Here’s How I Tricked Another Trump Supporter Into Admitting He’s a Wannabe Dictator and Con Man

This is about the third or fourth one of these articles I’ve written where I’ve gone over a debate I’ve had with a Donald Trump supporter. I hope that by sharing some of the tactics I’ve found to be more effective, they might get used by others who take on the mind-numbing task of trying to reason with and/or debate these people.



Eventually this latest discussion spiraled into talk about authoritarian dictatorships, where I pivoted toward North Korea as a prime example of a strictly controlled population that’s been fed, since birth, propaganda by rulers who dictate the behavior and access to information of the people living there. I even used Saudi Arabia and China as other examples of leadership styles that, while not dictatorships (China is communist while Saudi Arabia is a monarchy), still highly censor and restrict the freedoms their citizens have.

Naturally, we both agreed that these nations, while different in many regards, all shared the same heavily restrictive nature over the freedoms of their citizens. My friend agreed that it’s vitally important for these nations to be brutally controlling when it comes to freedom of expression or information, in order to maintain their control. Though I had to make sure to skate very easily around this to avoid him picking up on the trap I was setting.

Then I brought up Adolf Hitler. We discussed how he effectively used fear and nationalism to manipulate people into believing horrific things that weren’t only inhumane, but also completely untrue and against their own interests. I stated that fear is a wonderful form of manipulation considering someone who’s afraid will believe all sorts of illogical things — and he agreed.

That’s when I shifted the argument into a more philosophical tone. I mentioned how Nazi Germany, the Saudi Arabian monarchy, the North Korean dictatorship, and communist China are all technically different forms of government, yet they all share many of the same traits. It was around this time where I said that, in many ways, these types of authoritarian leaders are really just extremely elaborate examples of con artists who use their power to carry out incredibly intricate scams to fool their people into believing outright lies and propaganda.

My pro-Trump friend also agreed with that assessment.

Successfully clearing that hurdle, I continued the philosophical debate linking con artists and dictators, more specifically the traits they all must share to be effective. That’s when I began to rundown a list, asking my friend if he agreed with each question. Do these oppressive regimes:

  • Rely heavily on controlling the information their citizens receive to create the illusion of something that’s not real? He agreed.
  • View a free and open press as a friend or an enemy? He said they obviously oppose freedom of the press since none of those nations have it.
  • Promotion nationalism as a way to build morale among their citizens to distract them from the truth? He agreed they all did.
  • Push the idea that they are the only people who can be trusted, while vilifying any critics of their rule as the enemy? He agreed.
  • Try to intimidate or eliminate anyone or anything that threatened their position of power? He agreed with that, too.
  • View any criticism, especially truthful criticism, as an attack on their power? Once again, he agreed.
  • Support conspiracies to justify their propaganda against enemies, like how North Korea does with the United States? This one he said he wasn’t sure, but sounds about right.
  • Will always play the victim when things aren’t going their way by vilifying a group of people, another nation, or something other than themselves for failure? Again, he agreed.

That’s when I asked him the question I had been building up to: So you would agree that many of the tell-tale signs of an oppressive dictatorship led by an authoritarian tyrant would include leaders who often play the victim to justify failure; view freedom of the press as the enemy; use nationalism to manipulate their citizens; use threats or intimidation to try to silence critics; view any criticism of their policies as an attack on their power; often push conspiracies to justify their propaganda; and perpetuate the idea that they’re the only ones who their people can trust and anyone contradicting what they say are liars trying to undermine the greatness of their leadership?

“Yeah, that sounds about right,” he said.

“Well, congratulations, you just agreed that Donald Trump acts and behaves like a con man and a dictator,” I replied.



I wish I would have taken a picture of the look on his face. It was a mixture of the proverbial “deer in the headlights” and panic trying to find some way to respond after realizing I had just lured him into this trap.

First he tried to deny Trump had done any of that, using the typical spin many of his supporters use. I went through everything I had mentioned, pointing out examples where Trump had perfectly displayed those traits:

