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Ukraine winning war with Russia, retired U.S. generals say, as top Ukrainian commander says over 230 square miles retaken

Published June 10, 2026 · Updated June 10, 2026 · By Matthew Garcia

Ukraine Winning War Against Russia: Ex-Defense Officials Weigh In

Ukraine winning war with Russia retired - Ukraine winning war with Russia is gaining momentum, according to insights from retired U.S. military leaders and a former intelligence director. This analysis highlights a pivotal shift in the conflict as Ukrainian forces continue to assert control over key territories. Top Ukrainian commander Oleksandr Syrski recently confirmed that more than 230 square miles have been reclaimed from Russian positions, signaling a strategic turning point. However, Syrski emphasized that the most intense battles remain concentrated in areas like Oleksandrivka and Huliaipole, underscoring the ongoing challenges in the southeastern front.

Expert Perspectives on Tactical Success

Retired Lt. Gen. Robert Ashley, who previously directed the Defense Intelligence Agency, reinforced the notion that Ukraine is on the path to victory. In an email to CBS News, Ashley noted that the nation’s ability to neutralize Russian objectives and maintain military flexibility is a testament to its growing strength. Two other senior U.S. officials echoed this sentiment, stating that Ukrainian troops are now outmaneuvering Russian forces in critical engagements. These assessments provide a broader view of Ukraine’s strategic progress, though they are tempered by the need for sustained effort.

While the optimism is strong, experts caution that Ukraine winning war with Russia remains a work in progress. Rob Lee, a military analyst and former U.S. Marine Corps officer, pointed out that operational victories do not always translate to a decisive outcome. “These gains are significant, but they don’t yet guarantee a long-term strategic win,” Lee said. His analysis underscores the importance of maintaining momentum and adapting tactics to ensure continued success.

Drone Technology as a Game-Changer

Ukraine winning war with Russia has been heavily influenced by advancements in drone warfare. Since 2023, the nation has refined its use of short-range First Person View (FPV) drones, which now account for over 90% of Russian casualties, according to President Volodymyr Zelenskyy. These drones, capable of targeting enemy positions within 30–60 miles, have transformed the battlefield by enabling precision strikes. However, their impact has been limited by the challenge of reaching further targets.

Until early this year, Ukraine’s frontline research teams struggled to extend drone range beyond 30 miles. A source from the Khartiia Brigade, an elite unit, revealed that increasing the operational range was their primary objective. “This was our top priority,” the unit described, highlighting the urgency of developing mid-range strike capabilities. With recent breakthroughs, Ukraine has now achieved the ability to strike targets up to 100 kilometers away, a development that has reshaped the dynamics of the conflict.

Strategic Impact on Logistical Networks

Experts argue that Ukraine winning war with Russia is now centered on disrupting Russia’s supply chains. By targeting critical infrastructure such as supply depots and ammunition warehouses, Ukrainian forces are weakening the logistical backbone of Russian operations. Rob Lee noted that these strikes are degrading the flow of resources to the front line, forcing Russia to reallocate troops and supplies to defend its lines. This has created a more precarious situation for the Russian war effort.

Ukraine’s focus on mid-range drones and cruise missiles has allowed it to conduct deep strikes on enemy positions, a departure from earlier defensive strategies. The ability to attack further into Russian territory has forced the enemy to divert attention from its main objectives. Analysts suggest that this shift is not only improving Ukraine’s chances but also altering the balance of power in the region. However, the war’s outcome still hinges on the nation’s capacity to sustain these operations.

Caution in the Face of Progress

Despite the positive outlook, some military experts remain cautious. Retired Gen. Joseph Ralston, former supreme allied commander in Europe, noted that “no one is winning this war yet.” He emphasized that Ukraine’s advances are still part of an attritional struggle, where both sides are investing heavily in resources. Ralston warned that while Ukraine winning war with Russia has seen tangible gains, the potential for Russia to escalate with nuclear weapons or other measures remains a critical factor.

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