Here’s the Question I Asked a Trump Supporter That Actually Changed Their View of Him

I like to think that I’m usually fairly well prepared whenever I go into any sort of political discussion (especially with a Republican), but I’m willing to admit that occasionally I discover some of my most effective methods of debate during these interactions.



For example, yesterday when a Trump-supporting friend of mine who had done their best to avoid talking politics with me actually broke down and asked me what it was about him that I found so objectionable.

The first thought I had was, Where do I even begin

Obviously I brought up his belittling of POWs, mocking of a man with disabilities, his non-stop lying, his childish behavior on Twitter, and the video of him admitting to being a sexual predator. As expected, these were all spun and twisted by my friend who fed me the usual Fox News talking points we’ve all heard his supporters use to defend his vile behavior:

  • He was attacking McCain, not POWs.
  • He didn’t mock a man with disabilities, he’s done that before.
  • He’s not a liar, that’s just what the media wants you to think.
  • I don’t care about how he acts on Twitter, it’s just social media.
  • That was “locker room guy talk” and he didn’t mean it.

Then I remembered my friend had been looking to buy a house and was seeking out a new financial advisor for their retirement and kid’s education since their previous one retired and they weren’t too fond of who replaced them.

So, I asked them this:

If I said I knew a finance guy who promised me that he was brilliant and successful but had filed for multiple bankruptcies; thought it was a great idea to start a mortgage company in 2006; had a long list of failed businesses; accepted a settlement with the Department of Justice after his company was caught racially discriminating against minorities; settled a fraud lawsuit for $25 million after he was sued by former students of a fake university he created to scam people out of thousands; was found guilty of creating a fake anti-gambling organization that used blatant racism against Native Americans in an effort to prevent a tribe from building a competing business; continually lied about why he won’t show his tax returns to prove he’s being honest about his supposed “success”‘; and has been taken to court at least 3,500 times — would you take a risk and put your family’s financial future in that person’s hands?

Their face was blank. Obviously they knew I was describing Trump, but it was also sinking in that there was no way in hell they’d trust someone with all of that on their resume to help them plan their financial future.


Finally, after a few seconds of silence, they simply said, “No, I wouldn’t.”

At which point I said, “Then why do you think a person with flaws like those — and many others — should be in charge of the country?”

“Well, I had never thought about it like that,” they replied.

They tried, but couldn’t spin it enough to mount a solid defense they felt would be valid. They dismissed the fraud lawsuit as Trump just trying to move on so he could focus on “being president” and said they didn’t think it was a big deal he hadn’t shown his taxes. Nevertheless, they agreed that they wouldn’t trust a financial expert who lied about why they wouldn’t prove something that they had repeatedly bragged about.

Did my friend completely turn on Trump? No.

However, they did admit that after thinking about the question I asked them, the way they viewed him wasn’t the same. Then they fell back on the line I’ve heard from many Trump supporters: “Well, he’s president, so we have to give him a chance and see what he can do.”

Would this method work on everyone who supports him? Obviously not. Even though this was a friend of mine, I still had to go item by item to prove each and every incident I cited in my question was true. Plus my friend isn’t as extreme as many I’ve encountered.

In my opinion, I think what made this effective was putting the type of person Trump is to a real-life situation for them. It’s easy for a lot of these straight, white, Christian supporters of Trump to ignore how truly awful he is. But when you make them think about a real-life situation that would directly impact them, that’s an entirely different situation.

That’s why Republicans are clearly terrified to repeal Obamacare out of fear of the backlash they’d experience as millions of their voters would have their health care ripped away from them.

So, for those of you who might take on the mind-numbing task of trying to reason with a Trump supporter, might I suggest a tactic such as this. It might not always work, but this was one of the rare moments where I actually got a Trump supporter to admit that their perception of him was changed based on how I shaped my argument.

Feel free to hit me up on Twitter or Facebook and let me know what you think.




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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