Hot Take on The Coldest Winter Ever by Sister Souljah

The Coldest Winter Ever by Sister Souljah wasn’t the cautionary tale it was meant to be

When I first read The Coldest Winter Ever by Sister Souljah many years ago, I was blown away by Winter Santiaga’s story. Winter was raw, unapologetic, and she represented many young girls in a fundamental way. She showcased how we all thought about things when we were seventeen. Regardless of our backgrounds, there is a crossroads going from a girl to becoming a woman.

I was always intrigued about what would happen after Winter’s mandatory 15-year sentence. So when its sequel, Life After Death, came out back in March, I knew I’d have to refresh by re-reading The Coldest Winter Ever. I got some new insights about this book that I never even noticed the first time around. 

I noticed some very problematic themes and storylines reading it a second time after a few years had passed. These are my hot takes; I believe TCWE wasn’t the cautionary tale for young Black people that Sister Souljah intended it to be. 

Hot take #1: Sister Souljah is Preachy 

The first time I read this, I thought that Winter was a brick. I believed she should’ve just listened to Souljah’s advice and guidance. After a second read, though, I realized how full of shit this fictionalized Sister Souljah was. Let me explain. 

Sister Souljah’s literary self could make issues sound impactful, but all she did – literally – was talk. She preached at Winter, as well as the audience and the youth girls group. Souljah made herself and her way of living the standard. 

Sister Souljah came off as hyperjudgemental. For example, she freaked out before an public speaking event with HIV-positive women at a women’s prison. She was grossed out that she had to even be in the same room as women with “it”. Even though she just raised money for HIV patients at a benefit a few weeks prior. 

Winter even mentions that to her, but Souljah doubles back by saying she was working with “professionals.” (the doctors) Alright. She starts her message to these with “I know you all used to be pretty.” Excuse me, Souljah? She says a lot of fluff and everything she says in TCWE is just like that. No substance, just rhetoric. Rhetoric that is neither practical nor relatable. 

Hot Take #2: Winter’s Lifestyle Disgusts Sister Souljah

She basically affirmed that the best way was her way or no way with her preachiness. Sister Souljah fails to realize that not everyone has the privilege to make better choices in the moment. Sometimes, Black girls and boys have to pick from outrageous circumstances that no one would ever want to have to make. 

For example, Souljah led a youth girls group in her home. A group where she talks about alternatives to the “fast life” and overall being a more bonded community. Souljah’s mentality in TCWE is community over the individual. The girls were not interested. If it wasn’t their family or friends, it wasn’t their problem.

To be fair, when you’re trying to survive, you and yours are the first people you think about. The last thing you should be doing is trying to save the world when you can’t even save yourself.  

I believe Souljah had some noble ambitions. While this may true, you can’t save someone that 1) doesn’t want to be considered in your equation of sainthood. And 2) until your personal needs are addressed. This is the part that went over the fictionalized Sister Souljah’s head in this book. She saw the big picture, but she didn’t see the girls’ lives and how they grew up to think. 

Even if those girls did everything “right,”(go to college, get a blue collar job, even become an activist, etc.) their dreams would be – to some capacity – just a bit out of reach. Black women and men’s dreams weren’t in the system’s designs. I didn’t want Souljah to make them victims, but I wanted her to be honest about that underlying factor. 

So for Souljah’s character (and perhaps even herself in real life) to judge these girls so harshly is harmful to say the least. As a teacher, educator, and mentor, you are supposed to spread these positive messages to grow, yes. However, when it comes down to it you have to meet your students where they’re at. No one can get to the top of a mountain in one step. Souljah’s character was no teacher. She was a decent role model, but more so a captain-save-a-hoe with a hint of self-righteousness. 

Hot Take #3: This is Not a Cautionary Tale (Until It’s Too Late) 

According to Sister Souljah, this book was meant to be a cautionary tale to young Black girls and boys. However, many readers said that when they were younger, they glamorized Winter. The readers didn’t realize how messed up the story was until they re-read it as an adult. They didn’t realize that until it was too late – as some had reread it in prison, the opposite desired effect.

Winter’s life was glamorized: the glorious sexcapades, the excitement of her fast-living, the drama, the hustle, the Hip Hop scene, her seemingly flawless and endless beauty and fly fashion. Although many adults realized that Winter was completely delusional about her life, the world, money, and so much more; many teens and young adults did not. In the grand scheme of life, Winter’s actions wouldn’t really amount to much, but to her, it was very exciting. So we – the reader – could possibly be excited with her. 

What I believed happened is the fact that instead of a more neutral perspective with thoughts from the range of characters, the reader spends the majority of the time in Witner’s head. Who – we all know – is a little delusional when it comes to what is really going on beyond her outfit, drama or money flow problems. 

Ironically, Souljah made Winter too likeable. Winter made bad decision after bad decision, and we all probably wanted to slap her upside the head at some point in TCWE. Because we could empathize with her, we wanted to see her win and get it together. That’s just how stories work; why do you think we all fell in love with Killmonger? 

