What’s at Play as Trump Encourages Ukraine to Go on Offense

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The US president raised the possibility that Ukraine could reclaim its pre-war territory from Russia.

President Donald Trump voiced a newfound optimism that Ukraine can retake all of its pre-2014 territory from Russia, potentially bolstering Kyiv’s fighting spirit after a costly three-and-a-half years of conflict.

In a speech before the U.N. General Assembly on Sept. 23, Trump signaled willingness to raise pressure on Russia, if his European allies would significantly curb their continuing reliance on Russian energy exports. Later that same day, Trump affirmed that, with enough European support, Ukrainian forces could feasibly retake all the territory they’ve lost to Russia over the years.

Trump had previously raised the possibility of a negotiated settlement that would either freeze the conflict along the current battle lines, or entail some land swaps between Russia and Ukraine.

The U.S. president’s expression of newfound optimism for Ukraine’s battlefield advantage follows months of outreach to Russian President Vladimir Putin, but with little traction toward a cease-fire.

“After getting to know and fully understand the Ukraine/Russia Military and Economic situation and, after seeing the Economic trouble it is causing Russia, I think Ukraine, with the support of the European Union, is in a position to fight and WIN all of Ukraine back in its original form,” Trump wrote in a Sept. 23 post on Truth Social.

While Ukraine winning back all of its territory is a departure from previous Trump administration assessments of this specific conflict, he has previously pushed for Europe to take on greater responsibility for the security of the region.

Moreover, Trump’s comments about the need for European support for Ukraine are consistent with steps he took over the summer to renew the flows of western weapons to Ukraine.

In July, he announced a new security assistance framework with the North Atlantic Treaty Organization, whereby alliance members would purchase military equipment from the United States to provide to Ukraine.

Despite the outside support, Ukrainian efforts to retake territory have seen mixed results thus far.

Late in the summer of 2022, Ukrainian forces wound back some of Russia’s territorial gains. Another Ukrainian counteroffensive, in the summer of 2023, petered out without making a significant dent in Russia’s lines.

By Ryan Morgan

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