By Jeremy Kinsman

September 16, 2026

Historians will look back at today’s political and geopolitical chaos and point the finger at two authoritarian leaders who took wrecking balls to international cooperation: Vladimir Putin and Donald J. Trump.

They will cite their shocking respective failures in starting and losing unilateral wars of choice, Russia in Ukraine, and the United States against Iran.

Though there is no end in sight to either conflict, both leaders have fallen far short of their own professed objectives — in both cases poor substitutes for just casus belli — at great cost to their countries.

Both Putin against Ukraine and Trump against Iran have failed because they fatefully underestimated their adversaries’ resilience.

Even after debacles in Vietnam, Afghanistan and Iraq, Trump apparently still believed that a war could be won with superior military force alone. He and his administration continued to under-credit the motivating power of patriotic homeland defence, and failed to foresee asymmetrical warfare that evened the odds.

The U.S. and Russia put forward their own homeland defence as insistent rationales for attacking Iran and Ukraine respectively, citing hypothetical nuclear threat from Iran, and imaginary “encirclement” of Russia by NATO. Neither threat hypothesis has been sufficiently convincing to justify the calamitous costs of their ill-planned wars, including to national stature.

The U.S. military concluded wrongly from the remarkable success of the U.S.-led coalition to evict Iraq from Kuwait in 1991 (the one big war the U.S. had won since World War II): that it was due primarily to technology-driven military superiority and its “shock and awe” effect on an enemy that wilted under U.S. air-war dominance.

They forgot the role played by the “Powell Doctrine” — General Colin Powell’s formula of a million-strong 34-nation coalition force to support a ground attack by 250,000 US troops to overwhelm Iraq in the first Gulf War, as well as the diplomatic effort to obtain the legitimacy of a mandate from the UN Security Council.

As with so many American blunders rationalized by Donald Trump’s inexperience and volatility, the U.S. undertook the massive attack on Iran with no immediate rationale, no coherent plan, no exit strategy, and a coalition of two — itself and Israel.

Russia, too, assumed in-built advantages of scale over Ukraine, notably a 5-to-1 advantage in population, and the vastly greater Russian territory that thwarted both Napoleon and Hitler, feeding the mythology that Russia was immune from attack.

Putin vaunted that military history to convince Russians of his plan for a swift invasion, occupation, and overturning of Ukraine’s elected government. He forgot that when Russian and Soviet forces undertook expeditionary wars beyond Russia’s borders — in World War 1, or against Japan, Finland, or in Afghanistan — they failed.

Neither the U.S. nor Russia anticipated the decisive emergence of cheap, precision-targeted, drone technology that both Iran and especially Ukraine developed and then deployed against them, in asymmetrical warfare that is likely everywhere to change military strategic doctrine.

The U.S. and Israel reportedly underestimated the Iranian supply of drones, missiles, and intact launching sites.

The Iranians have not only deployed their own, cheap Shahed drones both tactically (swarming and saturation, cost asymmetry, launch mobility) and strategically (economic coercion, horizontal and vertical escalation, global industrial networks) they’ve excelled at shooting down U.S. drones.

As with so many American blunders rationalized by Donald Trump’s inexperience and volatility, the U.S. undertook the massive attack on Iran with no immediate rationale, no coherent plan, no exit strategy, and a coalition of two — itself and Israel.

The role Iranian drones have played in threatening maritime traffic that challenges Tehran’s stranglehold over the Strait of Hormuz has wreaked havoc with oil and gas prices, creating what some have called a “second war’ on the global economy.

Meanwhile, Ukraine’s use of drones to outwit Putin was the major military story of much of this year, ironically upstaging the unprecedented spending spree of NATO members on sophisticated and costly hardware from submarines to jet fighters by decimating Russia’s energy infrastructure and compelling a shrinkage of Putin’s May Day parade so it would be a smaller target. All accomplished with the David-vs.-Goliath slingshot of $2,000 drones.

As Canada’s former ambassador to the United States, Derek Burney, wrote in his May Policy piece Drones Don’t Wear Boots: The Battlefield Education of Vladimir Putin: “Drones don’t eat, they don’t march, they don’t die of exhaustion, and they don’t wear boots.”

Putin has roared back, trying to crush Ukrainian morale by attacking civilian targets now that the U.S. has ceased to provide anti-missile defences to Ukraine (having depleted its own stocks against Iran), with winter coming. He will undoubtedly continue to underestimate Ukrainian resilience.

Trump’s admonition this week that Ukraine must no longer attack Russian energy infrastructure is a shocking confirmation of Ukrainian President Volodymyr Zelensky’s greatest fear. He told CNN’s Fareed Zakaria that there have been two calamities for Ukraine: Russia’s criminal invasion and Trump’s end to material and military support for Ukraine.

At their meeting in Alberta this week, Prime Minister Mark Carney and Zelenksy unveiled a “100-year partnership” that includes a deal to manufacture Ukrainian drones on Canadian soil, where the factories can’t be struck by Russia. The agreement underscores Canada’s appeal as a secure haven for not just Ukrainian military technology, but as a global digital sovereignty sanctuary.

Trump appears to be no more competent at peace than he is at war, with the Rosencrantz and Guildenstern of shuttle diplomacy — Jared Kushner and Steve Witkoff — utterly enthralled by Putin, out of their depth on Iran, and therefore only adding to the U.S. credibility crash that Trump’s shambolic foreign policy has wrought.

Though there is talk of a tripartite Summit between Ukraine and Russia with the US as “mediator,” no end appears in sight for the war, nor for a comprehensive resolution of the stalemate over the Strait of Hormuz.

In the meantime, other countries are drawing their own conclusions. The group of NATO countries committed to helping guarantee Ukraine’s security if an acceptable truce becomes possible are working hard to organize an expeditionary multi-country protective coalition that includes Canada.

It is ironic that by now, the strongest military in Europe is actually Ukraine’s. NATO will depend on Ukraine for Europe’s defence as much as vice-versa. The geopolitical likelihood is that a frozen war will eventually apply to Russia/NATO/Ukraine for years to come, or until Putin has left the scene.

The upshot is that in the Middle East, the U.S. has lost control and influence, though Trump apparently finds it difficult to pull out altogether if he seems a clear loser. Ally Saudi Arabia is deepening a hedging military alliance with Turkey and Pakistan. Gulf States struggle to work out a Hormuz navigation formula with Iran.

And meanwhile, China smiles.

In the region and beyond, democracies and other states anticipate the outcome of Israeli elections October 27 to judge whether Israel will retain a government of constant war.

Two hyper-nationalist autocrats, Trump and Putin, have pushed the world toward the brink of chaos, while paralyzing the international system’s capacity for useful cooperation.

As U.S. unreliability under Trump becomes accepted as a reality, Europe, Canada and others are changing gears to help new multilateral coalitions meet agonizing global humanitarian, climate, and developmental challenges, and safe adaptation to transformative technological change.

And meanwhile, history watches with apprehension this shift from the post-Cold War era into a new unknown.

Policy Columnist Jeremy Kinsman served as Canada’s ambassador to Russia, high commissioner to the UK, ambassador to Italy and ambassador to the European Union. He is a Distinguished Fellow of the Canadian International Council.