Ukraine winning war with Russia, retired U.S. generals say, as top Ukrainian commander says 370 miles retaken

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

They gave that assessment to CBS News as Ukraine’s top general Oleksandr Syrski said this week that his army has retaken 600 square kilometers — about 370 miles — from Russia so far this year. Syrski did not say where the gains occurred but said the fighting was heaviest in the country’s southeast Oleksandrivka and Huliaipole areas.

“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, former director of the Defense Intelligence Agency, said in an email this week.

Two generals agreed with Ashley’s characterization, stressing the view that on the front lines, Ukraine was outmaneuvering Russia.

Military experts say the key factor driving Ukraine’s recent successes is evolutions in its mid-range drone strike capabilities. Since 2023, Ukraine has developed an effective arsenal of short-range First Person View (FPV) drones that now cause more than 90% of Russian casualties, according to Ukraine’s President Volodymyr Zelenskyy. And beginning in 2024, Ukraine has also effectively deployed long-range drones and cruise missiles that have targeted, most recently, military bases in St. Petersburg, more than 600 miles from Ukraine’s borders.

Until recently, finding drones to hit targets reliably between 30-60 miles remained elusive. A front-line R&D unit of Ukraine’s elite Khartiia Brigade told CBS News in March that expanding their drones’ ranges to surveil and hit targets beyond 30 miles was their “top priority.”

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

“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,” Lee 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.”

In a war of attrition where both Ukraine and Russia are attempting to outlast one another’s resources, these mid-range strikes could prove increasingly important for Ukraine. By targeting logistics hubs and resource stockpiles, Ukraine is attacking the systems that sustain 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.”

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

“All of this is reversible and fragile at best depending on how much Putin wants to escalate,” Ashley said.

“The situation has gotten better for Ukraine, but I don’t think we’re going to see a breakthrough,” Lee said.

Retired Gen. Joseph Ralston, a former supreme allied commander in Europe, said he still believed no one is winning the war 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.”

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

“Both sides still see victory, which means no one will entertain a ceasefire anytime soon,” Ashley said. “But time is not necessarily on Putin’s side.”

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