If Donald Trump does run for re(ish)-election in 2024, some of the obstacles will be the same as in 2020, some will be different, some will depend upon the ever-shifting vagaries of the political landscape, and some will depend wholly upon Trump doing what he does best while avoiding what he does worst.

To start with, there will be the legal issues.  Despite the utter absurdity of the challenge, Marc "I can't believe I'm not at least wearing an ankle bracelet" Elias and his horde of Democrat lawyers will challenge Trump's ability to serve based upon his participation in an "insurrection."  (One of the reasons that term will be used, literally and figuratively, ad nauseam in the January 6 committee report will be to lend a wafer-thin layer of credence to the claim).  Those challenges will take place at every level of the judicial system: local, state, and federal (the warm-ups are already happening), at the very least to inflict political damage, if not actually create a legal bar to his running and, unlike the lackadaisical response to the wholesale voting law changes enacted in 2020, must be met head-on.

This legal effort will work hand-in-glove with Deep State usual suspects leaking like a racehorse made out of a sieve everything they can think of to upend his candidacy.  While nearly all of the leaks so far have been false and the credibility of the national security apparatus is burned toast dropped butter-side down, that will not stop the actual mis-dis-information from being joyously disseminated.  ("Trump's Men from Mar-a-Lago; FBI Finds Evidence of Cloning Facility Meant to Create Swing State Voters," will blare a Washington Post headline...well, maybe not exactly, but you get the point.)

What will work against this is the simple fact that times are changing and will change ever more in the next two years.  Even Democrat strategists understand that the lies have been so transparent that they will only pick at the margins of Trump's support (though the odds are pretty good that there were at least an election-changing 40,000 white guys who couldn't bring themselves to vote for Trump in 2020 because they were told doing so meant they were racists) and are only truly effective as part of driving the base to the polls to vote Democrat in a fog of feckless fear.

It is also true that Big Tech will put their thumb — who am I kidding? — they will put thousands of bodies, millions of dollars, and billions of clicks on the electoral scale.  But the public wariness — and awareness — of such activities is growing, so the push may not play such a decisive role in 2024.  In other words, the Hunter laptop trick — which, even with the completely unsecure voting rules in place, indisputably changed the result of the election — will be harder to pull off.

Strategically, Trump can still run as an outsider even though he has already held the most insider job on the planet.  But if there is a primary challenge, he will lose one of his most effective 2016 tactics.  Unlike every past nomination battle in which the candidate says, "I'm better than the rest because...," Trump picked off his opponents one by one.  Jeb, then Marco, then Ted, etc. all felt the individual wrath of the Trump strategy, leaving him as the last man standing.  This concept — brilliant and based on Trump's no-holds-barred personality — will be tougher in a smaller field.

As to the personality issue, Trump was elected in 2016 because he was Trump.  As noted above, no other candidate used the same strategy, grasped the true feel of the moment and the mood, or could better represent the growing concern of Americans worried that things were going very wrong. 

He came up short (maybe) in 2020, in part, because of the same driving personality issues and even then just barely, an astonishing feat for a person who was demonized by every major media outlet non-stop for five straight years.  Exit polling showed that if any other human had done exactly what Trump actually did as president, he would have been easily re-elected, even with COVID and the disgusting and actually democracy-threatening change to the voting rules.

That personality — when he listened to it — served him well in office at times.  Operation Warp Speed epitomized Trump's "damn the torpedoes" attitude and was a clear success.  Only when he listened to official government doctors — Fauci, Birx, etc. — did he get it wrong.  What was clear was that he felt out of his depth as the doctors drowned him with (questionable) facts and figures; like most of us, prior to COVID, he most likely actually trusted "scientists" to try to get it right, to have the proper experience, and to keep extraneous factors like politics out of the decision-making process.  Not tossing them aside in favor of a Great Barrington Declaration–type approach in the summer of 2020 was an unforced error; at a time when he should have gone with his gut, he went with his head.

Another personality-related error was making the assumption that once he took office, people would — like when he would buy a company or land or whatever — actually have to do what he said.  This assumption kneecapped his presidency from the start, an assumption he will clearly not make if elected in 2024.

This issue also impacted his presidency in another way — being rather unprepared for office.  The Clinton campaign spent tens of millions of dollars — money that they should have spent on TV ads in Wisconsin, it turned out — building her administration months before the actual vote, which she — and so many others — thought was going to be a mere formality.  Hillary did this in part because of the conventional wisdom assumption, in part because she's a bit of a control freak, and in part because she — under no circumstances — wanted any Obama people left around her administration.

She did not forget that he actually beat her, taking away her rightful eight years as president, and she wanted to be absolutely sure there was no lingering odor of — or internal opposition from — Obama's worshipful minions.

Trump did not do this, either because he really didn't understand the depth of the power of the appointed and/or permanent bureaucracy, and was faced with an actively hostile and utterly disloyal raft of people he was in theory supposed to depend upon.  It is quite possible Trump's campaign staff didn't prepare better because they were focused elsewhere, or even maybe thought he wouldn't win, but the legacy of that problem lives on even today.

In his campaign, he promised to destroy the Deep State, and they noticed.  The mortgages, private schools for the kids, good brunch invitations, societal acceptance, and the personal power of its denizens were directly and actually — not existentially — threatened by Trump, and they reacted as one would expect.  Going into 2024, Trump must have a concrete, workable plan to actually do the job he promised to do in 2016.  When one aims to kill a king, one cannot miss.

Trump also ran into the problem of the truth of the oft-quoted line that his supporters take him seriously but not literally, while his opponents take him literally, but not seriously.  In his second campaign — and term — he must understand that and tailor his messaging accordingly (though, no matter what, the media will continue its psychotic drumbeat, and the NeverTrumps will never quit.)

In other words, if he gets good lawyers, good advice, good intelligence on the entrenched opposition, and good people to help him prepare to re-take office, he just might have more than a very, very good chance of taking up residence at 1600 Pennsylvania Avenue again.

Oh, and one suggestion — on January 21, 2025, don't forget to declassify everything.

Thomas Buckley is the former mayor of Lake Elsinore, Cal. and a former newspaper reporter.  He is currently the operator of a small communications and planning consultancy and can be reached directly at planbuckley@gmail.com.  You can read more of his work at  https://thomas699.substack.com.

Image: Gage Skidmore via Flickr, CC BY-SA 2.0.