By Maria Popova

October 22, 2026

When Donald Trump waived congressionally approved sanctions on Russia, announced a deal to buy Russian diesel, and returned to his invective against Ukrainian President Volodymyr Zelensky, commentators rushed to declare a pivot and called it an “October Surprise”.

Washington, they said, had turned against Kyiv. Zelensky called out the betrayal in interviews with American and European media and suddenly Ukraine’s access to Starlink and U.S. intelligence stopped.

Finally, recognition is trickling in that Trump — after years of being ridiculed in the international community and mocked by late-night comedians for his autocratic affinity with Vladimir Putin — has shifted the United States under his presidency from disturbingly amenable to Putin into a full-blown strategic ally of Putin’s rogue state.

The outrage is warranted, but the surprise is not.

This is not a pivot. It is the latest step in a policy Trump has pursued, consistently and in the same direction, since his first term. As with so many of his worst diplomatic and strategic offences against the rules-based order, against democracy, and against America itself, he has merely doubled down since his second term began.

That double-down includes the gaslighting component of what can now be called Trump and Putin’s war on Ukraine, hence Trump envoy Steve Witkoff’s flattery of Putin as a “humanitarian” on Wednesday for releasing an American who should never have been taken hostage.

By turning the U.S. from Ukraine’s most powerful ally under Joe Biden to Russia’s most powerful ally with his latest interventions in the conflict, Trump is clearly serving to shift the underdog narrative of Ukraine’s refusal to be conquered via unlawful aggression into a stunning reversal for the illegal aggressor.

In January 2025, the United States was a cautious but reliable ally of Ukraine. The Biden administration’s escalation management approach at times limited Ukraine’s defence, but the policy was transparent, and military aid was significant. America stood unmistakably with Europe and NATO in defending Ukraine and the principle of territorial integrity.

The first stage of Trump’s policy was to abandon that position.

The U.S. became a “both-sides” observer, treating an aggressor and its victim as equals in a dispute to be settled by a compromise that rewards the invader in the name of peace. New military aid stopped, and Washington began pressuring Ukraine to accept Russian demands that would never have been on the diplomatic table without Trump’s implicit protection.

Europeans stepped in and replaced the United States as Ukraine’s donors. The U.S. now only sells weapons to Ukraine, and even those deliveries are unreliable and have been used as leverage to threaten and badger Kyiv.

This stage in Trump’s incremental betrayal of both Ukraine and the longstanding foreign policy principles of his own country has been punctuated by moments of clearly performative misdirection, which is why some observers lost sight of the direction of travel.

How far could Trump take America toward autocratic superpower status — effectively reversing Washington’s postwar role as the power of pro-democracy leverage in systemic conflicts — and what would that mean for Ukraine?

Every few months, Trump would express irritation with Putin, hint at tougher measures, or float a generous offer to Kyiv, and the media would dutifully announce that he was coming around to Ukraine’s side.

None of the rhetorical generosity translated into concrete aid.

He threatened “crippling” sanctions if Putin continued to reject peace; Putin rejected Trump’s ceasefire proposals and Zelensky accepted them, yet no such sanctions ever followed. He authorized Tomahawk missiles and never supplied them. He dangled a licence for Ukraine to produce Patriot missiles and never granted it. He sold a critical minerals agreement as a quasi-security guarantee, in which America would develop Ukraine’s resources and therefore have a stake in defending them, but when Ukraine resisted a colonial, extractive version of the deal, the Trump administration lost interest.

Real security guarantees never materialized at all. These proposals were smoke and mirrors; headlines for the news cycle and cover for what was really happening.

Now is the second stage, which is the move from bothsiding to an overt thumb on the scale in favour of Russia. An honest broker does not throttle one side’s battlefield capabilities, and it does not hand the other side an economic lifeline. After intelligence sharing, which Ukraine relies on for warnings of incoming ballistic missiles, was paused, Ukrainian officials say Russian strikes landed without the usual advance warning.

Ukraine’s Starlink service, owned by Trump advisor Elon Musk and paid for by Ukraine and its European allies, not by the U.S., was throttled both in the cities where it is needed for drone interception and on the front line, where the Ukrainian military has relied on it to target the logistics supply routes of the Russian military in the occupied Ukrainian territories.

The administration has denied some of this, and access has reportedly been partly restored, but the episode showed that a critical battlefield capability can be switched off from Washington. That makes it not just a pointed reminder, but a means of coercing Ukraine into concessions.

Meanwhile, the administration has waived sanctions on Russia, announced the purchase of Russian diesel, encouraged Europeans to consider unfreezing Russian state assets, and invited Putin to the Miami G20 meeting in December.

Under Trump, America has gone from being the leader of the free world, anchoring NATO with its closest allies, to blatantly transitioning toward the company of rogue actors including China, Russia, North Korea, and, ironically, Iran — the states that keep Russia’s war machine supplied and its economy afloat.

How far could Trump take America toward autocratic superpower status — effectively reversing Washington’s postwar role as the power of pro-democracy leverage in systemic conflicts — and what would that mean for Ukraine?

The United States could lift the remainder of its sanctions on Russia. It could end weapons sales to Ukraine and, in due course, begin selling weapons to Russia. It could share intelligence with Moscow about Ukrainian positions.

If this seems absurd, it is no more absurd in relative terms than what has already happened, and every item on that list fits the logic of what the administration has already done and the motives it has shown. Europe and Canada should plan for these outcomes and not dismiss them as unthinkable.

There is some hope that Democratic majorities in Congress after the midterms could produce a more assertive legislature. But even a Congress determined to act would find that the president retains considerable room to maneuver by executive order, as the latest sanctions waiver shows.

For Ukraine, this means the war must be fought on the assumption that the United States is now an adversary. As Zelensky has spelled out, Ukraine cannot win against a Russo-American alliance.

Ukraine will keep showing up for talks as it is the only party truly interested in peace. But it will not cross its own red lines. Zelensky has been consistent that Ukraine can offer a ceasefire and some form of freezing of the front line, and nothing beyond that.

Russia, meanwhile, has made it clear that it wants far more. In recent days, Russian officials have reiterated their maximalist goals, which include regime change in Kyiv, the loss of Ukrainian external and internal sovereignty, no security guarantees for Ukraine, and Russian participation in decisions about the broader security of Europe. Every item on that list is a non-starter for Ukraine and Europe.

The talks cannot uncover a zone of agreement which clearly doesn’t exist. The war is likely to continue. If Trump is so desperate to continue helping Putin, he’ll have to own the results. Neither Ukraine, nor Europe will make it easy for him by surrendering.

Policy Columnist Maria Popova is the Hiram Mills Associate Professor of Political Science at McGill University and Co-Director of the Jean Monnet Centre Montreal.