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The Daily

Inside Putin’s Plan to Cripple Ukraine This Winter

October 19, 2026 • 29m

Summary

⏱️ 9 min read

Overview

This episode examines the deteriorating relationship between the United States and Ukraine, as President Trump publicly feuds with President Zelensky while Russia launches one of its most devastating bombing campaigns of the war. The episode explores Russia's strategic winter offensive targeting civilian infrastructure, Ukraine's vulnerability due to limited air defenses, and the potential consequences of reduced American support as Moscow attempts to bomb Ukraine into submission.

The Collapse of U.S.-Ukraine Relations

The past week has marked one of the worst periods in the U.S.-Ukraine relationship since the war began over four years ago. Following Trump's diesel deal with Putin, public exchanges between Trump and Zelensky have turned hostile, with Trump blaming Zelensky for the war's continuation and even suggesting Ukraine should elect a new president. Zelensky initially tried to maintain calm but eventually expressed feeling betrayed, stating that Trump prefers striking business deals with Moscow and has an affinity for autocrats.

  • Trump publicly blamed Zelensky for the current state of the war and the diesel crisis, suggesting Ukraine should vote him out of office
  • Zelensky initially attempted to maintain calm but eventually said Trump prefers business deals with Moscow and has an affinity for autocrats
  • The public feud comes as Russia expands its bombing campaign, sending salvos of missiles and drones every other night
" I think it's time for Ukraine to get a new president. "
" Do you feel betrayed by what has been happening? Really yes, really between us. "

Russia's Devastating Bombing Campaign

Russia has dramatically escalated its attacks on Ukraine, launching some of the most severe bombing campaigns of the entire war. In the first week of October alone, Russia sent dozens of missiles and hundreds of drones in single attacks, killing more than 100 civilians—a level of casualties not seen since the war's first month. The shift is particularly notable because while the front lines have stabilized, cities like Kyiv that are hundreds of miles from combat have become far more dangerous.

  • Russia is sending dozens of missiles and hundreds of drones in single overnight attacks, also targeting Ukraine during the day
  • More than 100 civilians were killed in just the first week of October, among the highest casualty rates since the war's first month
  • While Ukrainian forces have stopped Russian advances at the front, cities far from combat have become significantly more dangerous
" For years you didn't really feel the war that much in cities away from the front. And now it's almost the complete opposite. Things are actually going pretty well for Ukraine at the front because they've managed to stop the Russian advances. But further back, behind the front in cities like Kyiv, Odessa, things have become way more dangerous. "

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