Because of its desire to preserve traditional social structures, there is a strong tendency toward nostalgia among the right. This tendency is particularly strong in the Boomer generation. Nostalgia, and nostalgia alone, is the reason why Donald Trump looks like a viable 2024 candidate. Anyone who is actually paying attention knows he would lose. History has a mind of its own and it has passed Donald Trump by. Six months out, we must continue to critically examine his legacy. Above all, we cannot allow Trump to become a cult figure like Reagan. Donald Trump is responsible for reinvigorating the Republican Party and presenting a path out of the 80’s fan club it had become, but we can’t allow the same Boomers to create a cult around Trump. As important as he was, he had serious character flaws which prevented him from becoming a truly transformational president and ending America’s Long Humiliation. If we’re interested in actually doing so, we cannot go back. Therefore, we must call out Donald Trump’s 10 Worst Mistakes as President.
Because the attachment to him is so strong, I’ll have to say that this comes not from any position of animus. I supported Trump from almost the moment he came down that escalator, because I recognized his disruptive value. I met him at Trump Tower in November 2015 and got a signed copy of his book. This isn’t personal. Calling out his worst mistakes is strictly business.
10. Deferring to the Federalist Society on Judges
One thing that Donald Trump did do effectively as President was stacking the federal bench, including three Supreme Court Justices. This will be one of the most enduring aspects of his legacy and will certainly be better than their Democratic equivalents had Hillary won.
Yet, one of the worst mistakes came when Donald Trump deferred to the Federalist Society on his judicial appointments. For every Sam Alito in that group, you’ll also get someone who is more obsessed with legal procedure than making the correct decision. You will also get people who tend to defer to government and especially corporate power. Amy Coney Barrett in particular is proving to be someone along these lines.
As a result, the economic and privacy fights we need to make have become harder, since cases may often go in front of a Trump judge that will defer to corporate prerogatives. He simply did not understand enough about this issue to make informed decisions across the board. In 2017 and 2018 there may have been an excuse for this. But by 2019, the writing was on the wall about corporate priorities, and he did not change course. It was one of his worst decisions that will last for years to come.
Because of this, the judiciary is far from what it could have been, and will last as one of Trump’s most enduring mistakes.
9. Donald Trump’s Caring About the Media
Donald Trump tried to present himself as a man who cared not a wit about what the corporate media thought of him. He even branded them (correctly) as the enemy of the American people. Yet, he lost that edginess after he became President. The truth was that he cared an awful lot about them. How else do you explain his over-the-top reactions to any negative story posted about him? Why would Donald Trump invite Bob Woodward into the White House just as the coronavirus was ramping up and give him an opportunity to report badly about him at such a critical juncture – especially when he’d already written a negative book about him during his presidency?
The answer is because Donald Trump was still a Boomer. He might have talked about alternate media all he wanted, but his White House was still traditional in this respect. He came up in a world where the corporate media was the only game in town. Bob Woodward was among the most famous reporters of that generation.
Donald Trump knew they hated him, but wanted them to like him. This was one of his worst mistakes. It resulted in an endless list of unforced errors that distracted from his agenda. Contrast to Ron DeSantis, who works on the understanding that the corporate media hates him, and doesn’t let it distract him. He swats them away like flies with Trumpian panache, but far more logic. Afterward, he doesn’t talk about their stories. He just gets back to work and gets results for his voters, because that’s what matters.
As in professional wrestling, the two sides played off each other to promote themselves. Donald Trump played off the corporate media to get attention, but as President, he already had that. The media got far more out of the kayfabe-style beef than he did once the campaign ended.
Had Donald Trump conducted himself like Ron DeSantis, he probably wouldn’t have lost as many upscale, married white men as he did in 2020, and thus would still be President.
8. Hiring Johnny DeStefano as Director of Presidential Personnel
This little-known decision at the start of 2017, when Donald Trump was still President-Elect, would set the tone for many of the worst mistakes that came after it. Johnny DeStefano doesn’t seem to have a character that is particularly malicious, but he was never truly committed to Trump’s 2016 agenda. He came up in the Republican establishment, among John Boehner and others. As such, his hires reflected the priorities of that establishment, not those of the people that voted for Donald Trump.
If you heard of staffing problems, the conflict between different factions in the White House, and treacherous palace intrigues, Johnny DeStefano was probably the indirect cause of a lot of them.
7. Hiring Christopher Wray as FBI Director
Finally, Donald Trump realized that James Comey had to go. Far too late to stop the Russia hoax from metastasizing, but at least the firing opened the way for the chemotherapy to begin.
And then he squandered that opportunity by hiring Christopher Wray as FBI Director. A career Justice Department bureaucrat, Wray never intended to serve the elected President of the United States, but the unelected ruling class. He not only failed to clean up the FBI during the Russia and Ukraine impeachment hoaxes, but undermined Trump during the Black Lives Matter riots, adhering to the line that “Antifa was an ideology.” In other words, he signaled that there would be no real crackdown on these extremists.