People were devastated that Winter got locked up for Bullet’s foolery, although she had been on a slippery slope of criminal activity herself. That’s life, though, but as teenagers (and most readers quite frankly), we weren’t thinking about that. 

Most of us got excited from Winter’s flyness, confidence, the way she had sex, the way her friends seemed to worship her and were even jealous of her, the way she could use men to her whim to get whatever she wanted. Winter was the orignal femme fatale in street literature, and readers – especially young ones – ate that shit up. 

Who doesn’t love being a “bad bitch”? 

Sister Souljah played herself by making Winter the protagonist. It would’ve been more effective to have dual protagonists to show the duality of two lifestyles. Maybe even potentially between Porsche and Winter, and up Porsche’s age so they can both be teenagers at the same time. (Because we did NOT need A Deeper Love Inside). Porsche was more tamed, and did things the “legal” way, while Winter was more wild and risky, always opting for “illegality.” 

If Porsche was just as pretty, fly, and wealthy – but moved differently – maybe there could be another way to survive. And better than that: succeed. If that was actually Souljah’s intent, but I get the feeling that that wasn’t Souljah’s sole intent for writing this book.  

You see, folks need a more direct message if you were trying to reach a younger audience. Ages 11-17 may not catch the underlying subtitles like an adult would. So, a paralleled perspective was needed to counter Winter’s shenanigans and get out of her own excitement and desires. 

Hot Take #4: Sister Souljah Hates Winter Santiaga

Winter – although it seemed like she just didn’t “get it” at times – was actually full of potential, and had a natural aptitude for fashion and beauty. The closest Winter ever got in TCWE to capitalizing on it was when she had her friend Simone boosting clothes from high-end stores, then selling and styling girls from the group home. She even included facials, nail services, and getting their hair done. 

I was wondering when that “aha” moment would be for Winter to make fashion a potential business. When would she realize she could make bank and have the glamorous life of her dreams if she pursued fashion from a business hustle mindset vs a street hustle mindset? Have you seen the lifestyle of some fashion designers? It was in the realm of possibility, just not for Winter. She repped Brooklyn through and through. Fashion and beauty were means to an end.

I believe that some of Sister Souljah’s intent – as a writer – wanted us to hate Winter, though. She wanted us to look at Winter like she was dumb, and silly, and a complete bird from the projects. Winter could be all of those things, at times, just like anybody else in her neighborhood. There was never anyone around her that served as a lifeline to wake her up and give her proper guidance.  Yes, Winter’s bad decisions lead to bad circumstances, and Winter should be held accountable now that her father isn’t around to save her. 

However, when a supposed lifeline that is Sister Souljah does show up, it seemed like she’d rather judge Winter then help her. (recommending college to someone that has barely been in school for years and doesn’t care about it is just foolish and unhelpful) 

Everyone Winter came across took advantage of her (whether her body, money, or status), and Souljah the writer wrote her as a naïve, oblivious teenage girl. That part I understood, because who didn’t make crazy mistakes at seventeen? Why did Winter have to keep getting punished? Especially when there were so many opportunities to pivot into a better situation after so many bad ones. (i.e. when she was about to visit Midnight in Maryland and gets a call from Bullet right before she gets on the bus. The Bullet that put naked footage of her in a bar in Brooklyn and set her family up.) Was she just really that dumb?

Even in life, there’s always that one person that can be a lifeline to help you get through what you’re going through and help you wake up, but in this story, it was Winter against the world. In my opinion, the author wanted Winter to suffer horribly and never learn from her mistakes because she needed to be punished instead of redeemed. That’s the story I believe Sister Souljah was trying to tell. Winter had so much potential, and it seems like Souljah wanted to sniff her light out completely. That’s my hot take on that one. 

Hot Take #5: Sister Souljah is a Borderline Narcissist

A narcissist is “someone that has an excessive interest in or admiration of themselves.” Who writes themselves as themselves into a novel?

In an interview with Shondaland, Sister Souljah says this: “If you go back to The Coldest Winter Ever, you’ll see it opens up with Winter Santiaga clearly saying how much she hates Sister Souljah. There’s a reason for that. I didn’t want people to confuse me with the character. Because Winter is not my life story. And my life story is nothing like hers. Winter’s mindset is not my mindset. Winter’s choices are not my choices. But I think one of the things a person who aspires to be a great writer has to do is they have to be able to separate themselves from the characters to give their characters authenticity.”

If Sister Souljah truly believed that, she wouldn’t have written herself into the book in the first place. To mention herself on the very first page inserts her presence whether it’s “her story” or not. Souljah seems to care about her morals and self-image so much that she had to write herself as antagonist to Winter to prove she could never be like Winter. That’s a little weird, and no one asked for it. There is no logical reason to have written herself in the book in the first place. Sister Souljah’s character could’ve literally been anyone else, maybe with a less judgemental personality.

