Pineapple Street

In Pineapple Street, Jackson explores the various consequences of seeking happiness through wealth alone. Despite the immense wealth of the Stockton family, their members still face many internal and external conflicts that are not solved by money and are in fact sometimes caused by it. One of the things that Sasha, Georgiana, and Darley have in common is their various realizations of how profoundly money can complicate one’s pursuit of happiness.

At first, Darley appears to be a character who chooses to value her relationship with her husband over her family’s money. She gives up her rights to her inheritance so that Malcolm doesn’t have to sign the Stockton pre-nuptial agreement, even though he is perfectly willing to do so. This demonstrates that Darley doesn’t see money as the key to happiness and instead chooses love as the source of her happiness. Yet Darley does still value money a bit too much. When she let go of her inheritance, she and Malcolm were both making high salaries, and Darley’s lifestyle didn’t change at all. When Darley gave up her job to be a stay-at-home parent, she relied on Malcolm’s income to uphold their luxurious lifestyle. But when Malcolm is fired from his job, Darley is forced to revisit her relationship with money. She realizes that access to money is access to security. However, Darley’s opulent lifestyle is not a necessity but a perceived birthright. It is true that life is full of unexpected challenges, and money is often necessary to help manage life’s crises. However, this doesn’t mean that money can buy happiness, for it is ultimately a means, not an end in and of itself. Darley also has a fraught relationship with money outside of the needs of her family. She’s had experiences with people whom she thought were friends but were actually using her for her access to money. Darley sees money as a liability even as she understands its significance in building stability. Money complicates Darley’s life, but it doesn’t make her happier.

Upon her entry into upper-class society, Sasha also learns quickly that money cannot buy happiness. Sasha grew up comfortably middle-class and learned the value of a dollar at a young age because she always had a job and saw her parents working hard but prioritizing their family. Sasha is herself an independent and hard worker. Her graphic design company makes her a good deal of money. She doesn’t just support herself before her marriage to Cord; she thrives. She independently affords a nice apartment in New York City, one of the most expensive cities in the world. Cord’s money doesn’t impress Sasha. She can appreciate the stability she can look forward to in marrying a man with money, but his money is not the reason why Sasha likes or loves him. Sasha sees the Stockton family wealth as more of a burden than anything else. She is burdened by the house on Pineapple Street, a major financial asset. She is burdened by the pre-nuptial agreement, which is a way of protecting the Stockton family wealth. She is also burdened by the attitude the mega-wealthy have toward anyone outside of their class: namely, suspicion and disregard.

Sasha is made an outsider because she is of a different class and therefore a different culture. Sasha doesn’t know all of the unspoken rules about being wealthy, and there is a lot about the Stockton family’s conservative dynamics that frustrates her because their inability to have real conversations is tied to their dynastic money. Sasha understands that life is about a lot more than the mere preservation of wealth. Sasha is the character who proves that possessing a large fortune does not necessarily make a person better than others who have less, and thus she is something of an existential threat to the established order of the Stockton family wealth. Sasha doesn’t need or want money from the Stocktons, but she still has to deal with jokes that are little more than accusations of greed. Georgiana and Darley secretly refer to her as the “Gold Digger,” which thinly veils their real concern that Sasha is only interested in Cord for his money. Sasha is constantly forced to prove that she is a good person, a valuable asset in her own right, and unimpressed by the Stockton family’s wealth while simultaneously conforming to their narrow-minded culture, simply because she didn’t grow up with money and they did.

Georgiana also learns that seeking happiness through wealth is no way to live. Georgiana is emotionally devastated by her affair with Brady and his unexpected and tragic death. Not only does money fail to help Georgiana through her heartbreak, but it also makes this conflict worse. Money allows Georgiana to mix alcohol with prescription drugs and escape into a world of privileged partying. Furthermore, her family’s desire to keep her protected from the reality of the world has made her an infantilized adult incapable of dealing with life’s challenges. Thus, Georgiana is actually held back from her full potential because of her access to money. Being wealthy has prevented Georgiana from gaining valuable life experience about the greater world around her. Thus, she defends this bubble of privilege because it’s the only thing she knows. When Georgiana decides to be a better person, she chooses to divest herself of her fortune. Georgiana is confident that the road to happiness and self-fulfillment is unrelated to her possession of money.