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A Masterclass in Morally Gray Character Development: Raymond Reddington—a case study


Hi everyone, welcome back to the Chronicles & Coffee blog! Today's article is written by Anca Antoci, fantasy author, book blogger, and BBNYA panelist. Make sure to follow the links at the bottom of the article to find more out about her after reading this amazing article. As well as so, check out her page to see my featured article as well!

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A Masterclass in Morally Gray Character Development: Raymond Reddington—a case study.



I know I’m not the only one but find myself drawn to morally ambiguous characters in books and movies all the time. Despite their flaws, these characters possess a skewed sense of morality that can make us root for them to succeed. However, when it comes to writing, I find it not so easy to flesh out such a character in a way that is believable and multilayered. So my first thought was that when I find such a character, I would stop and analyze it to understand what makes him/her so appealing and use this information to create better characters in the future.

Occasionally, I stumble upon a character so deviously cunning and irresistibly charming that I’m hooked. And even though some of the heinous crimes he conducted are hard to justify or forgive, you feel tempted to look the other way. When that happens, I want to take that character apart and see how I can construct him again and make my own. Why? Because I want to write a morally gray character, my readers can fall in love with.


The greatest morally gray character I came across recently is Raymond Reddington from Netflix’s The Blacklist. Now, if you haven’t watched the show, but want to create a compelling morally gray character, I recommend you give The Blacklist a try if not for its entertainment value, at least for research purposes.


Raymond Reddington and The 48 Laws of Power—a case study


Raymond “Red” Reddington from Netflix’s “The Blacklist” is a remarkable morally gray character due to the perfect balance of charisma, intelligence, and enigmatic nature he possesses. Reddington’s allure lies in his ability to navigate the fine line between hero and villain seamlessly.


He is a master manipulator, effortlessly blurring the boundaries of right and wrong to serve his own agenda. With a captivating mix of charm, wit, and ruthlessness, Reddington keeps audiences hooked as they grapple with their conflicting emotions towards him. His complex motives and the occasional glimpse of his hidden compassion make him an intriguing enigma, forcing viewers to question their own moral compass and challenging conventional notions of justice.


Reddington’s morally gray nature is what makes him an unforgettable and compelling character, leaving audiences captivated by his every move. While he admits to having killed many people, he also insists that he didn’t kill anyone who didn’t deserve it. Here’s a quote that stuck with me “The world is rarely a fair place and that’s why it needs people like me.”


I was recently reading “The 48 Laws of Power” by Robert Green — a book that stirred up quite a controversy as many deemed it a guide on how to manipulate people. By this time, I had already seen the first six seasons of The Blacklist. And as I was reading this book, I couldn’t help but see the parallels between many of these laws and Redington’s character. It was almost as if the screenwriters had used Green’s book to flesh out the perfect character. I’m not saying that they did, but it sure looks like it.


Now, if you’re not familiar with the show and the character, you’ll have to take my word for it, or go and watch a few episodes, then come back and read this again. But if you know Reddington, this will make so much sense. And if you also read The 48 Laws of Power, you’ll see the connection. By the way, I recommend the book either for self development or as research into creating outstanding characters for your books. A warning though, if you pick up the audiobook, be aware it has annoying background music that I found distracting.


I’m not going to delve into all 48 laws, but I will pick up those which stood out to me in regard to Reddington’s character. If you’re a writer and looking to learn how to flesh out a morally gray character, I hope my analysis will help you pinpoint some traits to lend to your characters.


Law 1: Never Outshine the Master

Raymond Reddington understands the importance of appearing subordinate when necessary. Despite his immense knowledge and skills, he often maintains a respectful and seemingly deferential attitude towards those in power, such as the leaders of criminal organizations or government officials. By doing so, he avoids triggering their insecurities and maintains his advantageous position. A great example is Reddington’s attitude towards Berlin in season 2. He avoids overshadowing Berlin’s authority, allowing him to gather valuable information and maintain a strategic advantage.


Law 2: Never Put Too Much Trust in Friends

Reddington is aware of the potential dangers of trusting others completely and I think he’s said at least once in the first season that he doesn’t have friends. “Lizzie, don’t be ridiculous. I don’t have any friends.” I would argue that he considers Dembe a friend, though. He strategically cultivates alliances and friendships, but remains cautious and never reveals his full hand. He understands that loyalty can be fickle, and he constantly evaluates his relationships, ready to adapt or sever ties as needed to protect his own interests. Elizabeth sums it up in this quote: “You’re a loner, you keep your distance… you travel freely through foreign lands… you’re rootless, your closest friends are strangers… you understand that tight bonds make you vulnerable so you’re careful not to have any.”