I believe Souljah was also even a bit resentful of families like the Santiaga’s, because she grew up in “fear” of the drugs in her own neighborhood. Souljah probably just wanted to feel safe, and felt as if drug families were making it harder. Women like Winter are making it harder for women like Souljah. This translated to insecurity. Winter’s extreme level of selfishness coupled with her use of her body to get what she wanted seemed to irk Souljah.

Hot Take #6: Midnight Was a Clown

Why doesn’t anyone talk about how Midnight adopted the Santiaga twins (the youngest), but couldn’t even be bothered with Winter or Porsche? Who both were in the same predicament?

The only reason he was able to leave the “life” without going to jail was because of Winter’s father. And this man left Winter and Porsche for dead. He told Winter when she asked to come with him “hell nah, you’d just slow me down.” 

Her father is the only reason Midnight was even able to leave, but his daughter is just some bird who deserves to roam the streets with the crumbs you gave her, a mother on crack, and three sisters in foster care?  

It’s interesting how Midnight fell so hard for Sister Souljah’s character, sending her letters for months trying to ignite a relationship. Sister Souljah was the only Black woman Midnight has ever seemed interested in. We couldn’t even see him with a princess from his home country I guess. 

Sister Souljah judged Midnight’s lifestyle critically. She said there had to be a “catch” for a Black man carrying himself with so much masculinity. Because he’s a drug dealer, unlike the college Black men that she knew that seem way less masculine. It’s almost like she wanted someone as fine and confident as Midnight to like her because she was the kind of girl the “real men” should like. Not every school boy is a corn ball and nonmasculine, and not every hood nigga is that confident and overtly-masculine. Then for her to say, “sorry, I don’t believe in drugs and that life. I don’t feel sorry for you. Leave me alone.” The ego. Do you like Midnight, or not? You don’t have to say no with judgement; it’s unwarranted.

Midnight loved to act like he was so different from the other men on the block, when he was slinging dope the same as everyone else. And Sister Souljah judged him fiercely for it. This was very ironic.

What’s even more interesting is how much Midnight admired Souljah for her “community work” fighting for the community. Yet, Midnight continuously disrespects the men and women from the disenfranchised community that he’s from, rolling his eyes at them, calling them low lives. Yet, he admires Souljah for trying to “save them”? Noted. It’s even more astounding because Souljah’s “work” is just her empty, corny tangents and fundraising for issues that seem like they’re never solved.

Winter was very interested in Midnight, and yet, he was borderline obsessed with Sister Souljah. It was a written as if a man like Midnight (a desirable Black man with money and masculinity) could never love a woman like Winter, even though they were more alike than he would’ve liked to admit. Neither did G.S. – who was ready for a good time, but had “love” for Souljah. The message is clear: men in this book love moral women like Souljah, and love to fuck girls like Winter.

And the way Midnight treats and speaks to Winter made me infuriated. Winter wasn’t always the most interesting conversationalist, and the first time around, I adored Midnight. I believed he was one of the few men on the block that had his head on straight, and for the most part, he did. But he treats Winter like her father didn’t save his life. This is your mentor’s daughter – a mentor that gave you a job straight out of jail when you couldn’t survive and protected your life over his own. Midnight bumps Winter, he rolls his eyes at her, he verbally disrespects her, then turns around and kisses Souljah’s ass when Souljah disrespects him? Winter never gave Midnight a reason to treat her like the bottom of his feet, but Souljah did and that didn’t sit well with me. 

 Far too long people from these neighborhoods will idolize a woman (or man) that has “made it out of the hood” when she was no different from the women/men you grew up with. They just had different choices, and thus moved differently. Given the reason and circumstances, anyone has the potential to make different choices. He was a clown, and overly judgemental when he was literally no better.  

The fact that he was even able to leave with no scratches while Winter fought in the jungle of Brooklyn became troubling as well.

Petit Hot Take: Sister Souljah Had a Ghostwriter 

In the sequel to The Coldest Winter Ever – Life After Death – we do not see any growth from Winter. Winter doesn’t even sound like a woman from Brooklyn, whether she was in prison or not. Her entire personality seemed off, and the writing style was not even in the realm of similarity, and not in a good way. 

Final Thoughts

As a writer, I know you’re not supposed to blame the writers for what the characters say, but this book felt personal. And some of the things said about Winter felt very personal. 

Of course, these are just some of my critiques and observations that I found very problematic. With the author as well as the characters and storyline. Things that don’t seem to be addressed too often in discourse about this book. The subtleties Souljah tried to give to “caution” were inaccessible to the young mind.

I still love The Coldest Winter Ever. But it’s worth analyzing some of the deeper motivations the author had for writing this book, and how some of the implications could translate to young readers that don’t know any better. Hopefully I provided a deeper insight into a timeless piece, and gave the hots takes on a progressively nuanced discourse for fans and avid readers.

Tags: hot takes sister souljah, the coldest winter ever, literary analysis, femme fatale

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