What is the difference between a grifter and a strategist?

Answer: one is conniving and the other is cunning.

A grifter thinks that once he has “fooled” someone, he is intellectually superior and can trick, bribe, or bully people he thinks he has now held forever captive. He woos them, and then it is the old bait and switch, banking on complacency.

The strategist makes alliances and is mindful to keep promises and make sure he gives people reason to stay loyal.

People who are conniving are driven by gullibility, ego, and fantasy. People who are cunning are realists who can deal with that reality without hubris.

With 10 days until the US midterms, everything hinges on whether Donald Trump understood this difference, and he did not.

He made deals with the himbo peasantry of Rumble and SubStack to cheerlead for him with big promises of cabinet posts and other patronage positions, but he did not have the votes to secure a win on MAGA alone.

He absolutely needed swing voters, the Independents, to secure his presidency. He understood this in 2016, when he won, not with the popular vote, but with courting the swing states.

He cast a wider net in 2024. Independents worried about the economy. He made a promise that he would focus on that.

So far, so good.

But then the pickpocket billionaires parasitically latched on to Trump and wanted even more because measly billions wasn’t enough for them now. They had to be trillionaires who sucked in all the money and paid no taxes. They were money hoarders, no different than the ones whose houses are overrun with boxes and newspapers from the 1980s.

So, he thought he would merely make it easier for billionaires to suck up all the air and then falsely claim he did something for the economy.

He did for the billionaire economy, but at the expense of the middle-class economy. These two economies have nothing in common.

And this is where everything went off the rails.

Trump is obtuse to nuance. He has no empathy and he is very me-centered. He has primal instincts, but without other literacies, he can only read a room for the short term. His gambit banked on some dicey premises:

1. The Democrats would never focus on the economy.
2. Making billionaires richer would trickle down to the middle and working classes.
3. The Independents would forever be MAGA Republican.

What happened instead was simple:

1. The Democrats focussed on the middle-class economy, courting more voters because there are more working and middle-class voters than there are billionaire voters.
2. Billionaires don’t know when to quit, and will always demand more, more, more because they falsely believe they are entitled and special.
3. The Independents look at the bottom line and switch parties because they are tethered to no political party. They are political atheists. They don’t see themselves as getting married to a party and then get duped into thinking divorce is bad. They will dump you in a heartbeat if you cheat on them.

Trump can’t relate to middle and working class people. He could pander to MAGA because Fox News spent years cultivating this group (not for Trump, for their own ratings and niche), and Trump told them what they wanted to hear. All he had to do was pay attention to them, and as Trump was rich and famous, having a “celebrity” see their worth was enough.

But when people can’t pay their bills and they are worse off than they were two years ago, it’s game over. The spell is broken.

If Trump was smart, he would have hit those billionaires with heavy taxes to humble them, but he has more in common with them than he does with the people who put him into office.

I found this New York Times podcast interesting.

But guest Sarah Longwell had two good observations here:

It’s easy, actually. This is the easiest question in politics right now. Donald Trump made some very specific choices, and they were his choices, and everyone knows they were his choices.

The first one was when he did all of the unilateral tariffs, didn’t consult Congress and just got into trade wars with a whole bunch of people. And the second was starting the war with Iran.

Voters completely identify those two things with Trump. You can’t say Joe Biden did that. You can’t say it was someone else or Congress. There was nothing else.

And this one, which is by far the more astute observation:

But mostly, they thought: This guy is a businessman — and that means that he is going to figure it out. Because this is what Donald Trump pitched all the time: I’m going to cut deals for you. I know how this system works. It’s rigged against you. I’m going to unrig it.

And voters really did think, whether it was because of “The Apprentice” — and I cannot tell you how important “The Apprentice” is and was to the lore that sits inside voters…

…He lived, in their living rooms, at the top of a boardroom where he made decisions about business, and that is what voters really internalized about Donald Trump.

So when inflation was high, they thought he was going to come in, and in some way that is magic from him — sort of like the Kool-Aid Man busting through the window — and say: Here, I’m going to lower grocery prices on Day 1.

They think he has some secret sauce that allows him to do that. When, of course, it is just a lie. He couldn’t do it.

There are three crucial concepts to understand when it comes to manipulation: Curation, narrative, and lore. If you understand anything about video games, lore is a familiar concept, but it applies to world-building fiction in general.

Donald Trump used lore, and yes, he used The Apprentice as a way to cultivate that lore. I always said in the US there are two factors which determine who will be voted into US public office:

1. Which candidate looks more fun at a cocktail party?
2. Which candidate had a starring movie and television career?

The Apprentice did more than just give Trump free advertising: it gave him the chance to craft his own lore: it should be no surprise that the Apprentice had middle-class contestants be tested and vetted by him. He had the eye to see which one was worthy of being his “apprentice.”

He published the book The Art of the Deal, which also contributed to his lore: he could make the best deals. He knew how to negotiate to get what he wants and to win.

He knew how to use the press to create the Myth of Donald J. Trump. In many ways, he was playing the long-game and seemed like a strategist.

But he wasn’t. He had teams he ploughed through over the years and discarded.

And as he alienated more and more quality operatives, he was left with the people with big opinions and tiny SubStacks and Rumbles who wanted a patronage appointment and weren’t going to get it any other way.

And then second group of parasite billionaires ran to him with their list of things they were going to get from Trump.

That meant, by default, he alienated the Independents, banking on their loyalty.

And he is not going to change their minds in 10 days.

Many of them voted in advance. Many have been permanently damaged by his policies. He can’t blame Biden for them. They have his stink all over them.

Going after Canada was the stupidest thing he ever did in his presidency. Canada was a staunch ally and proudly so.

The entire world knew it. He should have left well enough alone. Pierre Poilievre’s Conservatives were on the verge of winning the federal election, but Trump turned out to be an economic terrorist threatening to annex Canada, and lost a potential ally.

He alienated an ally country. He alienated the Independents who gave him a second chance.

That’s all on him, no one else.

He alienated external allies. He alienated internal allies, which is actually a comedic piece of symmetry.

Because that’s exactly how his one-time rival Hillary Clinton snatched defeat from the jaws of victory and lost the 2016 election, despite winning the popular vote.

She blamed Russian “interference” (external) and then FBI Director James Comey (internal) for her failure to win.

It was neither. She ignored swing states to her peril, and instead campaigned in places where she was already secured the electoral votes. If a candidate wins a state, it doesn’t matter if they win by one vote or every voter votes for them, you get only so many electoral votes toward your total. She absolutely had to campaign in swing states to push herself over the threshold. She didn’t; she lost.

Donald Trump didn’t win 2016 so much as Hillary Clinton lost. She didn’t campaign on any you-centered economic platform. Her thesis was that she should be president because it was “her turn.” Being the first female president is not a policy or vision: it’s an egocentric paper crown that may appeal to a partisan base, but it is Independents who decide elections, and they don’t play into those games.

Trump smelled opportunity and strutted into the White House, but then inherited the worst intellectual glitches of Clinton in the bargain.

So Trump’s failure is his own.

The more he uses his old strategies, the worse it becomes for him because that’s why people are now sick of him.

A decade of MAGA brings fatigue. People want something else.

And they will get it.