being proud of her upbringing and tenacity. Sasha appreciates the value of a strong work ethic, and contrary to Georgiana’s opinion of her, is not interested in taking advantage of Cord’s vast resources. Instead, Sasha knows that her own self-worth comes from working hard for her goals and making her life what she wants it to be rather than relying on other people to help her get ahead. Sasha is like Malcolm in this way.

“It was easy to say that money was the root of all evil, but so many of the things money could buy provided dignity, health, and knowledge.”

Georgiana tries to reckon with the realities that come with her extreme privilege. She is defensive over her privileged upbringing and circle of friends because she doesn’t believe that having wealth automatically makes someone a “bad” person. Georgiana sees both the good and the bad qualities in the possession of wealth. Wealth can deteriorate one’s morals, but it can also build communities and knowledge. When put to good use, wealth can be powerful in changing the world for the better, and ultimately Georgiana’s struggle is in finding a legitimate way to use her own wealth to improve the world around her rather than to indulge shallow whims.

“She had been a child, a stupid child, but Brady had seen her. Her love for him had filled her with shame, but also with a power that burned hot and bright. And now he was gone, and she would never feel that power again.”

This quote expresses an important nuance of Georgiana’s characterization. Brady’s death is, for Georgiana, the death of her first attempts to achieve personal empowerment. Despite her privileges, Georgiana has never before experienced true empowerment because her life is so cleanly cut and metaphorically bubble-wrapped for her. Brady was a person she truly wanted, and their relationship, though an affair, was a joyous secret. In this quote, Jackson emphasizes that shame and empowerment are not paradoxical, that one can lead to the other, and vice versa. Georgiana feels defeated by Brady’s death in part because she sees it as the death of what was a burgeoning sense of freedom and identity.

“Inheritance had a way of ruining people. Obviously being born into poverty was incomparably worse, but since both Darley’s mother and father had come from great wealth, she had scads of first and second cousins who demonstrated just how badly money could fuck you up. She had cousins who had gone into law, politics, and medicine, sure, but she also had cousins who did absolutely nothing.”

The question of inheritance and its impact on the individual is a key source of conflict in this novel. In this quote, Jackson uses Darley’s perspective to highlight that some people can use their inheritance for good, but also that being born into enormous wealth can hinder people from being active at all. People can waste lives and privilege away by doing nothing because they have the money to fund a lifestyle of nothingness. For Darley, and Jackson, this is a lifestyle of emptiness and is a reason why inherited wealth is not a good thing.

“But it was now clear to Sasha that they had only confided their secrets in her because of how little it mattered to them what Sasha thought. She wasn’t really their family; she wasn’t someone who could pass any kind of meaningful judgment. She was a receptacle for an emotional outburst, the human equivalent of screaming into a pillow.”

Sasha’s status as an outsider has a strong influence on the problematic dynamics between her and the Stocktons. Though both Darley and Georgiana confide secrets to Sasha, Sasha believes that they do so not out of sincere trust or an honest desire to develop a friendship. Instead, they confide in her because she is an outsider, so her opinion doesn’t matter. Darley and Georgiana cannot feel judged by someone whose thoughts do not matter, after all. This quote reminds the reader that what had been burgeoning friendships between Darley, Georgiana, and Sasha were one-sided; they confided in Sasha but no one in the Stockton family besides Cord seems interested in Sasha’s life.

“She felt she had seen something the Stocktons wouldn’t have liked her to see. They were all so private. They were secretive. They were desperate to keep up appearances and make sure no cracks showed in their façade. Well, Sasha had seen the cracks and now they hated her for it.”

As an outsider to the world of elite class that the Stocktons represent, Sasha’s knowledge of their intimate affairs presents a potential threat. Her access to their private problems thus intensifies their perception of those problems. This unspoken dynamic emphasizes how difficult it is for Sasha to be considered a part of the family. Intimacy is difficult to build because intimacy requires openness and vulnerability. Culturally, the mega-rich Stocktons want to protect their image and keep their surface appearance as perfectly manicured as the rest of their aesthetic. It is easy for them to blame Sasha for Georgiana’s mental health crisis because they see Georgiana as too vulnerable and Sasha as too much of an outsider to understand Georgiana’s vulnerability.

“Georgiana was tired of herself. She was tired of being drunk and hungover. She was tired of dressing up for parties. She was tired of tennis at private clubs…She was tired of Berta cooking her meals and mopping her floor. She was tired of clicking away in the smallest room…pretending to be doing something—anything—that mattered when, in her entire life outside her job, she was yet another cog in the machine that kept everything moving away from fairness and justice and humanity. She couldn’t do it anymore. She couldn’t be this person. She needed to change.”

This quote captures a major shift in Georgiana’s characterization. Georgiana is the character who changes the most throughout the course of the novel. Here, Jackson reveals the moment in which Georgiana reckons with her privilege and her wasting of that privilege in partying, laziness, and meaningless pursuits. Georgiana’s criticisms of her own life, and her ownership of responsibility in the meaninglessness of it, is an important first step in changing into a better, more conscientious, and happier person. This quote also emphasizes that money does not buy happiness.

“What if, what if, what if? There were countless things that could go awry, and money was the best way to shore yourself up against tragedy.”

Darley sees Georgiana’s decision to divest herself of her fortune as a mistake. Darley has let go of access to her own trust fund, but she has kept it secure for her children. Darley has learned the hard way that large stores of money are useful in protecting oneself against the unpredictability of life. Malcolm’s unexpected firing has taught Darley that money is valuable as a safety net. This is an important point because while money can’t necessarily buy happiness, it can buy security. Georgiana is young, unmarried, and childless, so she doesn’t need to think about her financial responsibility to others. The issue at stake here is that Georgiana has more money than she would ever need to use as long as she lives responsibly, while her unlimited access to money has paradoxically limited her from achieving her full potential.

