Trump and the 2020 Election: Various Considerations

I really do not want to spend the next four weeks fighting with friends about Trump, so I am writing this article to just articulate what I believe, and what I don’t believe, and what I am doing, and what I am not doing. And then I really plan to just shut up until the election is over (and perhaps this entire four year escapade). I know only one thing with certainty at this time – at such point that the 2020 election results are known, I, and my like-minded conservative brethren, have a lot of work to do. I don’t know the exact nature of that work yet, because the election results are not yet fully clear and the eventual outcome will direct or re-direct what goals lie in front of us. But regardless of who wins, (a) there is a lot of work to do for patriotic conservatives, and (b) that work will not be in vain.

I am not of the opinion that the fate of Trumpism and Trump in particular represents a huge burden for the fate of conservatism, per se. I do, however, accept that the Republican party itself has a lot of work to do, regardless of the outcome of the election, if it is to (a) Seek to win elections in the future (it probably ought to hold on to that little goal), and (b) Maintain its status as the party of conservatives. The divisions, the splits, the personalities, the priorities, the strategies – all the unpacking and re-packing that lies ahead – all of it is on hold until there is election clarity. But again, all of that is a matter for the partynot the philosophy that is movement conservatism. I don’t share the fear of some of my friends for the future of ideas, because great ideas transcend the transactional and the temporal.  The idea that is conservatism, enshrined in the principles of our founding, is not movable.

I am sure much of what can and should be said about the path forward for both Republicans and the conservative movement will be said after the election. I hope to play a part in that conversation and I have strong feelings about what is needed to solidify relevance, influence, and principle post-election. But for now, the question on everyone’s mind is much less strategic, much less tactical, and much less ideological. For now, it is merely this – Do you support Trump or not?

I did not vote for Trump in 2016 and I wrote many times in 2015 and 2016 why that was. I wrongly believed he could not win, and did not believe there was a reason to support a man who so clearly stood against so many things that mattered to me. I wrote then that if I were in Ohio or Florida and the issue was just “who would you rather have – Hillary or Trump?” – I would vote for Trump. But I voted in California in 2016 so had the luxury of not needing my particular vote to come down to a lesser of two evils dilemma. However, I should be clear – I affirm the reality of lesser of two evil voting, and do not begrudge the thought process that goes into such, at least in this setup thus far.

I have spent the last four years trying my very best to call balls and strikes. I vehemently disagree with the way the left and the Trump-deranged have attacked his Presidency, not only because I consider it uncivil, anti-intellectual, and undemocratic, but also because I believe it created the opposite result of what they would say they were after. Put differently, I believe Trump responds to very little more than flattery, and those who claim to have wanted a certain policy activity from POTUS would have pretty much gotten it had they taken a different approach. The response to Trump’s shocking victory over the corrupt and intolerable Hilary Clinton was to do the very thing they have accused him of – undermining institutions, norms, and truth at every turn. We all are worse off for it.  The “resistance,” broadly speaking, is unprincipled, undemocratic, and shameful in their demeanor and tactics.

I am well aware of what the President has done to invite this behavior, and I simply have no interest in continuing to play this never-ending game of chicken or egg. When one is stuck in a negative feedback loop of unacceptable behavior, someone has to break the chain. I know of no way to navigate the moral relativism and disdain for norms embedded in our current political discourse than to buck the trend – to refuse to play along – to call a spade and spade, and try my very best to be decent and civil in my interactions. Where I have failed in this commitment, I apologize. But I have earnestly tried, and I believe that President Trump has produced a non-stop endeavor at praise/criticism ping-pong.

I can make a list of Trumpian policy achievements where I am sympathetic.  It is a substantial list. I favor a more competitive corporate tax code. The embassy in Israel belonged in Jerusalem. The federal judges he appointed are, to a man and woman, splendid. The deregulatory efforts in the economy have been wise and needed (and fruitful). The cabinet efforts at DOE and HHS to advocate for due process and for the life of the unborn (respectively) have been stellar. As you will see in two paragraphs, I may not support the tactic of tariffs to deal with the Chinese, but I absolutely believe that someone needed to quit pretending the CCP was an ally of the United States, and address the danger to national security that so much of our relationship with China entailed and entails. Leaving the Paris Accord was the right thing to do, as was leaving the foolish Obama-Iran deal. There has been very little legislation passed the last four years, but that is true of the Obama presidency as well, and it is the reality of divided government (though in this case, the divided government is largely a by-product of the debacle of a 2018 midterm).

