The Art of the Deal with a Psychopath
How to Negotiate with a Psychopath
A psychopath would rather have nothing than see you have something. If the deal is a win/win, or even if he comes out ahead in the deal, that isn’t enough for the psychopath. You must end up miserable with your end of the deal. This concept is more difficult to understand than you’d imagine because normal people don’t include the look on your face as part of a deal. But to the infantile psychopath, your face is the KEY. For a psychopath, the look on your face is the most meaningful part of the deal and the entire reason why he enters into a negotiation.
Make No Assumptions
In any negotiation, normally we want to reach a compromise so that both parties get closer to what they wanted. It doesn’t work that way with a psychopath. They’ll never let you know what they really want. Instead, they’ll mislead you because they don’t actually play to win. Their end game is to see the look on your face when you lose. This is a very different game from what you expected.
For example, several years ago, I was helping a psychopath market his toy invention. We planned to attend a toy convention and I offered to book the accommodations. Being a savvy shopper, I stacked a few discounts and coupons to get us accommodations at the Hyatt — for much less than the website rates. Later, when he needed airfare to another convention, I again offered to find discount prices even though he didn’t invite me this time. He had invited someone else. I offered to find deals for that person’s ticket as well. He noticed my enthusiasm and said, “You enjoy doing this, don’t you? Forget it, I don’t need help.” Just the fact that I enjoyed helping him, infuriated him. Yes, they want you to help them but it must be done in drudgery and misery. Most especially, you cannot experience the reward of a job well done. Self-esteem is off-limits to anyone in the company of a psychopath.
The Idealization Phase
While in that instance, that particular psychopath simply declined my assistance when he saw how pleased I was to help him, that’s not the most common response. Most of the time, psychopaths will allow you to help them and then punish you severely once they’ve gained from your efforts. Most psychopath victims are familiar with this shocking betrayal – it is the hallmark of a psychopath. Like the women who were killed by the serial killer, Ted Bundy, after they helped him carry his books when he feigned a broken leg, the last thing a victim expects is to be repaid with evil for their good deed. Yet this is exactly the psychopath’s intention and it’s the only thing you can expect. It makes no sense but that’s exactly what a psychopath enjoys most about it: The bewildered look on your face as you try to figure out what you did wrong or wonder what you could’ve done differently. The truth is, with a psychopath, no good deed goes unpunished.
When you help someone, the last thing you would expect is that they resent you for it. But the psychopath sees you glow with satisfaction and wants to wipe that look off your face.
Can the Psychopath Be Useful?
A psychopath’s goal in life is to be of use to nobody. They use people and they don’t want the tables turned on them. On web forums, I’ve read comments suggesting that a psychopath might be of use in certain professions, such as a soldier, surgeon, pilot, or spy. These are roles that require nerves of steel and less empathy. While it may seem that a psychopath is well suited, it doesn’t take into account that they have no sense of loyalty or responsibility. If their role is to drop a bomb on the enemy, they are just as likely to turn it around and drop it on their own team. If they’re supposed to extract a kidney, they’re likely to cut off your leg or your liver too. Betrayal is the one thing you can count on from the psychopath because it’s what they enjoy. If you hire a psychopath to do a job, you can count on them to ruin your business, to leave you responsible for their destruction or just to create the chaos that they’re famous for. They love watching the world fall to pieces around them. Chaos is where they’re most comfortable.
If you find betrayal useful then, yes, you can find a use for them. If you survived you’ll have the opportunity to see your blind spots.
A Psychopath’s Bag of Tricks
So how does a person deal with a psychopath without losing everything? The obvious way is to try to avoid making deals with a psychopath. If you can, present an expressionless face and a lack of dramatic response. Then the psychopath might go looking for greener pastures. On the other hand, if you have a lot to lose, he may see you as a challenging conquest anyway.

