Badass or Risky? Trump’s Ukraine Dilemma

President Trump acknowledges Ukraine’s “badass” drone assault on Russian bombers while still pursuing a ceasefire despite pushback from Putin.
At a Glance
- Trump privately praised Ukraine’s Operation Spiderweb as “strong” and “badass” despite previous skepticism of Ukraine’s military capabilities
- The Ukrainian drone attack destroyed over 40 Russian aircraft, causing an estimated $7 billion in damage
- During a recent hour-long call with Putin, Trump was warned that Russia would respond to Ukraine’s airfield attacks
- Trump remains focused on achieving a ceasefire despite the recent escalation
- Putin has ruled out a comprehensive ceasefire while Ukraine’s Zelenskyy dismisses Russian peace proposals as ultimatums
Trump’s Surprising Praise for Ukraine’s Military Strategy
In a notable shift from his previous stance, President Donald Trump has privately expressed admiration for Ukraine’s recent drone attacks against Russian military targets. The operation, codenamed “Spiderweb” and executed by Ukraine’s secret service (SBU), successfully targeted and destroyed dozens of Russian strategic bombers at multiple airbases. This marks a significant departure from Trump’s earlier criticism of Ukrainian President Volodymyr Zelensky, whom he had previously accused of lacking strategic options against Russia’s military might.
According to multiple sources, Trump has described the Ukrainian operation as “pretty strong” and “badass” in private conversations. The successful attack has apparently influenced Trump’s opinion of Zelensky, portraying Ukraine as more capable and Russia as less dominant than previously believed. The operation’s success in targeting strategic bombers, which form a key component of Russia’s nuclear deterrence capability, has garnered recognition not only from Trump but also from NATO allies.
Russia launched another wave of drone attacks on ukraine, striking kyiv for the third night in a row.
This came just after u.s. president donald trump criticized vladimir putin, saying he’s “gone crazy” and warning that trying to take all of ukraine would lead to russia’s… https://t.co/WEBhngAZBi pic.twitter.com/EDjLOquqLi— Eagle News Feed (@eagle_feed) May 26, 2025
Putin Warns of Retaliation During Hour-Long Call with Trump
Despite his admiration for Ukraine’s military success, Trump’s focus remains fixed on brokering a ceasefire between Russia and Ukraine. In a recent hour-long conversation with Russian President Vladimir Putin, Trump discussed the drone attacks on Russian airfields among other ongoing hostilities. Following the call, Trump acknowledged that their talk would not lead “to immediate peace” in Ukraine and warned that Russia would respond to Ukraine’s successful attacks.
“It was a good conversation, but not a conversation that will lead to immediate Peace. President Putin did say, and very strongly, that he will have to respond to the recent attack on the airfields.”, said President Trump.
Trump did not discourage Putin from retaliating against Ukraine for the drone strikes, raising concerns about potential escalation. During the call, Putin reportedly ruled out a comprehensive ceasefire in Ukraine, while Trump has been informed that Zelensky has dismissed Russia’s peace proposals as ultimatums rather than genuine offers for resolution. This deadlock presents a significant challenge to Trump’s stated goal of quickly ending the conflict.
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Balancing Praise with Peace Efforts
The tension between Trump’s admiration for Ukraine’s military achievement and his desire for a quick resolution to the conflict illustrates the complex position he now faces. Sources close to Trump indicate that while he appreciates the strategic success of Operation Spiderweb, he remains concerned that such actions could complicate his efforts to broker peace. Ukraine claims the attack caused approximately $7 billion in damage to Russian long-range bombers, significantly impacting Moscow’s strategic bombing capability.
While negotiations in Istanbul have made no progress toward a comprehensive truce, there has been movement on prisoner exchanges and the potential return of abducted Ukrainian children. Russia is reportedly working on the return of over 300 Ukrainian children, with a prisoner exchange expected soon. European countries have also taken a more active role in supporting Ukraine’s defense, with new military support measures announced at a recent NATO meeting. These developments occur against the backdrop of Turkey’s proposal for a summit involving Putin, Zelensky, and Trump—though Putin has opposed a personal meeting with Zelensky.