Spear Phishing, Drone War and The Election

“War is the continuation of politics by other means.”

–Carl von Clausewitz

We were preparing to release our latest interview with Grey Swan contributor John Robb, when a few news items crossed the transom.

Over the weekend, the Trump campaign announced that “foreign sources hostile to the United States” had accessed some private communications and documents from its network using AI modules.

A Microsoft report corroborated, announcing hacker groups connected with the Iranian government “sent a ‘spear phishing’ email in June to a high-ranking official on a presidential campaign.” The report continues:

They’ve laid the groundwork for influence campaigns on trending election-related topics and begun to activate these campaigns in an apparent effort to stir up controversy or sway voters—especially in swing states. [And] launched operations that Microsoft assesses are designed to gain intelligence on political campaigns and help enable them to influence the elections in the future.

Microsoft added that an Iranian group has been launching covert news sites targeting US voter groups on opposing ends of the political spectrum:

One of the sites, called Nio Thinker, caters to left-leaning audiences and insults former president Donald Trump, calling him an “opioid-pilled elephant in the MAGA china shop” and a “raving mad litigiosaur.”

Another, called Savannah Time, claims to be a “trusted source for conservative news in the vibrant city of Savannah” and focuses on topics including LGBTQ+ issues and gender reassignment. The evidence we found suggests the sites are using AI-enabled services to plagiarize at least some of their content from US publications.

The cynic presumes the worst.

In our “wag the dog” scenario, we immediately suspected the “news” had been pounced on by the Trump campaign because the “honeymoon” period of Kamala Harris and Tim Walz trying to rally the Democratic base was stealing headlines from their own post-assassination-attempt, Republican National Convention, and JD Vance announcement buzz.

Either way, another news report from the Associated Press indicates, “U.S. Defense Secretary Lloyd Austin has ordered a guided missile submarine to the Middle East and is telling the USS Abraham Lincoln aircraft carrier strike group to sail more quickly to the area, the Defense Department said Sunday.”

As we track government spending, the national debt cresting $35 trillion, and the real motives for conflict in Ukraine, Israel and all across the Middle East, the motives for various details get murky.

“We’re in a networked world,” we’ve only recently noted to Mr. Robb. “Can the U.S. even win a forever war? Or is it just perpetually expensive.”

His response was not very encouraging. John Robb:

The US has been trying to manage the global situation for quite a while and has been doing a relatively bad job of it.

Top-line governments and nation-building stuff tend to backfire and haven’t yielded the results that we wanted. But now we see something relatively more dangerous. We’re already on an almost inevitable course towards conflict with China and Russia and most of Asia.

During the buildup, China has been producing a lot of drones.

They have the capacity to produce millions per month. And right out of the starting gates and they could use those drones to supply groups like the Houthis that are hard to attack because they are relatively remote.

Yet, the Houthis can use those drones or any group like that could use those drones to erect aerial denial blockades of sea air and land upwards of 500 to a thousand miles distant from their location.

Seems like a minor detail, but moving a submarine into the Mediterranean capable of launching long-range cruise missiles is an escalation – during a critical election already besieged with AI-induced “misinformation”… well, it’s caught our attention.

We’ll reveal more of our wide-ranging discussion with John tomorrow. His insights into “netwar” are alarming, at best.

So it goes,

Addison Wiggin,

Grey Swan

P.S. While watching JD Vance speak on C.B.S.’ Face the Nation this weekend, we came up with this suggestion for the Republican strategists: One up Harris and Walz by having Trump drop out of the race and grab all the headlines during the Democratic National Convention.

Trump has already remade the RNC in his image. They’d just need to throw in a new VP candidate and a couple aggressive debates. Vance is far more articulate about policy than either Trump or Harris.

Heh. Thoughts? Send them here: addison@greyswanfraternity.com

“War is the continuation of politics by other means.”

–Carl von Clausewitz

We were preparing to release our latest interview with Grey Swan contributor John Robb, when a few news items crossed the transom.

Over the weekend, the Trump campaign announced that “foreign sources hostile to the United States” had accessed some private communications and documents from its network using AI modules.

They’ve laid the groundwork for influence campaigns on trending election-related topics and begun to activate these campaigns in an apparent effort to stir up controversy or sway voters—especially in swing states. [And] launched operations that Microsoft assesses are designed to gain intelligence on political campaigns and help enable them to influence the elections in the future.

Microsoft added that an Iranian group has been launching covert news sites targeting US voter groups on opposing ends of the political spectrum:

The cynic presumes the worst.

“We’re in a networked world,” we’ve only recently noted to Mr. Robb. “Can the U.S. even win a forever war? Or is it just perpetually expensive.”

His response was not very encouraging. John Robb:

The US has been trying to manage the global situation for quite a while and has been doing a relatively bad job of it.

Top-line governments and nation-building stuff tend to backfire and haven’t yielded the results that we wanted. But now we see something relatively more dangerous. We’re already on an almost inevitable course towards conflict with China and Russia and most of Asia.

During the buildup, China has been producing a lot of drones.

They have the capacity to produce millions per month. And right out of the starting gates and they could use those drones to supply groups like the Houthis that are hard to attack because they are relatively remote.

Yet, the Houthis can use those drones or any group like that could use those drones to erect aerial denial blockades of sea air and land upwards of 500 to a thousand miles distant from their location.

We’ll reveal more of our wide-ranging discussion with John tomorrow. His insights into “netwar” are alarming, at best.

So it goes,

Addison Wiggin,

Grey Swan

Heh. Thoughts? Send them here: addison@greyswanfraternity.com

Our forecast will feel obvious in hindsight and controversial in advance — the hallmark of a Grey Swan.

Most analysts we speak to are thinking in terms of the history of Western conflict.

They expect full-frontal military engagement.

Beijing, from our modest perch, prefers resolution because resolution compounds its power. Why sacrifice the workshop of the world, when cajoling and bribery will do?

Taiwan will not fall.

It will merge.

Wars, technology races, and political upheavals — all of them rest on fiscal capacity.

In 2026, that capacity will tighten across the developed world simultaneously. Democracies will discover that generosity financed by debt carries conditions, whether voters approve of them or not.

Bond markets will not shout so much as clear their throats. Repeatedly.

Taken together, the seven Grey Swans of 2025 behaved less like isolated events and more like interlocking stories readers already recognize.

The year moved in phases. A sharp April selloff cleared leverage quickly. Policy shifted toward tax relief, lighter regulation, and renewed tolerance for liquidity. Innovations began to slowly dominate the marketplace conversation – from Dollar 2.0 digital assets to AI-powered applications in all manner of commercial enterprises, ranging from airline and hotel bookings to driverless taxis and robots.

Back in April, when we published what we called the Trump Great Reset Strategy, we described the grand realignment we believed President Trump and his acolytes were embarking on in three phases.

At the time, it read like a conceptual map. As the months passed, it began to feel like a set of operating instructions written in advance of turbulence.

As you can expect, any grandiose plan would get all kinds of blowback… but this year exhibited all manner of Trump Derangement Syndrome on top of the difficulty of steering a sclerotic empire clear of the rocky shores.

The “phases” were never about optimism or pessimism. They were about sequencing — how stress surfaces, how systems adapt, and what must hold before confidence can regenerate. And in the end, what do we do with our money?!