Trump's Trade Gambit: Sending Letters When Handshakes Are Impossible

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The clock is ticking on global trade—and boy, is it ever a complicated timepiece.

President Trump, never one to shy away from ambitious deadlines, has essentially admitted what trade experts have been muttering for weeks: you can't personally negotiate 150 separate trade deals in the time it takes most people to decide on kitchen countertops.

"We have, at the same time, 150 countries that want to make a deal, but you're not able to see that many countries," Trump acknowledged during Friday's business roundtable in Abu Dhabi. His solution? Treasury Secretary Scott Bessent and Commerce Secretary Howard Lutnick will start "sending letters out"—essentially dropping tariff notices like parking tickets on diplomatic windshields.

Look, this is classic Trump. Setting impossible deadlines, then adjusting on the fly when reality intervenes. His latest timeline gives nations "two to three weeks" before tariff determinations start rolling out—a subtle extension from his April 23 promise that tariffs would be determined "over the next couple of weeks."

I've covered trade policy since the USMCA negotiations, and one thing holds true: actual trade agreements take years, not weeks, precisely because they're mind-numbingly complex. What Trump's proposing isn't negotiation so much as notification.

So far, only the UK and China have managed to reach framework agreements with the administration. (And let's be honest, the details there remain fuzzy at best.) That leaves about 148 countries scrambling like contestants on some bizarre economic reality show.

India, Japan, and South Korea are supposedly "close" to deals. But what does "close" even mean in this context? It's like saying you're "close" to finishing a jigsaw puzzle when you've only found the corner pieces.

The market implications are... well, complicated.

Even with the 90-day "pause" on the most aggressive reciprocal tariffs, Fitch Ratings calculates the average U.S. tariff rate at 13%—a massive jump from the pre-Trump 2.3%. And the president hasn't been subtle about his endgame, claiming he'd declare "total victory" if import taxes hit 50% a year from now.

For businesses trying to plan inventory or pricing strategies, this creates something akin to navigating blindfolded through an obstacle course. While someone keeps moving the obstacles. During an earthquake.

Markets have responded with predictable whiplash—dropping on tariff announcements, rebounding on negotiation progress. This pattern creates perfect conditions for sophisticated traders who thrive on volatility, while regular businesses and consumers just get the headache.

There's a fundamental contradiction here that deserves more attention. When Trump says, "I guess you could say they could appeal it, but for the most part I think we're going to be very fair," he's describing something closer to a court proceeding than international diplomacy. Countries aren't negotiating partners; they're petitioners seeking relief from predetermined penalties.

(I once watched a similar approach during state-level trade discussions—it didn't end well for anyone involved.)

This might yield short-term concessions and flashy headlines, but it's dramatically reshaping America's role in the global trading system. Whether that's brilliant disruption or economic self-sabotage depends not just on eventual deals but how this uncertainty reshapes global supply chains.

The uncertainty itself has become a policy tool—a kind of economic game theory where countries must decide whether to rush to negotiate now or wait to see what tariff card they're dealt.

In the end, what we're witnessing isn't so much a negotiating marathon as a game of high-stakes musical chairs, with 150 countries circling and precious few seats available before the music stops.

And when it does? Americans will almost certainly be paying more for imported goods. That's the reality no amount of dealmaking—even from someone who wrote "The Art of the Deal"—can fully negotiate away.