The Coldest Winter Ever

Ricky, also known simply as Santiaga, is Winter’s father. In the beginning of the novel, he is Brooklyn’s most prominent drug lord, but he quickly ends up with life in prison. Winter describes him as charismatic, handsome, and a family man. Santiaga gave his family a life of luxury before being imprisoned, yet during his incarceration it’s revealed that he had been having an affair with a younger Puerto Rican woman, with whom he had a son named Ricky Santiaga, Jr. The affair and baby represent the fact that his family didn’t know Santiaga as well as they thought they did. In this way, Santiaga can be characterized as a secretive man. Santiaga looked at his drug business as a game of chess, and he often used the game to strategize his business plans. By giving the pawns, such as Midnight, stakes in the game, he created loyalty and allowed his business to flourish. For many years before being caught, Santiaga was a successful businessman, and Winter always points out that he earned respect from everyone he met. This concept of respect resonates with Winter, who tries to emulate her father.

Momma had Winter when she was 14 and considers herself a “bad bitch” (4), or a woman who uses her beauty to get what she wants from men. Momma is all about looks and makes it her full-time job to be beautiful by continually doing her hair and buying the most luxurious clothes and jewelry. She acts more like a friend to Winter than a mother, often gossiping and partying with Winter rather than giving her motherly advice. Momma loses her beauty after being shot in the face, a problem exacerbated by becoming addicted to crack once Santiaga is imprisoned. When Momma dies, she is unrecognizable to her family from the years of degrading drug abuse.

Although Midnight sells drugs for Santiaga, he is different from the other drug dealers that Winter knows. Unlike other men, Midnight rejects Winter’s sexual advances and doesn’t flaunt his wealth. Instead, he hides his money away, lives humbly, and is attracted to women who read books and think critically. Midnight later adopts Winter’s two youngest sisters, giving them a chance for a wholesome, God-fearing life.

Sister Souljah is both the author of the novel and a nonfiction character. She is a civil rights activist who speaks publicly about what it means to be an African American community. Souljah’s sister describes her as someone who likes to take in people with problems, but Souljah has a big heart for young people who are lost. Souljah is trusting in that she lets Winter move in without any stipulations, but she is also very aware because she keeps files on everyone she interacts with, ultimately finding out their background. As a character, Souljah is the opposite of Winter. Souljah is never seen as selfish, as she is constantly busy trying to help the community around her. 

Natalie was once Winter’s best friend, but Winter betrayed her over a man. Previously, Natalie filmed a video of Winter in a hot tub with Slick Kid and Bullet—a video which Midnight later disgraced Winter for. Natalie is best described as a gossiper. Winter meets Natalie again in prison, as the girls Winter grew up with are now incarcerated, presumably for their connections to drug-dealing boyfriends.

Rashida is the only girl at The House of Success who cares about Winter. Rashida is the one who introduces Winter to Souljah in the hopes that Souljah can help her. Rashida is described as beautiful, but she hides her beauty behind books. Rashida admits she has never had sex consensually and considers herself a virgin.

While Winter sleeps with many men throughout the novel, Bullet is her only actual boyfriend. While he claims to love Winter, he is extremely jealous and abusive towards her. He ultimately allows Winter to be arrested for his illegal activities.