The Coldest Winter Ever
Sister Souljah
ISBN 0-7432-7010-X
Washington Square Press, 1999
Urban Fiction

Winter learned to hustle from the best, will it be enough to keep her alive?


Winter Santiaga has it all: the looks, the money, the power, and the home. These are the things that matter to Winter. Winter’s father, Ricky, is a successful gangster in New York, who taught his wife and children the art of hustling. But the the Santiagas’ world is quickly turned upside down beginning with a shooting where the mother is shot in the face.  Mrs. Santiaga is destroyed by wound; her beauty is ruined and she forms an addiction to painkillers. Santiaga is arrested along with most of his street army. With no one to turn to and limited reserves of money and resources the Santiaga family implodes. Winter’s sisters, Mercedes, Porsche, and Lexus, are snapped up by child welfare and sent to foster homes, but Winter evades the system, ever a hustler. She lives with an older man for a while, followed by a stint with an aunt. At her aunt’s she is reported to child welfare and placed in the House of Success, a group home for girls.

She continues hustling at the home, employing Simone, a friend from Brooklyn to steal items that she re-sells to the House of Success residents. Simone, pregnant, is arrested and Winter refuses to put up bail. Simone is released and brings a crew of girls to the House of Success to beat Winter up. Winter escapes and runs away, but Simone falls and eventually miscarries. Another resident of the House of Success advises winter to stay away and takes her to a “friend’s” house for refuge.

It turns out this friend is Sister Souljah, a political activist whose message Winter despises. Even with an opportunity to grow and perhaps change her destructive path, Winter continues on the road to self destruction. She hustles those who want to help her. Unfortunately, Winter’s hustle at Souljah’s fails when Souljah’s sister switches their bags, leaving Winter with nothing. Forced to leave Souljah’s house, Winter runs into Bullet, a man she dated previously. They rekindle, after all, Winter needs a place to go. Bullet arranges a big, final hustle that will allow he and Winter to set out on their own. The deal is a bust, Winter lands in jail and Bullet walks free.

Prison. This had to be where Winter was headed all her life. She is joined by friends and family from Brooklyn, everybody she knows is there. Released on a pass to attend her mother’s funeral, Winter reunites with her sisters, the eldest of whom is just like Winter. It is not until the very end of The Coldest Winter Ever that Winter realizes her mistakes and learns a lesson or two.


The Coldest Winter Ever was kind of like a relentless tapping on your shoulder. Not painful, but definitely annoying. Winter is awful, but you still root for her as she makes bad choices again and again. Witnessing her downward spiral is painful and emotional. She has no respect for herself and thus gains little from others. Sister Souljah effectively illustrates the problems of crime and the cycle of crime, abuse, and beliefs that the Santiaga family is absorbed by.

Curriculum Ties:

An interesting English class assignment would be to pair this novel with another epic family tale, something more conventional such as 100 Years of Solitude by Marquez.


Explicit sex, language, violence, crime.

This is an adult novel, so challenges to it might be rare. I would not shelve it in a YA section. Should a challenge arise from a teen reading the novel, (or any other reason), ask the challenger to read the entire novel and think about the message that Souljah is trying to communicate. Highlight the important place that The Coldest Winter Ever holds in the urban fiction genre and the role that this genre can play in the reading lives of urban youth.

Selection Rationale:

The Coldest Winter Ever is cited again and again as a groundbreaking novel. It is a classic in the urban lit genre.

“Although the novels writing is amateurish, the message is sincere.” – Library Journal

The Coldest Winter Ever is a fast-moving, impeccably brilliant account of choices and consequences within the urban hip-hop culture. Sister Souljah writes eloquently with expressive insights and language of youth. Amidst the crisis and cruelty of inner city poverty and seemingly insurmountable struggles, Sister Souljah’s voice is one of grace and unmistakable clarity in one young woman’s coming-of-age story.” – Magill Book Reviews


Read the final paragraph, Winter on her sister, page 284.

Construct an opinion of Winter from Midnight’s point of view.

About the Author:

Sister Souljah, born in the Bronx, is an activist, musician, author, performer, and film producer. She is the author of three books. Souljah lectures on many topics about relationships, self-esteem, and rights in the African-American community, as well as diversity and coalition building.