Always Keep Them Guessing

January 2, 2026

Doug Leyendecker

Welcome to This Week’s Leyendecker View

The only way to have a friend is to be one.
– Ralph Waldo Emerson

FAVORITE READS OF THE WEEK

The unseen
Technology and the crisis of loneliness.

What companies are actually doing with AI
Trying to get rid of labor?

FAVORITE VIDEOS OF THE WEEK

What some Russians think of the war
Real voices from Russia.

Did the USS Texas save D-Day?
She partially sank herself to hit the enemy.

THINKING OUT LOUD

Always Keep Them Guessing
Trump’s negotiating process

In sports, there is a strategy of keeping an opponent off balance, constantly pressuring them, forcing them into a reactionary state, rendering them unable to play their game. Football coaches try to do it with play calling. Tennis and other racket sports players try to do it during a match. Sometimes it is referred to as playing “on the front foot” since the strategy is to keep the opponent on their heels. When on their heels, opponents can’t play their game. Instead they are forced into reacting to keep in the game.

Playing on the front foot is an apt metaphor for Trump’s approach to policy and problem-solving, domestic and otherwise. Put another way, it’s his approach to negotiation. And to the mogul whose career has been in real estate and all about closing business deals, Trump—as we should all know well by now—is always negotiating.

If you’ve read Trump’s Art of the Deal, you’ll know his characteristic approach: Go hard. Create confusion. Change course as many times as needed to disarm your adversary. Make them fear you. Get them on their heels. Keep them second guessing. Make it impossible for them to predict your next move. Ultimately, force them to come to the table and acquiesce. Do whatever you must to close a good deal.

We’ve seen this approach play out again and again.

Do we really know where Trump stands on Ukraine and Russia? One day, he’s friendly with Putin. The next, he’s all in with Zelensky. Another day, he is chastising both. He’s going hard when needed, softening up when it’s time, but always trying to cajole both parties to cut a deal.

We see a similar pattern when it comes to tariffs. One day, Trump threatens high tariffs. A week later, he backs off. A month later, there’s another threat. This theater of flip-flopping puts trade partners on the defensive, which is intended to push them to give us better deals.

Then there’s immigration. When, where, and how Trump uses ICE can be unpredictable. This is designed to scare illegal immigrants, perhaps to compel some to self-deport and certainly to send a signal to any considering entering the US illegally. It is also likely to make cities think twice before offering sanctuary to illegal immigrants.

And then when we see President Trump take out Venezuela drug runners and capture oil tankers skirting sanctions, this is to show our adversaries we aren’t afraid to act in our country’s best interests. This should have the effect of making our adversaries, both minor and major, think twice before taking action that goes against productive American and global economic or security interests.

Russia, China, Iran, and North Korea have taken notice. Trump has sent the memo that we’re serious about our own self-interests. We’re not afraid to take action. Even our “friends” in Europe, Canada, and Mexico must now pause before they act, unable to predict how Trump might respond. They know he isn’t fooling around.

All to say, what we hear from Trump or his team is likely less what they want us to know and more likely what they want their adversaries to know or think they know. This is how Trump operates. It might feel unorthodox from the Oval Office, but this is what Trump knows—negotiation as the foundation to value creation and goal achievement. Keep your adversaries on their heels. Keep them confused. Get the deal.

The dance of negotiation, or the art of the deal, is the Trumpian way. His strategy weakens his bureaucratic, economic and geopolitical adversaries, which enhances his MAGA effort. What Trump may be teaching us and the rest of the world is that the world needs the United States more than the United States needs the world.

When you read or watch the news, beware the outrageous headline or outlandish story of the day. Instead, step back and take in the full picture, bearing in mind that it’s often still unfolding. Today’s threat to this person or contingency is tomorrow’s deal. This approach, this metaphorical putting people on their back feet, this constant pivoting, might feel uncomfortable to us in the moment, but the moment is not the point. The deal is.

THE RANDOMS

It appears Putin may not agree to any ceasefire terms. He may not be able to cut a deal that doesn’t result in a complete Russian victory. Doing so would be a failure and make him a target inside Russia.

Is an AI backlash about to pop the AI bubble? Who isn’t bothered by every tech company trying to shove their new AI down our throats? AI we didn’t ask for?

Again and again, we make new scientific discoveries that render previously held “truths” wrong or at least outdated. The latest example: It appears humans are not, in fact, direct descendants of Lucy.

Every time I see a headline asking if China is going to win the AI race, I ask myself exactly what is the goal line we’re all in such a race to reach?

In 1972, video games hit the market with the simple game of Pong. Today, video games represent hundreds of billions of dollars in revenue. Who knew that pickleball was invented in 1965? Today, it’s the fastest growing sport in the country. So what simple thing is new today that in 50 or so years will become a behemoth?

The effects of GLP-1 weight loss drugs look remarkable, but where are their unintended consequences?

Las Vegas is in a big tourist slump. What is this canary in the coal mine telling us?

ECONOMIC NEWS

Economy

Reasons for optimism in 2026
Cooper is the new gold
Will insurance rates fall next year?

Labor

Companies don’t have big 2026 hiring plans

Health Care

Obamacare, a money pit for taxpayers
Pharmacies are scamming patients
Are doctors replaceable?
Is a dementia vaccine coming?

The Lone Star

Dallas is booming, except for downtown
De-carbonization start-up ready to go
Low carbon fuels venture starts in Houston

BUSINESS