Under a Painted Sky

As an enslaved person, little is known about Annamae’s heritage beyond her own lifetime. She does not have a last name in the story, and if she had, it would merely be the last name of her enslaver. She had two brothers, Tommy, the youngest, who died when he was seven, and Isaac, the oldest, who just turned 20. Annamae’s quest in the novel is to liberate herself from enslavement and reunite with her brother at Harps Falls, which is where the climax of the story takes place. Annamae is depicted as insightful and independent from the start of the story. She realizes that Samantha wanted to kill herself in the bathtub. Annamae had already been planning her escape from the slave state of Missouri on a “Moses train” (part of the Underground Railroad) when she meets Samantha. Annamae reminds Samantha several times that, as a female enslaved person, she has spent her entire life trying to protect herself. Although joining forces is beneficial to both, Annamae knows that she benefits additionally for passing as someone whom Sammy is enslaving, since it might protect her from being identified as a runaway. Like Samantha, Annamae has experienced loss and trauma in her short life, much of which is symbolized by her revulsion for onions, which were used to torture and humiliate her enslaved family.

Annamae is buoyed by her unflagging Christian faith in God and is undeterred in her goal to meet up with her brother at Harp Falls. Her goal adds a purpose to the journey, which Lee uses to shape the arc of the novel. Annamae has many practical skills, such as sewing and cooking, which she uses to help earn their place with the cowboys. Like Samantha, she is fond of music, but her knowledge is limited to spirituals or songs of the Underground Railroad. This is in contrast to Samantha’s training as a classical musician. Annamae does, however, possess great storytelling skills, an important literary form in the oral traditions of enslaved people. African cultures, from which Annamae is descended, have strongly developed oral storytelling traditions. These were brought to America by kidnapped African people and became part of early African American literary tradition. Anti-literacy laws enacted in slave states between 1740 and 1834 made it illegal to teach enslaved or free African Americans, reinforcing the importance of orality in the community’s culture (Maddox, Carliss. “Literacy By Any Means Necessary: The History of Anti-Literacy Laws in the U.S.” Oakland Literacy Coalition, 2022). Her stories serve as parables or lessons for the cowboys and Samantha. Annamae’s love interest in the story is the Mexican cowboy, Peety.

West Pepper is one of the three older teenage boys who join with Sammy and Andy to form the remuda (a herd of horses that are saddle-broken) or family. Like his cousin, Cay, and his friend, Peety, West is a cowboy from Texas. While still teenagers themselves, the cowboys are more physically and sexually mature than the younger “boys.” West is described as someone whose “perfect eyebrows and straight nose could have inspired Michelangelo” (54), and West’s physical attractiveness is confirmed by other young women he meets on the Oregon Trail. West is also a “flawed” character, which Lee also expresses physically, seen in his “frowning mouth and the slouch of his lean and muscled frame” (54). He remains aloof with Andy and Sammy for much of their journey together and is the most reluctant to allow the younger teenagers to remain traveling with the cowboys. He is a capable cowboy, excelling in the skills of shooting, roping, and riding, as is seen during the stampede roundup and the “cowboy lesson” days. He is also brave, risking his own safety to rescue Sammy from the burning tree during the animal stampede. Lee uses these qualities to drive both the humorous and the dramatic episodes throughout the novel.

West also has a dark and mysterious side, suggested by his scars. He was abused by his father when he was a child, in part because his father had an alcohol addiction and in part because there was something about West that was different that he could “never change,” no matter how hard he tried (165). Lee makes the true meaning of this “something” ambiguous to Samantha and the reader. At times, Samantha believes that his detachment from her is due to a revulsion at the thought of connecting romantically with someone who is Chinese. At other times, she wonders whether he is gay but does not want to act on it. It turns out that it was his racist prejudice that initially prevented him from admitting his feeling for Samantha.

