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Content Warning: This section of the guide includes discussion of racism.
Jackson recalls introducing Patrick to her family for the first time. While Ketanji’s parents could see that Patrick was a good person who cared about Ketanji, they were also concerned that they would face discrimination as a mixed-race couple. Jackson was hurt that her parents thought that Patrick might leave her if they experienced such challenges and was frustrated by their doubts, but she tried to gently reassure them. Jackson knew that Patrick had a very different upbringing from her own as the son of an upper-class family from Cape Cod, but she felt welcomed by his warm and hardworking parents. More difficult to overcome were Jackson’s own insecurities about her looks and lovability, which had rooted themselves in her mind after her experiences in high school. The two were also on demanding career paths, as Patrick was beginning medical school at Columbia University and Jackson was completing her degree at Harvard. With so much uncertainty, Jackson felt nervous about their relationship’s future.
Jackson recalls a devastating childhood experience in which a little white boy she had befriended told her that he was not allowed to be friends with her and that they could not play together anymore. She had to remind herself that just because she experienced such rejection in the past did not mean that her relationship with Patrick would turn out the same way. Jackson’s friends were also protective of her, and they even questioned Patrick about his intentions with her without her knowing. When they realized that he was genuinely interested in committing to Jackson, and aware of how some might perceive their relationship, her friends became supportive of their romance. Jackson concludes the chapter by reflecting on how Patrick’s ancestors and her own experienced completely different aspects of the American experience. To her, that makes their relationship feel miraculous.
Being the descendent of enslaved people, Jackson can only reliably trace her exact ancestry to Civil War-era documentation. By contrast, her partner, Patrick, has detailed information on his ancestors, many of whom were the descendants of Puritan immigrants and among the most privileged and powerful people in America. Jackson considers how her husband became such an intelligent and compassionate person. She credits his parents’ and grandparents’ influence for helping him develop into an open-minded person with a heart for justice. For instance, his lawyer grandfather “Pappy” had befriended his Black colleague Wiliam Thaddeus Coleman, Jr., a prominent lawyer who worked on groundbreaking civil rights cases. Pappy taught Jackson to be sensitive to other people’s experiences and work against discrimination.
As Jackson completed her internship at Harlem’s Neighborhood Defender Service, she realized how being charged with a crime could easily plunge people’s lives into chaos long before the verdict. Living and working in New York made Jackson realize how her upbringing and education had sheltered her from witnessing the realities of inner-city poverty, and she was disturbed by the conditions she saw so many residents contending with. When accused of a crime, many people were coerced into pleading guilty to avoid the risk of a possibly disastrous trial by jury and even more punitive sentencing. Jackson channeled her new knowledge into her thesis, “The Hand of Oppression: Plea Bargaining Processes and the Coercion of Criminal Defendants” (164).
Jackson recalls her joy at graduating from Harvard knowing that she and her closest friends had all been admitted into Harvard Law School the following year. She was impressed by her classmate Charles E. Roemer’s speech about the life-changing effects of kindness, and she committed herself to this philosophy. Jackson acted on the advice of her writing professor and deferred her enrollment to law school to work at Time magazine for a year as a reporter-researcher. While Jackson’s year as a staff writer did not change her dream of becoming a lawyer, she did enjoy her experience of exploring New York City and living closer to Patrick, who was still studying at Columbia University. After enjoying a European vacation—her first time traveling outside the US—Jackson returned to Boston and began law school.
Jackson found law school as grueling and exhausting as it was reputed to be, and she had to adjust her debating approach to be more combative and less collegial. Knowing that being on the board of the Harvard Law Review would be an asset to her career, Jackson entered the publication’s writing competition and was awarded a spot on the board for her work. On the staff of the Review, Jackson noticed that there was a healthy diversity of opinion among its writers. Her position at the Review was demanding and rewarding, and it became her favorite part of attending law school. The author reflects on how the annual portraits of the Harvard Law Review reflect society’s progress, as they now include women and people of color.
As Jackson focused on law school, Patrick was ready to complete his medical training and applied to 15 hospitals across the northeast and Miami. During his trip to Miami, he asked for Ellery and Johnny Brown’s permission to marry their daughter, and they gave him their blessing. Patrick invited Jackson to his grandmother’s house on the coast of Maine, and he proposed to her in the snowy yard. Jackson was elated to agree.
With Patrick completing his surgical residency at Massachusetts General Hospital and Jackson completing law school at Harvard, the two could finally live together. After graduating in 1996, Jackson was accepted to two clerkships. The first was with Judge Patti Saris, whom Jackson came to respect for her ability to excel at her position while also being a mother to four children. Saris was warm and engaging and brought Jackson into her inner circle, making her clerkship enjoyable.
Jackson traveled to Chicago to attend her friend Denise’s wedding, where she met Barack and Michelle Obama. Jackson sensed at the time that the two were going to accomplish great things, and she was excited when, years later, Obama announced his presidential campaign.
Soon after, it was time for Jackson’s own wedding, and she reflects on how meaningful it was for her and Patrick’s families to participate in the ceremonies and enjoy each other’s company. Jackson felt amazed that she had found her life partner and reflected on the good fortune of meeting him.