In addition to their mask of sanity, the psychopath has another weapon: they know what you want to believe. They know that you want to believe that you can perceive them clearly. To that end, they’ll portray a generally good and likable persona. Usually, that persona will also include some flaws that they’re supposedly working to improve so that you’ll also have compassion for them. They’ll behave rationally long enough to gain your confidence. Although most psychopaths won’t reveal their diagnosis in person, online web forums are full of people who are self-professed ASPD, narcissists, or psychopaths. Some of these people say that they “really care about their spouse or children” and “only hurt people who deserve it.” This keeps naive people believing that they can “deal” with a psychopath without getting hurt because they understand the psychopath’s motivations.
Unfortunately, most people can’t imagine the reality of an emotional vampire’s perspective: They’re hungry and everyone looks like food to them.

To feed, a psychopath needs control of their victim’s reality. They want to control what you feel and consequently, what you believe. In the end, they want you to feel that you don’t know what to believe, what to expect, what’s real and what’s fake, whether you’re hearing and seeing the truth, or being deceived. This is because they have no grounded reality. Their truth is fluid and they want you to join them in that free-floating abyss. Betrayal is a shock that unhinges you from the ability to trust and consequently, that’s the ultimate tool they’ll use to get maximum emotional output from their victims.
If you fail to spot-the-spath, there are still measures you can take to protect yourself. You can take some of the proactive steps that psychopaths take. For example, many psychopaths teach themselves to vomit at will, just in case someone poisons them. They do this because they’ve poisoned other people.
But poison isn’t just for the body, it also applies to the mind. You can protect your mind from the insidious poison of the psychopath by not swallowing anything they tell you. We often assume that something is true because there is no reason to lie. With a psychopath, that just doesn’t apply. They lie when there is no discernible reason. If their lips are moving, they are lying. Whether it’s declarations of love or hate, warnings or threats, double-check everything they say, and ask people who can verify. This is an excellent strategy because pathological lying is another red flag that you’re dealing with a disordered person – very possibly a psychopath.
Buy Insurance
Hedging bets is another strategy they use. The psychopath will buy a stock and also buy the option. Again, this doesn’t have to mean literally, it can also mean that they will be a double agent, or betting against themselves and taking a fall in the ring. So basically it means buying an insurance policy, but not necessarily letting the other party know.
Another strategy they use is to borrow money then set up a loss in business and use it as a write-off. The lender is left holding the bag but the psychopath actually benefits from the loss. We can take a page from the psychopath’s book by getting insurance on any business deal and not investing more than we can afford to lose.
My ex-psychopath told me about a friend who inherited an apartment building. He convinced the friend to sell the building and invest in a recording studio. Ex-psychopath built it, ran it, and lived in it for a few months until it burned down under suspicious circumstances. Luckily for him, Ex-psychopath wasn’t home that day and neither was his most prized possession, his guitar. Now that I know better, I believe that Ex-psychopath just couldn’t bear to see his friend have anything, so he convinced him that they could invest the money in a business and then just burned it to the ground. They had neglected to buy insurance. Again, he wasn’t playing to win, so much as to see his “friend” lose.
Compartmentalize
Since money is not the only thing psychopaths take, insurance is only good for partial protection. Anything you value is at risk: Your family, friends, reputation and health. The psychopath uses compartmentalizing to protect himself from this damage. They keep their relationships separate or even secret. So when they’ve burned one friendship to the ground the other friends don’t get wind of it. Compartmentalizing your relationships is actually a good protection from psychopaths. Before a psychopath destroys their victim, they will turn all the victim’s sources of aid against them. This strategy can actually be turned around and used by the victim as a way to “separate the wheat from the chafe.” We can more easily recognize true friends from false friends when a psychopath is involved.
Ex-psychopath once told me that he had seen people lose everything they owned to a casino. He said that some gamblers would bet their retirement funds, and then lose it all. He said he was sure they walked out and committed suicide. This is the kind of loss that whets a psychopath’s appetite. So when I mentioned that I enjoyed bargain hunting because it’s kind of like gambling, that caught his interest.