  • Wanted to control the information citizens receive to create an illusion of something that’s not real: His frequent attacks on the media, even pushing the ridiculous claim that they’re not reporting on terrorist attacks — aka creating something that’s not real.
  • View a free and open press as the enemy: Donald Trump called the media “the enemy” on Twitter.
  • Promotes nationalism: His slogan “Make America Great Again” is textbook nationalistic b.s. and he’s often used “rebuilding the military” (even though our defense budget has remained in the hundreds of billions of dollars for years) as a way to push this idea that we’re weak and no longer great — but he’s going to fix all of that.
  • Push the idea that they are the only people who can be trusted while vilifying critics: Again, constantly attacking any negative media about him as “fake,” while projecting this idea that he’s 100 percent honest and “just telling it like it is.” I even pulled out my phone and showed him the article I wrote where, based on Trump’s own “logic,” Fox News — a source he never calls fake — would, in fact, be considered “fake.”
  • Tries to use intimidation against critics who threaten his power: Again, his constant attacks on the press, plus his lashing out at people or businesses on Twitter who dared to speak out against him. Even his behavior as a businessman, often threatening lengthy lawsuits out of spite, was his way to try to silence people who might go up against him.
  • View any criticism as an attack on their power: I asked my friend to name one instance where Trump admitted he was wrong and took full ownership of it — he couldn’t name a single thing.
  • Supports conspiracies: I brought up his 9/11 conspiracy and his “millions of illegal votes” costing him the popular vote for which he’s yet to provide a single shred of evidence. I then asked my friend if he could and, once again, he could not.
  • Always plays the victim when things aren’t going their way, blaming others for failure: I went back to his whining about The Apprentice not winning an Emmy to prove that Trump has a long… long history of claiming things are “rigged against him” or citing conspiracies whenever things aren’t going his way.

I even brought up how many dictators want huge displays of “admiration” for them by way of public events where people show up to cheer their every word. You know, kind of like what Trump loves, holding events where his fans show up to feed his own ego while they cheer his every word.

Naturally, my friend tried to argue some of those points, resisting the overwhelming facts I had just used to prove that he agreed that Trump’s behavior is very much like a dictator. I reinforced that he couldn’t agree authoritarian dictators share all of these traits, but then deny that Trump behaves like one when I was actually describing his behavior when I was running down my list of questions with which he agreed.

That’s when I asked him one final question: If a con man was going to try to fool you into believing a very elaborate scam that obviously favored them but went against your own best interests, would they:

  • Want you to be well-informed with access to factual information and sources that might prove the lies and information they’re telling you aren’t real? — or — 
  • Tell you that anyone calling them a con man is a liar, even possibly jealous, and that they’re the only person you should trust because they’re the only one telling you the truth?

“The second one, obviously,” he said.

“Exactly,” I quickly countered.

This was when my friend, clearly frustrated and flustered, decided to end the conversation and change the subject. He never fully agreed that Donald Trump was a con man who acted like a dictator, but he did agree that my descriptions of both — when I was actually describing Trump — matched the signs of a con man and dictator. The fact that my friend, someone who’s notorious for never giving up in a debate, abruptly ended this discussion was all the proof I needed that, deep down, he knew I was right.

Unfortunately, like many Trump supporters, the truth about the person they support isn’t something they want to face.

Hit me up on Twitter or Facebook and let me know your thoughts.




Allen Clifton

Allen Clifton is a native Texan who now lives in the Austin area. He has a degree in Political Science from Sam Houston State University. Allen is a co-founder of Forward Progressives and creator of the popular Right Off A Cliff column and Facebook page. Be sure to follow Allen on Twitter and Facebook, and subscribe to his channel on YouTube as well.

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  • Cschafe

    And way to kill another person’s hope. I get that you are right. I get that Trump is horrible and has done all, and more, of what you said. But you are so focused on winning the argument and taking down this man’s ideas you don’t realize you killed his hope. The trump supporters hope trump can make a difference for them and that is real. That is needed and that is good. We all know it won’t happen but I actually feel bad for those people that are so desperate they turn to this guy for help. They feel the con of decades of political BS and are sick of it. That is real as well.

    • menotq

      Wow, such huge compassion, while commendable I’d ask the question risks versus benefits. I’ll take squashing an individual hope over policies that could harm millions of humans around the world any day!

      • bobn2010

        But the key point is that arguments DON’T change people’s minds. And that must be the goal. We need to win back votes in order to advance a progressive agenda in the US, and studies have shown that confrontation and fact-based arguments don’t achieve that. In fact, they often polarize and strengthen the opposition.

    • HairyEyedWordBombThrower

      Misplaced hope prevents taking what could be effective action, so your disapproval is likewise misplaced, at least if one is going to treat the person as an adult with the right to make up their own mind.

  • jane hendricks

    Thanks for trying, Allen.Sadly most of them don’t have the attention span to follow your logic.

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  • Sheila Dockins

    Great article, You are so right. Thank you for your insight.

  • anniesmac

    I find it difficult to think that any Trump supporter had an attention span that long and wasn’t completely lost after your first two or three sentences. After all, they respond to disjointed sentence fragments with gusto.

  • Max Mack

    With the ignorant, uninformed, dullard, it does not matter what the truth is. It is only with they belive is true that counts! Facts, Sciencexotic does not resonate with the weak-minded who are easily fooled by manipulative psychopaths. Trump being a weak example. But many low minded Americans suckle up to he teat of sycophantic despots.