Jackson found her clerkship tasks interesting, as they required her to research and understand a variety of cases, from patent suits to constitutionality issues. One memorable case was Guckenberger v. Boston University, in which a law student with a learning disability sued the school for withdrawing accommodations that it had previously promised her. Jackson recalls Judge Saris ruling that the university had to compensate the students it had neglected, and Jackson felt satisfied with that result.
To complete her second clerkship, Jackson moved to a studio in Providence, Rhode Island, so that she could work for Judge Bruce Selya. She was saddened to have to live apart from Patrick, who was living with his parents in Boston as he continued his work at the hospital. Selya was in his sixties and suffering from macular degeneration, so he needed his clerks to live nearby and drive him to court. Jackson describes her new boss as a “brilliant” and “meticulous” man who was renowned for his incredible vocabulary (205).
Jackson faced her own doubts about her career of choice, sometimes wondering if she should have pursued writing or acting instead. Ultimately, she realized that law was the best choice for her, and she committed herself to improving people’s lives through the law. After this lonely year, Jackson was keen to reunite with her husband as he pursued a fellowship in Washington, DC, and she moved there with him to work for the law firm Miller Cassidy. Jackson and her husband luxuriated in finally having Sundays off work for the first time, and Jackson also felt a positive connection to DC, the city of her birth.
Jackson was surprised to receive a phone call from one of her professors encouraging her to apply for a clerkship on the Supreme Court. She excitedly agreed, and Justice Stephen Breyer interviewed her soon after. Jackson was thrilled to accept his job offer—even though it meant a return to a more grueling schedule.
In these chapters, Jackson details stories from her and her husband’s lives that show the importance of Confronting Racism. Though Patrick is white and has never faced racism himself, Jackson credits him and older members of his family with standing up against racism in the world around them. For instance, Jackson shares how her husband’s grandfather Pappy questioned the anti-Black discrimination that was so normalized in his day. Jackson considers Pappy “a progressive before that term was popularly understood” and “a man ahead of his time” because of his belief in equality and his friendship with his Black colleague, lawyer William Thaddeus Coleman, Jr. (157-58). When his young grandson Patrick asked why all the diners at their restaurant were white while all the serving staff were Black, his grandfather encouraged him to think about why that could be. The author praises Pappy for not shying away from such questions but instead planting “the seed of inquiry” into Patrick’s mind and treating the matter seriously (159). In sharing these anecdotes about Pappy, Jackson credits her husband’s family for teaching him empathy and anti-racist values that went on to inform his student activism and relationships.
Jackson emphasizes the importance of these values by sharing a memory from her childhood about a friendship cut short when her white neighbor Tommy was no longer allowed to play with her. She recalls the painful realization that Tommy’s mother’s decision was about her race: “He said that even though he and I were exactly alike, his mother thought I was just too different, and that kids like Tommy shouldn’t spend time with kids like me. Tears sprang from the corners of my eyes as I tried to understand what was happening” (147). By sharing this anecdote, the author shows a personal example of the needless division and emotional scars that racism creates.
The success of her own interracial relationship stands as a counterexample, showing that these divisions need not define people’s lives. By discussing her parents’ doubts about their relationship, Jackson shows how anti-Black racism can create anxiety for interracial couples and their families. She recalls how her parents “expressed their concerns” about how people would treat her and her husband (141), worrying that Patrick would be unable to handle this scrutiny and potential discrimination. Jackson understands her parents’ concerns, but she also remembers how determinedly she reassured them that she and Patrick should be together. She explains, “Could I adequately describe to these two people, who had only ever wanted the best for me, how loved and special Patrick made me feel?” (142). By detailing her family’s doubts, Jackson makes her wedding story all the more joyful, as she and Patrick were “thrilled to the sight of [their] families and friends exuberantly reveling in [their] bond” (195). By celebrating her enduring love story with her husband, Jackson emphasizes how love and mutual respect can prevail over division and discrimination.
Jackson’s early legal career offered ample opportunities for confronting racism. Recounting her experiences working with indigent clients for the Neighborhood Defense League in Harlem, she remembers, “That summer, I understood for the first time the awesome power of the law to help or to hurt real people” (162). Jackson recognized that people who live in poverty in the urban core, especially Black people, are more vulnerable to being wrongly prosecuted. She argues that over-policing poor communities in which people do not have access to social services or legal advice “could lead to a loss of liberty and livelihood, and sometimes even cost poor people their lives” (162). In her work with the Neighborhood Defense League, Jackson did what she could to combat these systemic disparities.
Jackson acknowledges that these harsh realities were different from her own experience, as she had the good fortune to be raised in a middle-class family in a safe area. She describes how her experience working in Harlem helped her grow beyond her “sheltered, middle class existence” (162). Jackson credits this internship experience with motivating her to reconsider the justice system’s impacts, and she returned to her studies “with new and burning questions about the fairness of the criminal justice system as it related to poor people” (163). Jackson grappled with this issue in her thesis, in which she argued that coercive plea deals were an abuse of the justice system’s power. Jackson’s memories and her work as an undergraduate student show that she was motivated to break barriers not only for herself and others like her but also for vulnerable people lacking in knowledge and resources.



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