Law 3: Conceal Your Intentions

Reddington is a master of manipulation and deception. He often conceals his true intentions and motives behind a veil of mystery and misdirection. Reddington surrenders to the FBI and insists on working only with rookie profiler Elizabeth Keen. He conceals his true motives for targeting specific criminals and his connection to Elizabeth, manipulating the FBI task force’s perception of his intentions. As he tells Elizabeth in the pilot episode, “Let me put your mind at ease. I’m never telling you everything.” Besides, every time he gives the task force a Blacklister, he’s pursuing his own agenda and more often than not, they have no idea what that means.


Law 5: So Much Depends on Reputation — Guard It with Your Life

Reddington understands the power of reputation. He meticulously curates his image as a dangerous and influential criminal mastermind, which both intimidates his enemies and attracts potential allies. Reddington carefully guards his reputation, as it allows him to command respect and ensures that others are hesitant to cross him.


Law 6: Court Attention at All Costs

Reddington is a charismatic and flamboyant character who effortlessly commands attention wherever he goes. He is aware of the influence that attention brings and strategically uses it to his advantage. By being the center of attention, Reddington can manipulate and control the narrative, ensuring that he remains a key player in any situation.


One thing that my husband finds annoying is that in tense moments (like before executing an enemy) he tells a story — something from his youth, or from his extraordinary adventures. While I’m not necessarily fond of these stories because the timing seems wrong (tense moment, remember?), I can see why he does it. Reddington’s penchant for telling stories before executing his enemies serves several strategic purposes. First and foremost, it allows him to establish control over the situation. And also he liked to put on a good show. Second, his stories serve as a psychological tool to unsettle his adversaries because they’re so out of the blue. And third, it also serves as a form of psychological warfare. Through his tales, he often reveals hidden truths or personal insights about his enemies, exposing their vulnerabilities and demonstrating his superior knowledge and intellect. By doing so, Reddington further undermines his adversaries’ confidence and consolidates his own position of power.


Law 15: Crush Your Enemy Totally

Reddington is not afraid to use extreme measures to neutralize his enemies. He is ruthless in his pursuit of vengeance and often ensures that those who cross him face severe consequences. Reddington understands that leaving a potential threat alive can be dangerous, so he takes decisive action to eliminate them completely, both personally and through manipulation of others.


Law 16: Use Absence to Increase Respect and Honor

Throughout “The Blacklist,” Reddington strategically employs his absence to control the narrative and manipulate others’ perceptions of him. People are left speculating about his whereabouts and activities, fueling curiosity and elevating his enigmatic status. Yet he always shows up when he’s needed, which links to law 35: Master the Art of Timing.


Law 27: Play on People’s Need to Believe to Create a Cult-like Following

Reddington is a master of persuasion and influence. After all, he has built an empire and is dubbed as the concierge of crime. He knows how to tap into people’s desires and beliefs, manipulating their emotions and motivations to serve his own interests. He often creates a sense of loyalty and admiration among his followers, leading them to believe in his cause and support him unquestioningly.


Law 28: Enter Action with Boldness

Reddington is known for his audacity and willingness to take risks. He often enters high-stakes situations with confidence and a bold approach, which allows him to gain the upper hand. He exudes fearlessness, giving himself an edge over his opponents.


These are just a few examples of how Raymond Reddington from “The Blacklist” applies various laws of power from Robert Greene’s book. Reddington’s character embodies many of the principles laid out in the book, making him a captivating and intriguing figure to watch. It’s hard not to root for such a character because, in Redington’s own words, “Because, like deep-fried butter, I am unhealthy and yet irresistible.”





In my opinion, Raymond “Red” Reddington from Netflix’s “The Blacklist” is a shining example of a masterfully crafted morally gray character. He has become one of my favorite characters because of the captivating depth he possesses. Reddington’s enigmatic nature, combined with his charismatic charm and calculated manipulation, keeps me on the edge of my seat, constantly questioning his motives and wrestling with my own moral compass. It is through characters like Reddington that I truly appreciate the power of storytelling.


As a writer, “The 48 Laws of Power” by Robert Greene became an invaluable resource in my craft, providing me with insights into the intricacies of power dynamics and character development. It has inspired me to explore the shades of gray in my own writing, creating characters that challenge societal norms and provoke thought. I hope to create complex characters with the help of these laws that will draw readers in and make them think. The combination of a well-crafted morally gray character, like Reddington, and the wisdom of “The 48 Laws of Power” has the potential to unlock new dimensions of storytelling, and I am excited to embark on this creative journey.


If you want to see what else I wrote, get insightful book reviews, and a journey into the realms of imagination, be sure to visit my blog. Join me in exploring the magic of words and uncovering hidden literary treasures that will ignite your passion for all things fantastical on Summon Fantasy. You can also connect with me on Twitter, Facebook and Instagram.



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