Dear Caolan Robertson, Asymmetric Warfare Does Not Reward Hope—It Punishes Wishful Thinking
- john raymond
- Jul 13
- 3 min read
Caolan Robertson’s recent interview, rich in sincerity and full of moral urgency, nonetheless reveals a profound misunderstanding of the war we are in. He hopes—perhaps even believes—that Donald Trump might finally pivot toward a hardline posture on Ukraine.
Caolan imagines that tough talk might signal a meaningful strategic shift. And he floats the fantasy that a 500% oil tariff on nations still purchasing from Russia could collapse Putin’s war economy. But all of this is mistaken. In asymmetric warfare, hope is not a strategy. In fact, it is often the bait.
The basic error here is one of assumption: that Trump means what he says. That his rhetoric aligns with his goals.
But the long, unbroken pattern of Trump’s behavior shows precisely the opposite. Trump has long said one thing and done another. He has praised Putin, undermined NATO, delayed aid to Ukraine, and shielded Russia from consequences.
And every time he appears to grow tough—every time he “talks big”—he follows it with a maneuver that serves Moscow’s interests.
The mistake is not in hoping Trump might change. The mistake is in failing to see that the appearance of change is itself a tactic.
Words don’t shape reality. Actions do. And until Trump’s actions align with democratic objectives—until aid flows without sabotage, sanctions are imposed rather than floated and withdrawn, and allies are unified rather than fractured—there is zero reason to be hopeful.
In fact, apparent toughness from Trump should trigger even greater skepticism. Because if you’ve studied his playbook, you already know: the “tough talk” is usually a prelude to the next gambit.
Consider the recent 500% tariff proposal—marketed as a threat to punish China or India for buying Russian oil. On its surface, it sounds aggressive. But its real function is almost certainly inverted.
These tariffs are clearly not designed to punish loyalists of Putin. They’re meant to discipline wavering ones—those drifting from Moscow’s influence.
The mechanism is simple: Trump threatens massive economic penalties. Putin then contacts the targeted state and offers a bargain—reaffirm your allegiance, and I’ll make sure Trump backs down.
This isn’t theory. It just happened...
On May 9th, Xi Jinping made a performative show of allegiance to Putin—an embrace broadcast with great symbolic fanfare. Within hours, Trump’s tariff threats toward China were rescinded.
The timing wasn’t coincidental. It was choreographed. Trump tariffs were a loyalty test—and Xi passed. What appeared to the West as a threat was in fact a signal.
The same pattern is now playing out again. The new round of 500% tariff talk is not a punishment waiting to be activated. It’s a lure, designed to pull Modi and others back into Putin’s orbit. If they comply, the threat will disappear. The whole premise, once again, a fiction.
Robertson’s willingness to applaud Trump if he delivers a “just peace” for Ukraine is emotionally understandable—but strategically dangerous. Because the people most empowered by that applause are the ones designing these illusions.
In asymmetric warfare, ambiguity is a weapon. Misdirection is policy. And the more the West clings to fantasies of Trump the Redeemer, the more power Trump has to sabotage Western and Ukrainian goals while pretending to support them.
None of this is to dismiss Robertson’s values. He clearly wants to see the war end, Ukraine survive, and Putin defeated. But noble goals don’t absolve poor strategy. Good intentions are not enough in a war built on deception.
To understand this conflict, one must study the patterns—not the postures.
And the pattern is this: when Trump talks tough, someone is about to be played. When he waves the stick, it’s to reward a favor behind closed doors. And when he promises decisive leadership, what often follows is capitulation disguised as strength.
The truth is, Trump does not use tariffs, speeches, or sanctions to hurt autocrats. He uses them to enforce loyalty to the Kremlin. He punishes hesitation, not aggression. He rewards performative allegiance, not principle. And he relies on well-meaning analysts to misread his signals, spread false optimism, and dampen the alarm bells.
It is this blindness—not some foreign weapon—that threatens the cohesion of the West more than any missile or drone.
In this kind of war, hope must be earned through results, not gestures. It must be built on action, not assumption.
Robertson believes that Trump’s recent behavior might mark a turning point. But history—and recent history in particular—demands the opposite conclusion.
Until Trump proves otherwise through concrete, verifiable policy aligned with allied interests, we must assume his moves serve Moscow. Not Kyiv. Not Brussels. And certainly not democracy.
So yes, this is asymmetric warfare. And in asymmetric warfare, the cardinal sin is trusting the illusion.
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