“She had been the Georgiana of her family the whole time, throwing elbows at Mullin because he didn’t belong. But there was one crucial difference: Her brothers had let her know she was wrong…Had Cord done the same? No. He had somehow managed to play both sides, never calling out his sisters, never truly promising to pick Sasha and put his wife first. It hurt. Sasha knew that when she had fallen in love with Cord she had said she wanted someone who loved her but didn’t need her. But maybe she had been wrong. Maybe, when it came to marriage, she actually needed Cord to need her too.”

Sasha reflects on her own role in her family in order to better understand the Stocktons. Sasha has also treated someone like an outsider in her family, but her family holds her responsible for her behavior. This is an important difference because part of Georgiana’s problem is that her childishness is enabled by her family. Relationships change and needs in those relationships change; for Sasha, what used to please her (the rational side of Cord) has turned into a problem for her relationship. Sasha learns from her own family and her own experience with Mullin that treating someone like an outsider only causes damage to the interpersonal relationships involved. Furthermore, this moment is important to the development of Sasha and Cord’s relationship. For their relationship to work, Cord must be more confrontational with his family, which is a large risk but a necessary one in order for both Cord and Sasha to grow.

“It’s uncomfortable to talk about class, I know you get all awkward and WASPy whenever it comes up. And it’s most uncomfortable for the really rich and the really poor. But you and I are from two different classes. And that’s weird. When you marry outside your class it’s somehow too difficult to even discuss. We just ignored it.”

Sasha finally confronts and acknowledges a taboo issue in both her marriage and in America at large. Marrying between classes is like marrying between cultures; there are learning curves and compromises that must be negotiated in order to ensure success. Class is an especially taboo topic in America because the capitalist system creates a world populated by both the mega-wealthy and the destitute. Those at the top, like Cord and his family, are uncomfortable being reminded of their immense privilege in the context of an unforgiving capitalist system. Cord doesn’t want to be judged for his money or his family lineage, but his inability to be vulnerable about the class issue prevents him from developing a more meaningful relationship with Sasha and helping facilitate a better relationship between Sasha and the rest of his family.

“Georgiana was starting to see that her relationship with money was all intertwined in how she thought about friends and marriage. Unbeknownst to her, she had been trained her entire life to protect her wealth…Intertwined with this doctrine was the fact that marrying outside their class would dilute their wealth. It was best for the rich to marry the rich. Georgiana hadn’t ever realized how deeply ingrained this belief was in her psyche.”

Another important revelation Georgiana has that leads to her character development is the discovery that she refused to see for a long time: Her understanding of the world is inevitably distorted by her own extremely privileged relationship with money. Subconsciously, she has grown up with the assumption that the Stockton family fortune is so important that it must be upheld at all costs, even if that means ostracizing people or rejecting certain life experiences. By finding fault in the very structure of wealth management and wealthy families, Georgiana can genuinely separate herself from her money as a way of separating herself from a snobbish and borderline paranoid attitude about the less wealthy.

“Or if over time she might consider the fact that he was older than her, more powerful than her, as evidence that he might not have treated her fairly. For now, she just hoped that Amina was okay, she hoped that she had found peace. Georgiana knew that their paths might cross again someday, working side by side toward the same common good, and she liked to think that would make Brady happy. That his legacy on this earth, however complicated, had doubled in his absence, the two halves of his heart joined in the same pursuit, that all the love he had shown Georgiana might radiate out into something truly good.”

In this quote, Georgiana continues her character development by rethinking her relationship with Brady. She steps away from grief and resentment and into acceptance and compassion. First, there’s the compassion she extends to herself because her relationship with Brady was possibly a problematic relationship in which Brady took advantage of her youth, inexperience, role at work, and obvious infatuation with him. Secondly, she extends compassion to Brady’s wife Amina, demonstrating that Georgiana has started thinking of people other than herself. Lastly, Georgiana decides to find closure on her relationship with Brady as well as with his death by looking to the future and projecting her newfound compassion into work that would do good things for communities, thereby honoring Brady’s memory.

“But her biggest mistake had been giving money so much power over her life. By keeping Malcolm’s secret, she was buying into the idea that her world was a club only available to those with a seven-figure income. And she didn’t want to live that way. She wanted, for the first time in her life, to peel back her bitter rind and open up to the sweetness within.”

Darley also has her own reckoning with money, which also provides character development. Darley has been cautious about money, even in rejecting her inheritance for Malcolm. She has internalized the danger of having money, namely that many people will try to take advantage of her. She has therefore kept her social circle small and does not challenge herself to exist outside of the bubble she grew up in. Malcolm’s family is the only exception to this, but they spent years getting to know one another and building trust. Furthermore, Malcolm has proven to be excellent at fitting into Darley’s family and exclusive world, making it unnecessary for her to undergo much of an evolution herself. Thus, Darley unwittingly perpetuates the cycles and structures of snobbery and exclusivity. By acknowledging this reality, Darley can grow like Georgiana and become a more open and empathetic person.

“‘Mom, I think poverty is a really important dinnertime conversation,’ Georgiana countered. ‘I think that’s a big mistake we’ve been making as a family, only talking about things that make us comfortable. We need to talk about what life is actually like for most people.’”

Georgiana’s character development serves as a catalyst for greater change within the Stockton family. By seeking a more genuine lifestyle and opening herself up to uncomfortable topics of discussion, she influences her family to become more vulnerable to discomfort. Georgiana has learned that being uncomfortable is an important way of understanding how to live in the real world. This quote demonstrates that Georgiana has fundamentally changed, and also that she will lead her family into having more meaningful interactions with and conversations about the world around them. Georgiana breaks the Stockton family cycle of taboo conversations.