It speaks volumes that of all the Trump-era officials, Wray was the one who stayed under his successor. He has promptly begun a crackdown on Trump’s own supporters in a burgeoning “domestic war on terror.”
In fairness, Donald Trump realized later on that Wray was one of his worst mistakes, but by then he was too entrenched to easily get rid of, and with the Crisis of 2020, the President had other matters to attend to.
6. The Love Affair with the Generals
Like most conservative Boomers, Donald Trump had a love affair with the military. He was of the opinion that hiring former generals into his administration would “make America strong again.” In actuality, the Pentagon had been heavily infested with wokeness during the Obama administration, and many of the generals he hired earned their stars during those years. You do not get to be a flag officer without a certain political acumen, and because cowardice and lack of virtue rule the day, these officers decided it was more politically expedient to go along with the woke craze.
The one thing these generals cared more about than wokeness, though, was the good of the national security state. That meant maintaining the “endless wars” that Trump ran on ending.
As such, when Donald Trump brought in people like James Mattis, John Kelly, HR McMaster, and so on, he empowered the Military Industrial Complex that he had run against. The result was a failure to end the wars he had pledged to end. James Mattis famously resigned and became an avowed enemy of Trump in December 2018, after the latter insisted on withdrawing all troops from Syria. John Kelly, likewise, became an avowed enemy and distraction after leaving the White House.
He did arrange for the withdrawal of American troops from Afghanistan, but too late to get the credit for it. It will now go to his successor. He made this bureaucratic task more difficult because of the national security state alumni that he hired. It was truly one of his worst mistakes.
His empowering of “the generals” also did nothing to stop the woke takeover of the military. Quite the contrary, it accelerated. Joint Chiefs Chairman General John Milley made headlines recently when he started talking about “white rage.” Milley was one of Trump’s hires and undermined him during the BLM riots last summer. The President imposed no consequences for this insubordination. Others like him who felt the same also saw promotions in Trump’s time.
The swamp in the Pentagon was not drained. Instead, it got deeper. Now we have an out and out woke military which is more concerned with pronouns, race baiting, and policing “extreme” Americans than winning wars. As the world grows more dangerous, we can partially blame Donald Trump if we suffer Troy’s fate. Promoting “the generals” was one of his worst mistakes, but at least it revealed how deep the corruption goes.
5. Failing to Purge Obama-era Bureaucrats
As soon as the mummy entered office, his handlers purged Trump-era appointments in the Justice Department and the national security-related bureaucracies. They promptly replaced them with their own people. Trump’s presidency started with no such thing. Many Obama-era officials lingered on deep into Trump’s tenure. They promptly colluded with their colleagues in the corporate media to leak damaging rumors and innuendo. This was how the Russia hoax got so much traction. Donald Trump did eventually fire James Comey, one of the ringleaders in setting that hoax up, but far too late, and many others remained.
We saw this in the first impeachment sham. The alleged “whistleblower” who began the tragicomedy, Eric Ciaramella, was an Obama national security holdover. Almost everyone else involved in that particular coup were either holdovers or people that never should have been in the Trump administration to begin with.
One gets the impression that Donald Trump didn’t even realize the mistakes he was making and that staffing was simply not a high priority for him. Whatever the case, this was one of his worst mistakes of all.
4. Deferring to Paul Ryan on Legislation
When he entered office, Donald Trump had a historic opportunity. For the first time since 2006, there was a united Republican government. It had a healthy House majority and a narrow Senate one. Donald Trump ran on a robust agenda in 2016, one which proved more popular than any “expert” had imagined (though I knew its strength). Time was of the essence. Immigration and industrial policy, the two biggest domestic items of his successful campaign, needed attending to.
Rather than articulating his big ticket items in 2016 into a realistic legislative vision, however, Donald Trump instead deferred mostly to Paul Ryan. It was one of his worst mistakes of all. Paul Ryan was the foremost representative of the very establishment Donald Trump repudiated in 2016. As such, 2017 and 2018 were spent on traditional Republican items rather than the agenda Trump won the presidency on.
Instead of a move to replace the 1965 immigration act with a merit-based system, we got a haphazard mess of an attempt to repeal Obamacare. The Democrats successfully pinned this ill-coordinated mess into a message that Republicans were taking away Americans’ healthcare. This drove up turnout and added to the Republican defeats in 2018.
Instead of pinning any business tax cuts to reindustrialization and made-in-America provisions, we got a generic tax cut for the companies that hated Republicans and their voters anyway. It was among Trump’s worst decisions and came back to haunt him.
And, in a deviation from his “law and order” agenda in 2016, President Trump pushed the First Step Act through Congress, thanks in part to gladhanding with celebrities like Kim Kardashian. This act released criminals early, during the midst of an uptick in crime. It’s too early to tell for sure, but it might well have contributed to the skyrocketing levels of crime seen in 2020 and 2021. It is certain that Trump’s approval rating fell in the rust belt after the First Step Act.
These legislative mistakes ensured that he would not be a transformational President.
3. Not Going After Big Tech
A few weeks ago, Donald Trump put out a press release essentially admitting that he did not go after big tech because people like Mark Zuckerberg said good things about him. One could not ask for a more open admission of failure. By the back half of 2018, big tech’s intentions were clear.
