The Coldest Winter Ever is a best-selling 1999 novel written by rapper and activist Sister Souljah. Set in the projects of Brooklyn, New York, The Coldest Winter Ever is the story of Winter (aptly named because she was born during one of New York’s worst snowstorms) Santiaga, the rebellious, pampered teenage daughter of a notorious drug dealer. Winter’s father, Ricky Santiaga, has attained substantial wealth through his drug empire and lavishes his wife, Winter, and Winter’s three younger sisters, Porsche, Lexus, and Mercedes, with the best things money can (and can not) buy.
Unbeknownst to her father, Winter has picked up on all of his hustling tricks and does whatever is necessary to get what she wants. Winter’s world is turned upside down, however, on her 16th birthday when her father suddenly decides to relocate his family and his growing “business” to Long Island, but Winter is determined not to sever ties with the old neighborhood. The downward spiral in Winter’s young life begins when her mother gets shot in the face by foes of Santiaga. Shortly afterward, the FBI arrives at Santiaga’s mansion, seizes all of his and the family’s possessions, and the drug lord is sent to prison.
It is at this juncture that Winter and her sisters are placed in the custody of the Bureau of Child Welfare (the girls are not placed in their mother’s custody given the fact that she was unemployed). Refusing to live in a foster home, Winter goes to live with an aunt; the tables are turned on Winter when her aunt steals all of the money Winter has left, and her former best friend, Natalie reports her to the BCW as revenge and Winter officially becomes a ward of the state. After being taken out of her aunt’s home, Winter starts living at the House of Success, a group home for teenage girls.
Her new surroundings do not stop Winter from hustling; she makes money by selling her housemates clothes and cigarettes and doing their hair. Winter’s main source of income, however, comes from her pregnant friend Simone, who becomes a booster by stealing designer clothes for Winter. Seeing that the House of Success was not where she wanted to be, Winter ventures out into the streets of Brooklyn once again, determined to make it on her own. One of Winter’s housemates, Rashida, thinks that Winter is in need of help and persuades Winter to go to a friend’s house with her.
Little does Winter know that the “friend” is Sister Souljah, whom Winter boldly stated she “never liked” in the book’s introduction. While under Souljah’s tutelage, Winter does things such as volunteer at a benefit for people with HIV/AIDS, but seemingly Souljah’s efforts are all for naught, because Winter is soon up to her old tricks again. Months later, Winter’s world comes crashing down around her when she reunites with an old boyfriend, Bullet, who has now replaced Winter’s father as Brooklyn’s drug kingpin.
While in the car waiting for Bullet, Winter is attacked by her former friend, Simone, with a brick. A crowd gathers to watch the fight, and Winter loses focus when she sees Bullet disperse the crowd by waving a gun in the air. Once Winter looks away, Simone slashes her across the face with the broken bottle. Winter is led back to the car by Bullet, and shortly afterward the police arrive. Bullet leaves Winter to take the fall for him, and she is given a mandatory 15 year prison sentence after she is arrested and convicted of transporting drugs in Bullet’s rental car.