There is also a list of Trumpian policy where I am not at all sympathetic. He is nothing close to a fiscal conservative, and those fiscal conservatives who chewed Bush Jr. up and down over spending but have turned a blind eye to Trump should be ashamed of themselves. The shame of the Cares Act’s $2.2 trillion is, believe it or not, not its’ cost; it is the $1 trillion+ deficits we were running before there was such thing as a COVID crisis. His tariffs have done great harm to American importers and farmers. His heavy use of executive orders is shameful, as is any attempt imperialize the Presidency. He has not done anything with infrastructure (thank God), but has continually threatened to launch a trillion dollar crony-capitalist boondoggle. His foreign policy has been mostly incoherent, with shameful kissey face moments with dictators and despots, but a firm and effective response to ISIS, and on-again/off-again rhetoric about the threat of Jihadism vs. silly rhetoric about American intervention.

I think there are areas in which he deserves an A+ (judges and life), a B (taxes), a C (China), a D (foreign policy), and an F (spending). That, my friends, is not a 4.0 GPA – it is about a 2.5. Better than Obama. Better than Hilary. Better than Biden. But in policy only, a 2.5, not a 4.0.

But the policy aspect of Trump – which is good and bad – is not the entirety of his portfolio. There is, next, his personnel, and finally, there is, well, him.

With personnel, Gary Cohn did a fine job as head of the National Economic Council, and his replacement with Larry Kudlow was brilliant. Kevin Hassett at CEA provided more free market heft in national economic policy. Betsy DeVos as Secretary of Education has been nothing short of spectacular. I believe the country is better off with Mnuchin at Treasury than we likely realize. Pompeo has served us well at State. Bill Barr is a national treasure at AG, and his haters know not of what they speak. There have been some excellent and crucial picks in the administration.

But there have been disasters as well, and I mean, face-in-palm mind-numbing disasters. Not a few – a lot.  Some of these are labeled disasters by Trump himself, never seeming to realize he was the one who selected them. Others need not even be addressed – left, right, and middle are equally shamed by their having been in the administration (I’ll start with Omarosa and let you take it from there). The mind-numbing turnover and constant palace intrigue is the biggest counter-argument one could even imagine towards the idea of a “businessman” serving as President. The notion was always supposed to be, “government is incompetent; I am a private sector success; let me come in and get it right.” Well, if Human Resources were a vital part of private sector success, this experiment did not go well.

Then we are left with Trump the person in my three-prong analysis (policy, personnel, person). I will divide this up into two categories: the principled, and the pragmatic. As a matter of principle, President Trump has one governing principle – the same one that has governed his every move since the beginning of his adult life: how does it feed his ego. His never-ending insecurities and thinner-than-wafer skin are not mere personality defects, they are the over-arching composition of his identity. I do not say this to troll him, to dunk on him, to play armchair shrink with him – I say it the way I would observe that a car just passed me by – it just is. And in this case, it is the reason I believe he is about to lose the election in a bad way (the pragmatic). I have grave concerns with one who spent three decades seeking to avoid business and marital commitments, but once that person was elected, perhaps I could grapple with the complexity of one’s lifetime moral deficiencies towards a potential greater end. But how can I do that if the very behavior and temperament I am talking about keep that person from staying in office long enough to do all the things I am told are so important for the betterment of the country? In other words, why is it the fault of those annoyed by boorish and crude and childish and stunningly unpresidential behavior and not the person who is, ummmm, President of the United States?

If there is one thing I hear more than anything else from those confused by my [fair and warranted] criticisms of President Trump, it is that the desperation of the times calls for “movement” people like me to press pause on my fetishes for norms and manners, and just accept that the Supreme Court, lawlessness in the cities, cancel culture, and other sorts of truly desperate situations trump all of the unpleasantries of the President and his tweets. And indeed, we are living in serious times. And the stakes in our culture are high right now. And Joe Biden, Kamala Harris, and the Democratic Left have a vision for America right now that is self-evidently disastrous, and should be resisted and stopped at all costs.

And yet, I remain incredibly confused by the logic of this construction. “The times we are in are so severe that you must ignore A, B, and C behaviors from the President, but the times are not so severe that the President must refrain from behaviors A, B, and C.”

