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Retired U.S. Generals Say Ukraine Has Upper Hand as Army Reports 600 Square Kilometers Retaken

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Retired U.S. generals assess Ukraine as winning war after 230 square miles retaken

“I would assess operationally Ukraine is winning in the context they are defeating enemy operational objectives, creating conditions for follow-on operations and preserving freedom of action,” retired Lt. Gen. Robert Ashley, a former director of the Defense Intelligence Agency, said in an email to CBS News this week.

Several retired U.S. generals and a former U.S. intelligence chief told the network they think Ukraine now has the upper hand against Russia. Two generals agreed with Ashley’s characterization and said Ukrainian forces were outmaneuvering Russia on the front lines.

The comments came as Ukraine’s top general, Oleksandr Syrski, said his army has retaken 600 square kilometers, about 232 square miles, so far this year. He did not say where the gains were made. The fighting was heaviest, he said, in the Oleksandrivka and Huliaipole areas of the southeast.

Drones behind the shift

Military experts credit Ukraine’s mid-range drone strikes for the recent progress. Since 2023, Ukraine has built up short-range First Person View (FPV) drones that now cause more than 90% of Russian casualties, according to Ukraine’s president. From 2024 it has also used long-range drones and cruise missiles, most recently against military bases in St. Petersburg, more than 600 miles from Ukraine’s borders.

Reliably hitting targets 30 to 60 miles out was the gap. A front-line research and development unit in the elite Khartiia Brigade called extending its drones’ range beyond 30 miles its “top priority.”

Rob Lee, a Ukraine-based military analyst and former U.S. Marine Corps infantry officer, said Ukrainian units have largely solved it. “Ukraine just lacked this capacity last year, the ability to hit targets at 50 to 100 kilometers (30 to 60 miles) past the front line,” he told CBS News. “They’re doing that very often, basically every day now. And the quantities of these drones they’re using is only going to increase.”

The targets are logistics hubs and stockpiles, the systems that feed Russian offensives. “Command posts are getting targeted, warehouses with ammunition, vehicles,” Lee said. “And so over time, it’s going to degrade what gets to the front line.”

Caution from the same experts

Neither Lee nor Ashley called a Ukrainian victory inevitable. “All of this is reversible and fragile at best depending on how much Putin wants to escalate,” Ashley said. Lee put it this way: “The situation has gotten better for Ukraine, but I don’t think we’re going to see a breakthrough.”

Retired Gen. Joseph Ralston, a former supreme allied commander in Europe, disagreed that anyone is ahead. He said no one is winning because “Russia is not strong enough to take all the territory they want without using nukes and Ukraine is not strong enough to take back the territory they have lost.”

Lee and Ashley still argued that recent battlefield trends favor Ukraine. Ashley said both sides still see victory, so nobody will entertain a ceasefire anytime soon. “But time is not necessarily on Putin’s side,” he said.

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