“It is?” he asked, intrigued.
“Yeah, it is! Except you always win!” I replied.
“Oh,” was his dejected response. He lost interest and walked away.
Use Your Poker Face When You Play Chess
It’s all about values. The psychopath has no values so he looks to your facial expression to inform him of what’s valuable and he focuses on that. Psychopaths are known for being greedy but that’s only because they want what they think everyone else wants. Money is a safe bet, since our culture has placed a high value on it. They simply want to see the expression of envy on your face when you see that they have more money than you do. This is a method of trading places with their victim – they want to make their victim as envious as they, themselves, feel.
For a psychopath, the “Art of the Deal” begins with hiding his true intention, which is for you to lose. The psychopath’s next move is unpredictable because he really doesn’t care how you lose, just as long as you know that you’ve lost. It may even end with him losing as well, but he doesn’t care, as long as he gets to see the look on your face, as you stare in bewilderment, trying fruitlessly to make sense of his behavior. That’s what a psychopath calls “winning” because he got your attention.

The art of the deal with a psychopath is to play one part chess and 2 parts poker. A poker face is the card that keeps the psychopath off balance. Remember, the psychopath is playing to see you lose but he won’t know if you’ve lost until your face tells him.
It’s no surprise then that the archetypal “devil” in mythology is often portrayed as out looking to make a deal. From the biblical temptation of Jesus to the story of Rumpelstiltskin, we see the devil making promises with ulterior motives.
In my next blog post, I want to take this concept to the next level. I’ve explained how a psychopath steals your money and possessions, your loved ones, and even your self-esteem. In the next article, I want to tell you how the devil steals a soul. I’ll tell you about a devil who stole a young boy’s soul. He traded it for a candy bar.
Skylar, finding your blog 4 years ago was a true balm for me. I had been targeted by psychopaths a couple of times and I think I didn’t fully understand what had happened until I started reading your posts. But the wisdom of your words go far beyond leading with this kind of beings. You’ve made me rethink about human condition. Many thanks for your blog!
On the other hand, as a Mexican, I very much regret the fact that Trump is the American president right now. I’ve read this post keeping on mind what he has done about Latin Americans, and how he has blackmailed Mexican government to cause so much suffering to immigrants. It is so hard at times to keep hope, but re reading some of your posts helps a lot.
Sonia, yes, that’s exactly what this blog is about: the human condition. Psychopaths are extreme forms of certain parts of the human condition and we can see ourselves more clearly because of them. So, despite themselves, they tragically do serve a purpose.
I am very glad that my writing has been of use to you.
As to the political climate, well I hope that this article gets read by all the people who would find it useful.
Hi Skylar,
I am so glad you’re writing again.
hi Skylar, I’m so glad you are posting again, I always enjoy reading your writings. In this current post, it seems you are talking about a moderately intelligent and sadistic psychopath. It seems to me there are different types depending on the level of sadism, intelligence, and also emotional intelligence. They lack empathy entirely, but they vary in their ability to read others’ emotions. For example, my mother cannot read others’ emotions or body language. This causes her to alienate others with her inappropriate laughter or smiles when they are not called for. I have seen her completely oblivious to the fact that other people are reading her body language and know what she is feeling. this allowed me to understand that she cannot read others’ body language. it is like a complete cognitive defect. she would do sadistic things and even told me of crimes she had committed, but I think it was all self serving, like the ends justify the means, or self aggrandizement. Her fits of hysteria were probably calculated to guilt me into something, rather than see a look on my face because I don’t think that meant anything to her. She enjoyed doing things for other people but so that they would be either indebted to her or to build up her sense of superiority. People always get hurt around a psychopath, but it isn’t always because they are intentionally sadistic. My ex was more sadistic than she was, but she actually scores higher on the psychopathy checklist.
