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Trump is failing Ukraine — that will only change if he gets tough on Putin

September 30, 2025
in News, Opinion
Trump is failing Ukraine — that will only change if he gets tough on Putin
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Fredrik Wesslau is a distinguished policy fellow at the Stockholm Centre for Eastern European Studies and Senior Adviser at Rasmussen Global. He was previously deputy head of the EU Advisory Mission in Ukraine.

U.S. President Donald Trump’s efforts to stop the war in Ukraine have been a failure — though not for lack of trying: He has spoken to Russian President Vladimir Putin on the phone at least seven times since the start of the year, sent his Special Envoy Steve Witkoff to meet the Russian leader five times and organized a lavish red-carpet summit in Alaska, all to no avail.

Now, it seems the U.S. president has belatedly realized his efforts have gone nowhere because of Putin himself. During the United Nations General Assembly last week, Trump finally aired his frustrations, posting on Truth Social that Russia was a “paper tiger” and that Ukraine could take back all territories conquered by Russia.

Of course, it remains to be seen whether Trump is willing to back these unusually strong words with actual measures. But so far, his efforts to secure a ceasefire have made peace a more distant prospect. This is because, for whatever reason, Trump is completely unwilling to apply any pressure on Russia.

As he was overheard telling French President Emmanuel Macron in the White House, Trump believes Putin wants to make a deal with him. And though he isn’t willing to press Putin, escalatory measures may well be the only way to make this happen.

Rather than draw Moscow to the negotiation table, Trump’s unwillingness has only emboldened Putin, as he sees little risk of retaliation. Putin is essentially following Vladimir Lenin’s dictum: “You probe with bayonets: If you find mush, you push. If you find steel, you withdraw.”

And in Trump, Putin has found mush.

Only recently, the U.S. president’s reticence was visible in his equivocal reaction to Russia’s violation of NATO ally Poland’s airspace with at least 20 drones, saying it “could have been a mistake” despite strong indications otherwise. Even when telling NATO allies to shoot down Russian aircraft violating their airspace while at UNGA, he still questioned whether the drones over Denmark were Russian.

If Moscow is testing Trump’s reaction, surely it must be pleased.

On numerous occasions, he has threatened sanctions against Russia, but these threats have turned out to be hollow. Deadlines have come and gone without consequence, and Putin has been skillful at throwing Trump a bone just juicy enough to avoid punishment — though without any real meat.

Now, Trump is conditioning new sanctions and tariffs against Russia on Hungary and Slovakia halting their imports of Russian gas. But while this may usefully firm up Europe’s posture toward Russia, it seems more like a diversion for Trump to avoid imposing new sanctions.

In all of this, Moscow has, of course, taken note of how the U.S. leader shies away from exerting any real pressure. It’s the sort of weakness the Kremlin both loathes and is a master at exploiting. The question is, whether Trump’s newly found hawkishness is just rhetorical.

Putin, for his part, has little interest in a ceasefire. He believes his forces are slowly but surely grinding down Ukraine’s defenses, and that the West’s support for Kyiv will wane over time. He thinks Russia will eventually achieve its objectives on the battlefield — notwithstanding the high cost in manpower and material. And if there’s a deal to be made, he believes the longer he holds out, the better the terms will be.

So, absent any real prospect of U.S. pressure, he has been escalating the war: Since May, Russia launched several massive drone and missile attacks on Kyiv and other Ukrainian cities. The past few weeks saw Moscow targeting “decision-making centers” and no longer caring if foreign embassies are damaged in the strikes. Then, on Sept. 7, Russia carried out its largest attack on Kyiv to date with over 800 drones, including a strike on the Cabinet of Ministers building where Ukraine’s prime minister works.

If Trump is serious about a ceasefire, he needs to finally turn the screws on Russia in order to change the calculation in Moscow. Putin should be made to see he has more to gain from a ceasefire than from war. And by escalating in this way, Trump could achieve de-escalation. The West could do this through the imposition of hard-hitting sanctions — notably secondary sanctions — on energy exports and on the Russian shadow fleet, as well as seizing of the €300 billion in frozen Russian assets.

Next, military assistance to Ukraine should increase in both quantity and quality. The country needs deep-strike capabilities and the green light to use them against military targets in Russia.

Then, capitalizing on the work done on security guarantees, Europe and the U.S. should together seize the strategic initiative and deploy an air-policing operation to western Ukraine — even before a ceasefire.

Such an operation should be integrated into Ukraine’s air defenses, helping defend it from Russia’s massive drone and missile attacks. Land-based air defense systems in frontline countries like Poland and Romania could also be used to intercept Russian drones and missiles over Ukraine before they reach the airspace of NATO allies — the incursion into Polish airspace shows just how much NATO needs to enhance its counter-drone capabilities if it is to credibly deter Russia.

Finally, NATO allies should send troops to Ukraine in noncombat supportive roles, such as training, intelligence and logistics, which would show they’re ready to put more skin in the game.

Such measures would send a strong signal to Moscow that the U.S. and Europe are ready to ramp up pressure on Russia — and it might just suffice to move Putin toward a ceasefire.

The post Trump is failing Ukraine — that will only change if he gets tough on Putin appeared first on Politico.

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