When he saw that his own supporters getting censored and deplatformed, President Trump infamously tweeted that he was “monitoring the situation.” That set the tone. Big tech understood that there would be no retaliation from the White House. The President failed to push the Republican Congress into taking action on big tech, either, ceding antitrust initiatives to the Democrats. Worse for him, big tech put its thumb on the scale in the election, censoring news about Hunter Biden’s business dealings in the critical weeks before voters went to the polls.
Trump’s recent lawsuit against big tech is comical, in the sense that he did not take any action when he actually had power. It was one of his and the Republican Party’s worst mistakes.
2. Hiring Jared Kushner
Many of the poor staffing decisions, the worst legislative mistakes, and general sense that the President was not fully living up to his 2016 promises (despite the “Promises Made, Promises Kept” slogan), can be traced to one person. This person was the de facto Prime Minister of the United States from 2017-2021, with an absurdly large portfolio. It was Trump’s son-in-law, Jared Kushner. Bringing him on was hands-down one of Trump’s worst mistakes.
In everything from letting criminals out of jail, to failure to crush the riots, to broken promises on immigration reform (in particular the “temporary” work visas), Jared Kushner was involved. He convinced the President that African-Americans were crucial to his reelection and to take the white working class for granted. As such, the administration had many misplaced priorities. It resulted in campaigning on criminal justice reform as criminals ran riot from coast to coast. It resulted in talking about a “platinum plan” while the very working class which constituted Trump’s base suffered from coronavirus lockdowns.
The endgame? The President lost just enough white working class support to tip the election. He improved his black margin by a point or so. It was clearly a bad trade. Can anyone think of something which could rank higher among Trump’s worst mistakes?
Unfortunately, I can.
1. Elevating Anthony Fauci
This was without question the worst mistake of all. Of all the other mistakes on this list, none of them would have proven fatal for Trump’s re-election on their own. For all his flaws, the President had a remarkable durability. They didn’t call him “Teflon Don” for nothing. This “antifragile” aspect to him was a major theme in Stumped.
The secret to Trump’s success was his ability to remain at the center of attention. Everything came in reaction to him, so his opponents were not proactive. No one could define themselves separately from him. Even the Russia and impeachment hoaxes failed to change this. I detailed this “spatial domination” dynamic in Stumped’s second chapter.
As the “Godfather of Influence” himself says – attention is importance. It is a quality all on its own.
Then Trump’s fortune got hit with a freak virus from China. To respond to it, he elevated a little-known bureaucrat, Anthony Fauci, to the point of superstardom.
Chapter four in Stumped details how politics is basically a professional wrestling show. There are babyfaces, heels, and stories between them that promoters need to calibrate to audience tastes. For ages, Trump’s opponents had no real babyface that they could promote to credibly challenge him and cast him as the ultimate heel. All of their presidential candidates were duds and the economy was booming.
Then came the virus, which exposed Trump’s inherent character flaws, and Fauci, who reflected off of them. As the President overexposed himself with incoherent, rambling press conferences when people felt afraid, Fauci, by contrast, felt like the mature “expert” in the room. Finally, the corporate media found their guy. They cast Anthony Fauci as the heroic babyface against Trump’s being the worst of all heels. Fauci soon became the corona czar and rendered anything the President had to say irrelevant.
Unfortunately, the President did not do the proper due diligence. We quickly discovered that Fauci was a self-interested bureaucrat who was often wrong and craved fame more than anything else. By the end of April, data became available which suggested that Fauci’s prediction about the coronavirus’ danger was incorrect and that only elderly people truly needed protection. The masks, the “distancing,” the lockdowns – all were unnecessary. Ron DeSantis reopened Florida when he got hold of this data.
President Trump did nothing. He did not calmly explain this data and made no move against Fauci, despite his growing failures and malevolence. This oversight proved fatal. By May, Fauci had firmly entrenched himself, along with the belief that the President had “failed” on the virus. Trump’s was no longer the dominant voice in the country. Anthony Fauci had become a de facto dictator whose word was law in wide swathes of the country. Joe Biden simply grew in the cracks of Trump’s rapidly crumbling authority.
By summer, when Scott Atlas came onboard, the President realized he had made this worst of all mistakes, but far too late. He had by that point become a king without a throne. The Black Lives Matter Riots, the prolonged misery, growing tech censorship – all came because of the lockdowns Fauci advocated and gave air cover to.
This worst of all mistakes single-handedly cost Trump the Presidency. It serves as a stark warning that Louis XIV elaborated on in his memoirs:
Men are always tempted to use the power they have. No one shares in your work without participating in your power. Leave only as much of it to others as you must, for however careful you are, you will always lose much more of it than you should.
Most of the worst mistakes of Trump’s time as President come down to these words. They must not be repeated. His character has not changed. Any talk of 2024 is delusional.
For more on Louis XIV and the proper conduct for those in power, read Lives of the Luminaries. It will help you avoid making Trump’s worst mistakes.
Hire me if you liked this post.