My ex understood human emotion and was all about manipulating it in order to get a thrill, whether he was hurting people or making them think he was gods gift. He was definitely sadistic when it came to his scapegoats, but he did not scapegoat everyone. He was very intelligent and knew that his survival and continued ability to torment me depended on the rest of the population believing that he was a good person. so he spent all of his energy acting a part, pretending to be the person everyone wanted him to be, while when no one was looking he would threaten me, or do things to my children that he could get away with, just in order to hurt me. His favorite mantra was “love and compassion”, and they went on about this at his memorial service, while I was gagging in the bathroom, knowing he had molested my son. This goes back to your 180 rule. I tried the poker face, just instinctively, but he knew he could always use my children against me. He did this up until a few weeks before he died of thyroid cancer with metastases in his brain. Now his mother hates me because all she saw was my reaction to his behavior, and she won’t see us, her own grandchildren, because I was “mean” to her son. I continue to protect her from the knowledge of what he really did: there doesn’t seem to be a point to vindicating myself and his apple didn’t fall far from her tree so I’m not going to look a gift horse in the mouth and keep trying to see her. Anyway, there is no explanation for him to keep doing what he was doing when he knew he was going to die soon, other than that sadism, and lack of concern for his son’s welfare. My son was suicidal at age 8 and my ex kept vetoing my ideas to help our child. But despite the fact he was sadistic, my point is that the more intelligent the psychopath, the more their attempts to remain hidden will limit what they are willing to do because they don’t want to risk exposure. So while their lack of empathy makes them relatively predictable, there are still variations in they type of spaths they are, depending on the extent of cognitive damage and the degree of intelligence. I kept worrying that at his end he would do something dramatic and kill us all in order to hurt me, but his motivation to remain the hero in everyone’s eyes after his death was stronger than that.
I think there is a wide variation in them, and I am still trying to figure this out. My kids’ middle school principal just outed himself by gaslighting my daughter and victim blaming her for no reason. Now I am unable to take him seriously, and I have the superintendent telling me that I have to work it out and deal with him. He wants to have a meeting where I hash out my differences with this principal. The last thing I will do is invite interaction with these people, it just gives them more opportunity to flagellate their egos and manipulate others. but I am stuck because no one around me will understand me explaining that he manifested spath tells. This guy is acting all the time, his personality is sort of larger than life, but he is very minor league. He is mainly about playing a role to hide what he really is, just to get by, and the tells come out because he just can’t hide himself perfectly, not because he is necessarily doing these things on purpose to be sadistic. he’s just a flailing idiot. I think many spaths are in this category, not really sadistic but just out of their depth in an empathic society and trying to pretend they really know what is going on. In some ways I feel sorry for them. It’s like a learning disorder or mental defect that they are terrified of people finding out.
Hi Mnav,
I’m not referring necessarily to someone with any intelligence, it’s just the nature of the psychopath to feel better when other people are sad. They feel less alone. But as Sonia noted, observing the psychopath teaches us about human nature. Psychopaths are not the only ones who like to see others suffer, when “normal” people feel this way we have other words for it, “schadenfreude” is one such word. Other times, I’ve heard people comfort themselves by saying, “well at least I’m not…, like __(fill in the blank).
Also, many people inadvertently make others feel bad due to bad social skills. I often walk around with my foot in my mouth. Nothing new there.
The difference between normal people and psychopaths is the extreme to which they take their sadism. They would literally rather have nothing than see someone else have anything.
I suppose that’s why the Narcissistic Personality Disorders are considered a “spectrum” of disorders. We all have some infantile behaviors in us at different times, in different situations, but the psychopaths are at the level of a fetus and it’s all the time. YET, they hide it with a mask. That’s a very important part of the equation because this is how they’re able to feed on their victims. Generally, the more intelligent they are the better the mask, but that doesn’t make them less infantile.
hi Skylar;
yes, I agree. And I think the very fact that the psychopath hides what they really are, is evidence that they know better than to act this way and that they are fully responsible for their actions. see this article on Yahoo which is a joke:
https://www.yahoo.com/lifestyle/know-calling-abusive-person-narcissistic-162040122.html
and yes everything is along a spectrum. I have noticed narcissistic behaviors come out when a person has suffered some sort of brain damage, as if it is a primitive function of the brain. In these cases, the person doesn’t try to hide it because they just think they are entitled to act this way.
