Looking for The Red Line
How to Ask Your Friends if There Even Is One.
It’s always been good policy to keep your politics out of conversation with friends and family who don’t share them.
But when politics beget untenable national policies—when they cause actual hurtful outcomes—it’s harder to ignore the topics and more tempting to ignore the people, instead.
This unspoken social reshuffling is tough for those who’ve formed strong bonds with a plurality of friends and those whose families harbor deep divisions of political perspective.
“Brother against brother” is an all-American theme still close enough to memory to make us pause before stepping full outside each others’ circles.
I’ve been struggling with this problem since 2020, at least, and more acutely for the past four months. As someone who values friendship and aspires to integrity, it’s increasingly hard for me to hold both goals and be one person.
Part of my effort to address this is to engage with friends not exactly in my line of thought but close enough to make the effort easier.
The harder conversations will come later. There’s no avoiding them.
“J” is a young person of integrity and bright intellect, who was raised in America’s unapologetic, conservative heartland by people, and among people, who bear that distinction with pride.
I quizzed him earlier this week about Trump, and he puzzled at my assumptions about his view, which were in fact incorrect. He opposes Trump, but his thoughts were more nuanced (no surprise there), and he challenged me to consider whether some in Trump’s orbit were maybe harboring a notion of the greater good; and could I not at least acknowledge that.
I cannot. And so, I put the question back to “J.” in the following text exchange I’m reprinting here with his permission.
(I also had his permission to use his full name, but since we have mutual friends, and he’s young enough to recant his views, I’ll just call him “J.”)
I post our chat here to share with Future Me and whomever else might benefit.
Matt: What would be a red line for you, J., in finding categorical objection to Trump’s actions as President?
Assuming you haven’t reached that. Maybe you have. If so, what was it?
J: Define “categorical objection.” You mean just to object to his actions?
Matt: No. I mean a default position, whereby in your view, he’s proved himself an illegitimate American president, irrespective of any particular action. When he has disqualified himself, categorically, from a position of public trust.
J: [He has] from the very beginning. From 2016. Trump University was enough for me. The way he approaches topics, the way he lies, the populism. That was all enough for me to vote for anyone but him.
As far as actual actions as President: Withholding aid to Ukraine in an obvious quid pro quo; contesting the 2020 election and inciting a riot in the wake of it. Priming his base to think the election would be stolen, knowing how many mail-in votes were sent in and knowing votes are counted last in first. All of that stuff he did.
The list goes on for me, especially this time around. Don’t even get me started on the meme coin [Note: J. is a financial advisor]. I thought I’ve been clear that I think Trump is a bad option, and no one dislikes him and what he stands for more than me.
Just because I’ve been less certain that American democracy is inevitably over, or the fact that I’m interested in underlying incentives [and] what people truly believe; or that I take a nuanced view on why half of America could have possibly voted for him, doesn’t take away from this.
I think underpinning everything I think and do is a revulsion to certainty. I see certainty as the root of so much trouble. People being uncomfortable with just not knowing things underlies much of what’s wrong with the right, especially conspiracy thinking, and it also is behind a lot of what went wrong on the left to push so much of America, so many two time Obama voters to Trump.
Maybe me disagreeing with you has made it seem like I am undecided about who Trump is and whether he is good for this country, but I am not undecided. I just have a habit for finding the most interesting conversation in disagreement. There are so few things we disagree on, but I think one of them is in your certainty about the direction America is headed.
(One thing about being “uncertain,” at some point you will inevitably be too slow to act, too slow to stand up. There is great danger in that as well. I am aware of it.)
Matt: I should have framed my question better. Clearly we agree about Trump.
J: Oh, sorry. lol.
Matt: No, it’s ok. I’m trying to find ways to understand this.
I don’t see Trump as a singular threat, although I believe he is clearly a threatening figure.
I believe he’s become, rather, a figurehead for a coalition of bad actors, specifically: anti-democratic, far-right authoritarians (fascists); oligarchs; white nationalists; Christian fundamentalists and conservative culture warriors; techno-imperialists; conspiracy theorists. A wide range of perspectives that have plenty of historical representation but not, in my view, positive ones.
