With Russia’s unrelenting war on Ukraine stretching into its 44th month, President Donald Trump warned over the weekend that he is considering sending long-range Tomahawk missiles to Ukraine that could reach targets deep within Russia if Vladimir Putin continues to press the war. Experts say the move could heighten pressure on Putin to deescalate the conflict but also carries with it numerous risks and uncertainties.

On Sunday, Trump told reporters aboard Air Force One, “I might say, ‘Look: if this war is not going to get settled, I’m going to send them Tomahawks.’ … We may not, but we may do it. I think it’s appropriate to bring up.” Ukrainian President Volodymyr Zelensky confirmed that he and the U.S. were discussing receiving the long-range missiles, which have the capability of striking targets deep within Russia. He described his latest call with Trump as “very productive,” discussing “air defense, resilience, and long-range capabilities” as well as “details related to the energy sector.” As to whether Tomahawks were discussed specifically, Zelensky remarked, “I’m waiting for president to [say] yes. Of course, we count on such decisions, but we will see.”

In the meantime, Russia is continuing to target Ukraine’s energy infrastructure ahead of the approaching winter season. CNN reported last week that Putin’s regime is carrying out daily attacks on “energy generating facilities, including gas production and distribution.”

At the same time, current assessments of Russia’s war of aggression calculate that Moscow is continuing to make territorial gains on the Ukrainian front lines at a snail’s pace but is losing vast amounts of soldiers in order to do so. As reported by Politico, Russia suffered over a quarter of a million casualties in just the first eight months of 2025 according to Ukrainian intelligence, including 86,744 killed, 33,966 missing, 158,529 wounded, and 2,311 captured. Overall, it is estimated that Moscow has suffered one million dead, wounded, and missing since it launched its invasion of Ukraine in February 2022. Kyiv has reportedly lost 46,000 soldiers with 390,000 wounded.

As the war approaches its fourth year, Ukraine is reportedly having some success by conducting drone warfare. The New York Times reported Monday that Ukrainian operators stationed well outside of the combat zone are successfully launching explosive drones into Russia that are destroying oil refineries in a bid to interrupt Putin’s energy infrastructure and dampen ordinary Russians’ enthusiasm for the war. In addition, Ukraine is also targeting individual Russian soldiers with drones as Moscow continues its “meat wave” tactic of sending swarms of poorly trained and equipped troops towards the front lines in an attempt to overwhelm opposition forces, which has resulted in a staggeringly high number of Russian casualties. One assessment from June 2025 estimated that Putin was losing “roughly 8,400–10,500 personnel per month as killed in action.”

Still, the latest battlefield assessment found that Russia has gained 3,561 square kilometers of Ukrainian territory so far this year.

Experts like Lt. Col. (Ret.) Bob Maginnis, who serves as senior fellow for National Security at Family Research Council, say that there are some strategic advantages to Trump’s threat of supplying Kyiv with long-range missiles.

“The threat is partly psychological,” he told The Washington Stand. “By telegraphing a willingness to provide Ukraine with long-range strike capability, Trump would change the expected costs for Russia. Putin would have to reassess whether continued escalation will further expose Russian rear areas and installations. If Ukraine can strike deeper into Russian territory (with U.S. equipment), then the war’s battlefield geography changes; that might force Russia to divert air defenses, logistics, etc., and thus increase pressure.”

Maginnis further contended that “if Russia believes there’s a credible risk of deeper strikes, that might sharpen incentives to negotiate (or at least pause) to avoid additional damage.” In addition, “Zelensky has signaled that long-range precision strike tools are essential if Ukraine is to extend pain into Russian territory, not just absorb Russian fire. Trump’s posture may meet that demand.”

“But the strategy has serious downsides and risks,” Maginnis warned. “A repeated threat is only credible if the U.S. is prepared to follow through. If U.S. forces or intelligence do not support or enable Ukraine’s use of such weapons (or if Congress balks), the threat becomes empty and loses leverage.”

He went on to note that the escalation may prove dangerous. “Russia may interpret deployment or use of Tomahawks (or equivalent long-range missiles) as U.S. direct involvement. Kremlin voices already warn of ‘new levels of escalation.’” Additionally, “Russia has frequently used vague nuclear threats to raise the cost of Western supplies for Ukraine. The addition of U.S.-enabled deep strike power might push Russia to more aggressive nuclear signaling.”

Maginnis also observed that equipping Ukraine with Tomahawks could incur collateral damage and is politically risky. “If a strike misses or hits unintended targets, Russia will exploit that for diplomatic and propaganda advantage. Also, U.S. domestic and congressional politics may not support an open escalation. Also, Putin may see this as yet another measure that can be absorbed or met with countermeasures. If his interest is regime survival and prestige rather than ‘winning territory,’ he may dig in rather than yield.”

“Given these factors, the Tomahawk threat is a high-risk, high-uncertainty lever,” Maginnis concluded. “It might achieve marginal gains but also could backfire or be ignored by Putin. It is not, by itself, a sound primary strategy — more an escalation option among others. But it is defensible as part of a larger coercive posture — provided the U.S. still holds reserve options, maintains credibility, and manages escalation carefully.”