With everything I have said above, you may conclude that my criticisms of some policy, some personnel, and some personal character, that I would not vote for him. But the fact of the matter is that if I lived in a battleground state, I could and I likely would. Some of my dear conservative friends disagree with me here, and that is okay. And this is sort of the bottom line of my whole article. It is time we have a little empathy for those who feel they must vote for Trump, considering the alternative; and it is time some of you have a little empathy for those who feel they can’t vote for Trump, considering … There is ample prima facie support for both positions where just the tiniest amount of grace and understanding are present. After the election I will write substantially more about this, but the most impassioned among us are not ready to hear it yet. All I can say is I understand why a conservative would not vote for him, and I understand why one would. I do not believe either conclusion can be called wrong in the spectrum of options available to a thoughtful voter.

But I would have 100x more understanding of the pro-Trump voter if it was accompanied by skepticism, criticism, and eye rolls. What I learned the last four years is that “the lesser of two evils” does not stay there; once one says, “he’s better than Hilary,” it is an inevitable slope towards defending the indefensible. And I want to publicly say that President Trump has never done anything in his life or presidency that has grieved me as much as seeing conservatives defend what they know cannot be defended – all from a starting point of, “he’s better than Hilary.” They are right, by the way – the country is better off with his petulance and incompetence and three Supreme Court nominees than it would be with Hilary and her competent execution of an evil ideological agenda. But why the pro-Trump crowd has never seen that they were only delaying the inevitable by defending his behavior is simply beyond me. I think there will be a lot more clarity in a few weeks as to what I have been trying to say here.

I would rather see President Trump than President Biden, as it pertains to the courts and the personnel that fill federal agencies. But I will not defend Trump when he is wrong, and I will not criticize him when he is right. If that makes me persona non grata in the MAGA world, I am okay with it. My operating principle has been to tell the truth, to advocate for truth, and to use whatever influence I can for constructive purposes. The Never Trump world that has abandoned any semblance of reason, rationality, principle, or decorum to devote all effort to hating on Trump has become exponentially worse than what they allegedly sought to correct.

Abandoning conservative ideology because you love Trump is wrong.

Abandoning conservative ideology because you hate Trump is wrong.


I do not believe President Trump is going to win. I believe he won off of an inside straight in 2016 that was never appreciated by his most loyal of supporters. A repeat performance was going to be very difficult in the best of conditions unless he expanded his base. The margins were razor thin, and a failure to expand his coalition or to embrace suburban independent voters has been suicidal. But I believe Joe Biden will make a bad President, and his VP choice would make a reprehensible one. My prayer is that if I am right that Biden will win, that he inherit a Republican majority Senate. Getting passionately behind Collins in Maine and Tillis in North Carolina and Ernst in Iowa over the next few weeks is probably the most effective thing you can do if you care about judges and the like.

But perhaps I am wrong. Perhaps the polls are wrong, and I mean wrong in a way that is not even comparable to what people think was wrong about 2016 (where they really weren’t too wrong). I actually think it will end up being worse than I think, and we may see a blowout far bigger than Romney/Obama in 2012. But again, I have the humility and grace to admit that after 2016, I could just be way, way off. What I will not do is say that because of my problems with President Trump, we ought to get behind Joe Biden. It is convoluted and perverse thinking, and I do not want Joe Biden to win.

But if I am right, and Biden does win, I will not wake up November 4 and say our country is lost. Neither will the vast majority of those who presently claim just that.  If Trump wins, I wake up and have work to do. If Biden wins, I wake up and have different work to do. Either way, I have work to do. And so do you. But if Trump loses, there will be lessons to learn (for all of us), and if he wins the same is certainly true (for one thing, modern polling as an industry will be dead, forever).

Summary: If I lived in a battleground state I would be voting for Trump, without ever defending the policies, personnel, and behavior that do not warrant defense.

I am sorry if this piece is insufficiently critical of the President for some of you, or insufficiently defeatist about a Biden win for some of you.

But it is an honest and humble articulation of my conclusions on this subject. I care for this country deeply, and I fully recognize we find ourselves in crucial times. 2024 is going to be a significant election regardless of who wins in 2020. The time to stand athwart history and yell “stop!” at the forces of progressivism is now. Whatever happens in November, this is no time to get wobbly. The forces required to preserve the American experiment after 2020 will require people who voted for Trump and people who didn’t. I hope everyone reading this article understands that. No matter what you end up doing with your vote and your conscience in a few weeks, please try and appreciate that fact. Our movement will require a gracious on-ramp for people on both sides of this Trumpian divide. Not those who sold their souls – I get that there will be the excommunicated (on both extremes). But outside of both extremes, we will need to find a path to work together for the country and cause we love. That, my friends, is really the best I can offer in these crazy times.