I believe this coalition represents specific objectives the U.S. Constitution was framed to counter or impede. I believe America’s framers were aware of these elements, if not precisely as they may appear today. I believe other democratic countries see things similarly, which explains much of the post-WWII Western alliance.
It is notable (and to the point) that this alliance is specifically targeted by the current administration. It stands perfectly to reason.
I believe an authoritarian regime is recognizable by its words and actions. I believe it behaves consistently and repeats necessary themes.
That’s the largest banner I would use to signify the coalition that Trump’s own criminal instincts and behaviors have attracted.
So, in framing it that way, I guess my question is: “Why, if Trump’s authoritarian aspirations and behaviors are objectionable to you, would you not categorically object to his enablers and lieutenants as well?”
Or in other words, how far would you say one needs to extend the benefit of doubt to be fair to those who support Trump and Trumpism?
J: Ahh yes, a much better question.
Matt: I don’t mean it rhetorically. Am trying to answer it for myself
J: I think many people supporting Trump, especially at the ground level, do so out of fear and objection to what they see as a morally vacuous, authoritarian, and conspiracy riddled Democratic Party [which is] both godless and religiously dogmatic in a woke ideology. What they see as going against everything this country has represented. They are willing to do anything to stop this.
Now, I personally think that the Left went off the deep end for a little while in the 2010s and early 2020s. There has been a big course correction, not perfect, but it’s gotten better. Despite this, it has been blown out of proportion by people on the Right, especially during Covid; and if you combine social media algorithms with constant coverage of wacky stuff on the Left, you can understand how people who don’t see things in perspective, who . . . watch sensationalized coverage and algorithmic clips, could start to see this as a bigger problem, one that takes drastic measures to fix.
This allows for a constant “what-about-ism,” where anything you say about Trump will be what-abouted justifiably in their minds, truly and in good faith. It’s not because they’re all a bunch of racist bigots, but because they are terribly misled.
This is my view.
How far this [characterization] extends to the higher-ups, I don’t know. But I think it’s always better to believe that what people say they think is truly what they think, because nothing breaks down discourse quicker than misrepresenting someone’s views. It makes us look dishonest, not them.
You can still fight just as hard against those views I believe. Against the policies.
Matt: Thanks for that. You’re not the first to tell me about the perceived tyranny of the Left by regular folks on the ground. I have tried to be sympathetic at the individual level—especially and critically with regard to friends who are still voicing their support for MAGA—but it’s getting extremely hard for me to understand how, cultural differences aside, we cannot agree on defining common ideas like: criminality, greed, ineptitude, cruelty, dishonestly, bad faith, even fairness as a settled concept.
I’m struggling to find the place–ratcheting back to what I once thought were core American principles–where we can agree.
Even “agreeing to disagree” seems dangerous to me now, simply by extrapolating the end games of our different views. The path we’re on is a dissolution of America as defined by its own plain language reading of the original documents. It is the creation of a different country.
I don’t know where to go with that, because the country our direction points to is not one I would recommend to anyone I care about.
I’m facing quite a challenge with this. And it alarms me further that this extrapolation seems far fetched to so many I talk to.
J: It’s all very troubling for me too.
It’s not as clear for me to know when it’s time to panic and when it’s time to see things in perspective, through the lens of history, and realize that polarization ebbs and flows in a country, that trends rise and fall.
That we have fought a civil war before and came out the other side of things like Jim Crow and the [Civil Rights Movement].
I view us in a backsliding democracy, not a failed one. Not yet. But I do know, without a doubt, that we are closer to failure, to a real break, than we’ve been in a long long time.
I think much depends on what happens after Trump, if things settle down.



Fighting the good fight, Matt, one person at a time. How far is too far is definitely the question people need to be addressing. Yes, where is the line. That people see that line as mutable, is disturbing.
Great piece.