Lana Santiaga: Winter's mother who is more sister than mother. He is depicted as an initially successful man who lets greed and his vices overpower him.

Ricky Santiaga: Winter's father and he is depicted as a man who lavishes attention, love, and material gifts on the women in his life, while being a calculated and violent drug lord. She is an advocate and role model for young black men and women. In the novel, she provides a home for a displaced Winter. Sister Souljah: A fictional portrayal of the author herself, who advocates for the improvement of black communities. As such, she seeks revenge, resulting in an escalating rivalry that becomes violent. She is eventually arrested while pregnant and is angry when Winter turns her back on her. She is initially a coconspirator of Winter's as they are involved in illegal activities together. After her father is arrested, Winter encounters much more strife, and eventually lands up repeating many of the mistakes and experiences of her parents. She is highly focused on attainment of material wealth and is also sexually promiscuous. The story follows her life, first as a pampered child and adolescent of questionable morality. She is born to a teen mother and drug lord father during extreme winter weather. Winter Santiaga: The protagonist of the story. Winter takes up the skills she learned from her father to maintain her lifestyle, such as selling illicit items in the girls’ home to make money. This all changes when Winter's father is arrested for drug trafficking, and Winter finds herself in a girls’ home. Due to the power of her father, Winter is infamous in her neighborhood, and she uses her power to get what she wants. The story is told from her perspective in slang that is highly influenced by the hip-hop culture.

Winter is brash and self-important she says, 'it was important for me to know I deserved the best, no slum jewelry or knock-offs'. The main character is Winter Santiaga, the teenaged daughter of Ricky Santiaga, a local drug kingpin. The Coldest Winter Ever is a 1999 novel by Sister Souljah published by Simon and Schuster.

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