Cay is the first of the cowboys to be spotted by Samantha. He is described as extremely attractive to women with sandy curls and grass-green eyes. It is because of his womanizing that the young men must flee Texas. He has an outgoing personality in contrast to his introverted cousin, West. Reading his earlobes, Samantha decides that things comes easy to Cay, unlike West. Cay is very outspoken and at times impulsive, saying and doing things without considering the possible consequences. For example, he tells Sammy that the only “Chinaman” he has ever seen before was in a circus (56). He also jokes constantly, calling West “chicken” to goad him into arm wrestling (57), or calling Peety’s pantalones (Spanish for pants) “pantaloons,” which were either foreign or women’s clothing (57). It is also Cay’s idea that whichever group loses the fishing bet will have to sing “Yankee Doodle” unshucked, which means naked (90). While he is a friend to Samantha, Annamae, and the cowboys, he hence exhibits oppressive structures, such as racism and patriarchy, that Lee explores in the novel.

When Andy tells her stories, the others often try to guess at their lessons. At times, Cay’s guesses are the most simplistic because he interprets the stories too literally. West calls him a dummy and offers a deeper reading of the story. However, the snake and rabbit story (meant to represent Samantha and West, who are born in those years, respectively) is closer to Cay’s area of expertise: romantic love. Cay suggests that the two lovers should have run away together, which is closest to Samantha’s understanding that nothing can get in the way of true love. When he speaks to Samantha about the difficulty of finding the right girl, she understands the meaning but misunderstands who Cay is discussing; Cay is not talking about himself but rather about West. In fact, she doesn’t realize this to the very end of the story, just before West confesses his love for her. While Cay is presented as superficial, he is perceptive beneath his curly hair and green eyes, and Lee uses him to drive the romantic subplot between Samantha and West accordingly.

The final member of the cowboy trio is the wrangler, Peety. Cay jokingly introduces him as Pedro Hernando Niña, Pinta, and the Santa Maria Gonzales to make fun of Mexicans having so many names compared to Anglos. While in jest, this introduction shows to the reader that Peety has a marginalized experience on the trail. The middle names that Cay uses are the names of the boats used by Columbus when he explored the Americas, paving the way for European colonialism; Lee hence creates a subtext that highlights the originals of the forms of oppression that Peety and other characters experience on the trail.

Peety’s presence adds another layer of American history to the story: the history of Mexico and the United States. Texas, which is where he comes from, was part of Mexico until it was officially annexed after the Mexican-American War in 1848. Peety’s first language is Spanish, and that is the language that he uses when he sweet-talks the horses. His sense of his heritage contributes to the novel’s theme of Race and Racism in the Westward Expansion. Mexicans, according to Peety, do not harbor the same racism as Americans, countering Cay’s belief that “Chinitos” (young male Chinese) should marry “Chinitas” (young female Chinese). Peety proudly says that Sammy can find a nice Mexicana to marry in California because Mexicanos consider their heritage as Aztec and European. When it is revealed that the cowboys already knew that Andy and Sammy were girls disguised as boys, Peety reveals that his friendship with Andy has blossomed into love and a marriage proposal.

Isaac is Andy’s older brother. They are separated when the siblings are sold to a new enslaver. Isaac was a kind older brother. He taught Andy how to make good bobbers for fishing and gave Soapy, the piglet, to their younger brother to reward him for overcoming his fear of horses. Isaac has an optimistic personality, always looking for the positive in a situation and helping his siblings to do the same. He gave Tommy the rock with the hole that Andy now wears on her charm bracelet, and told his siblings that if you “looked at a person through the hole, [you] could see the good in them” (173). This lesson reflects the bonds that form throughout the novel on the trail.

Later, Lee reveals Isaac’s alter ego, Badge. He is part of the Broken Hand Gang and was featured on the same “WANTED” bulletin as the cheongsam-wearing Samantha. While he did not commit all the crimes of which he was accused, he believes himself morally responsible. As someone liberating himself from enslavement, he is seen by society as guilty, reflecting Lee’s exploration of the power of perspective in historical narratives. When Isaac throws himself off the cliff while clutching both of the MacMartin brothers, he likens himself to a falcon. He also accuses them of being “cannibals” since they came to Harp Falls as bounty hunters. Samantha wonders if she is seeing an angel. When he falls, he only kills one of the brothers, but his action does give the girls enough time to get weapons and fight back rather than be killed immediately by Angus. Isaac is presented as a caring brother driven to a life of violent acts through the desperation of an enslaved man for freedom.