I don’t think that I enjoy the idea of anyone suffering, but I think I do get a sort of sense of justice if a psychopath suffers. After the things they do, they seem to deserve it, and when one never suffers for what they have done, it seems wrong. It’s more along the lines of karma, rather than feeling joy at others’ suffering. Maybe this is a sense of comfort that the world is unfolding as it should. When my ex died, I just felt intense relief that we would finally be safe. What will we feel in January 2021?
Hi Mnav,
that article is classic narcissist. They have no concern for the victims, only concern for the abuser. It’s typical role reversal, like the judge who chastised the rape victim for ruining her rapist’s life by reporting him.
It’s true that psychopaths with brain injuries don’t hide their entitled attitude as well as you’d expect, but really, they just change the recipe: they use more pity ploy to get away with their abuse.
Here’s an example: a developmentally disabled man was dropped off at the community pool by his caregivers. He’s well known there since he went there weekly for years. I was in the sauna, as were several men, when he walked in and boisterously greeted everyone. Nobody responded much and he left after a couple of minutes. People walked in and out every few minutes, since it was very hot. A while later I left.
When I walked back in about a half hour later, he was the only one sitting there. Then he propositioned me, in some very vulgar terms.
I walked out and reported him. The lifeguard tried excusing him due to his very obvious mental disability. But I pointed out that he waited until there was nobody else around, so he knew how to keep the mask on. I spoke with other staff and they also initially tried to excuse him but when I, again, pointed out that he waited for nobody else to hear him, the saw him in a new light. Then I found out that he had done some other offensive things before. Each time, people tried to excuse him because of his very obvious disability. This is a family center, so this time, he was banned.
Granted, his mask wasn’t great, but he knew that, so he added extra helpings of “pity me” to cover his offensiveness.
That’s how they work. It’s like a recipe. The mask consists of charm, pity and rage, but they tailor it to fit the circumstances. It really becomes surreal when they switch from being disabled to suddenly being very capable. Like Ted Bundy.
hi Skylar;
maybe you can do a piece on how wealth enables these people.
https://www.dailykos.com/stories/2019/8/1/1875937/-So-Jeffrey-Epstein-wanted-to-freeze-his-penis?detail=emaildkre
Hi Mnav,
there was another article where he was quoted as saying that he “collects people”. That is the ultimate psychopathic behavior. He can’t see the difference between people and objects.
Hi WindHorse, I wish I could write more often, there is still more to reveal about the nature of narcissism. Right now, I’m just so busy with so many deadlines, that I can’t find the time.
Thanks for the encouragement though. It does mean a lot to me.
This is brilliant. Another take is political ponorology which explains how they gain power and infect society with their sadism and crazy making. Written by a polish guy after WW2. I’ve read a few posts now and the only thing I disagree with is the idea they have a suppressed shame. It’s simple right hemisphere dominance or inability to process messages coming from the left. It’s a neurological disorder. Iain McGilchrist has written a book ‘the matter with things’ and documentary, the divided brain. It’s not psychological, it’s neurological and can be advantageous in certain contexts, can be compared to autism where you’ve got very high functioning savants through to non-verbal. Funny thing about women though. So many people on these sites have had a narcissistic or borderline mother, many more than father, yet statistically women are a minuscule proportion of the cluster b or psychopath. Our brains are different, we have greater connections between hemispheres, more plasticity and heightened emotional empathy following childbirth. My mother was a cold uncaring cow too, but I think it’s something different. That is more likely shame, inter generational trauma and imprinting.