Set in the projects of Brooklyn, New York, The Coldest Winter Ever is the story of Winter Santiaga (aptly named because she was born during one of New York’s worst snowstorms), the rebellious, pampered teenage daughter of a notorious drug dealer. Ricky Santiaga, Winter’s father, has attained substantial wealth through his illegal drug empire and lavishes his wife, Winter, and Winter’s three younger sisters, Porsche, Lexus, and Mercedes, with the best things money can (and cannot) buy. Unknown to her father, Winter uses her hustling tricks to get whatever she wants.
Winter’s world is turned upside down on her 16th birthday, when her father suddenly decides to relocate his family and his growing business to Long Island, but she is determined not to sever ties with the old neighborhood. Her life spirals downward when her mother is shot in the face by foes of her father. Shortly afterward, the FBI arrives at the Santiaga mansion while Winter is at a party, seizes the family’s possessions, and sends the drug lord to prison. At this juncture, Winter’s sisters are placed in child custody, rather than in their unemployed mother’s custody.
Winter escapes by pretending to not be her parents’ daughter. Winter stays with a man just for his money for a while, but when his girlfriend comes back, Winter goes to live with an aunt. While with the Aunt, Winter’s location is revealed, and she is turned over to the Bureau of Child Welfare. Winter’s location was probably divulged by Natalie, a former friend of Winter’s, who suspected that Winter was trying to date her boyfriend. While visiting her father in jail, she finds out that he had an infant son and was cheating on her mother, which tears her apart. Also, her father murdered someone while in jail.
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 her from hustling: she makes money by selling clothes and cigarettes to her housemates, and she does their hair. Winter obtains the goods she sells from her friend Simone, who is a booster who steals designer clothes for her. Winter continues making money this way until Simone is arrested. Winter does not bail out now-pregnant Simone, but Simone gets out another way. Upon her release, Simone gathers some friends to wait so that they can beat up
Winter. Winter escapes the beating by running and never returns. Then Simone falls and has a miscarriage. Rashida, one of Winter’s House of Success housemates, thinks that Winter needs help and persuades her to go to a friend’s house. Winter doesn’t know that the friend is Sister Souljah, whom Winter boldly stated she never liked in the book’s introduction. Under Souljah’s tutelage, Winter volunteers at a benefit for people with HIV/AIDS, but Winter still does whatever she can to get money. Winter steals money from the AIDS benefit and rushes home to pack.
Suspicious of Winter leaving, Lauren, Souljah’s sister, switches the bag into which Winter has put her prized belongings. Winter takes a cab to a New Jersey hotel, and realizes that she has no money, no jewels, and no protection. Winter hooks up with an old boyfriend named Bullet, who has money. She finds out that she is pregnant with the baby of a man who tricked her into believing he was hip-hop MC GS. Months later, Winter’s world crashes again when she is attacked in a car by Simone. A crowd gathers to watch the fight, and Winter loses focus when she sees Bullet cause the crowd to disperse by waving a gun in the air.
Once Winter looks away, Simone slashes her across the face with a broken bottle. Winter is led back to the car by Bullet and, shortly afterward, the police arrive. Bullet leaves Winter, who gets a mandatory 15-year prison sentence for transporting drugs in his rental car. Soon, her old friends Natalie and Simone join her in prison, and her younger sister eventually becomes just like her. The ending surprises: after her father was jailed, Winter talked about being let out of prison to attend her mother’s funeral.
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