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Ukraine is winning the war with Russia, retired US generals say, as Ukraine’s top commander claims 370 miles back

Kyiv – Several retired US generals and a former director of the US intelligence agency told CBS News that they believe Ukraine now has the upper hand in the war with Russia.

They gave that assessment to CBS News as Ukraine’s top commander Oleksandr Syrski said this week that his army has taken 600 square kilometers – about 370 miles – from Russia so far this year. Syrski did not say where this success took place, but he said that the battle was more difficult in the south-eastern areas of the country, Oleksandrivka and Huliaipole.

“I will check that Ukraine succeeds in the situation where it defeats the enemy’s operational objectives, creates conditions for the continuation of operations and maintains freedom of action,” said Lt. General Robert Ashley, former director of the Defense Intelligence Agency, in an email this week.

The two generals agreed with Ashley’s interpretation, emphasizing the view that on the front lines, Ukraine was defeating Russia.

Ukrainian soldiers fire artillery at Russian positions in Donetsk Oblast, Ukraine, on May 31, 2026.

Diego Herrera Carcedo/Anadolu via Getty Images


Military experts say a key factor driving Ukraine’s recent success is the emergence of its medium-range drone strike capabilities. As of 2023, Ukraine has established an active fleet of short-range First Person View (FPV) aircraft that now account for more than 90% of Russian casualties, according to the President of Ukraine. Volodymyr Zelenskyy. And since 2024, Ukraine has also successfully fielded long-range drones and cruise missiles targeting, most recently, military bases in St. Petersburg, more than 600 miles from the Ukrainian border.

Until recently, getting drones to reliably hit targets between 30-60 miles has been impossible. The flagship R&D unit of Ukraine’s Khartiia Brigade he told CBS News in March that expanding the range of their drones to explore and reach targets beyond 30 miles was “their top priority.”

Rob Lee, a Ukraine-based military analyst and former US Marine Corps infantry officer, said Ukrainian units have now largely solved the problem.

“Ukraine just lacked this capacity last year, the ability to score 50 to 100 kilometers (30 to 60 miles) past the front line,” Lee told CBS News. “They’re doing that more often, basically every day now. And the number of these drones they’re using is only going to increase.”

In a war where Ukraine and Russia are trying to outflank each other’s resources, these medium-range strikes would prove to be very important to Ukraine. By targeting logistics hubs and resource depots, Ukraine attacks the systems that support Russian attacks.

“Command posts are targeted, warehouses with ammunition, vehicles,” Lee said. “And in the long run, it’s going to degrade what comes forward.”

However, both Lee and Ashley cautioned against conflating Ukraine’s operational success with inevitable strategic victory.

“This is all reversible and very fragile depending on how much Putin wants to expand,” Ashley said.

“The situation has improved in Ukraine, but I don’t think we will see success,” said Lee.

Retired General Joseph Ralston, who was the commander of the coalition in Europe, said that he still believes that no one wins the war because “Russia is not strong enough to take all the territory it wants without using nukes and Ukraine is not strong enough to recover the territory it lost.”

Still, both Lee and Ashley argue that recent trends on the battlefield suggest that Ukraine has the upper hand.

“Both sides still see a win, which means no one is going to be happy about ending the conflict anytime soon,” Ashley said. “But time is not on Putin’s side.”

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