The CIA and Ukraine A Covert Alliance Reshaping Modern Conflict

In this episode of the War Lab, hosts trace the once‑covert, now pivotal alliance between the U.S. Central Intelligence Agency and Ukraine’s intelligence services—an evolving partnership that has shaped Kyiv’s ability to withstand Russian aggression since 2014. Beginning with the Maidan uprising’s aftermath, when a shattered SBU (Ukraine’s domestic spy agency) lay exposed and penetrated, Ukraine’s leadership appealed directly to the CIA and MI6 for help rebuilding its capabilities from the ground up .

The discussion then explores early Western reluctance—rooted in fears of political instability, past betrayals, and self‑imposed “red lines” against lethal support—and how Kyiv overcame these barriers by delivering high‑value intelligence on Russian naval and nuclear programs. Key milestones include the 2016 “Scattergood” agreement formalizing intelligence‑sharing; the creation of Operation Goldfish; and the training of elite units (HUR and Unit 2245) to capture and reverse‑engineer Russian drones and comms gear, revealing the dual‑use nature of covert skills.

Under the Trump administration, despite mixed public signals, CIA‑Ukraine cooperation deepened: encrypted radios, advanced SIGINT tools, and clandestine training in European safe houses transformed Ukrainian operatives into modern intelligence professionals. The episode highlights the dramatic construction of a dozen secret, subterranean forward bases along Ukraine’s eastern border—fully financed and partially equipped by the CIA—to intercept, decrypt, and analyze Russian communications in real time.

As tensions escalated toward the full‑scale invasion in February 2022, Biden’s team strategically retained CIA officers in western Ukraine, ensuring an unbroken flow of tip‑of‑the‑spear intelligence. Early warnings—of strikes on humanitarian corridors, amphibious assaults on Odessa, and assassination plots against President Zelensky—proved decisive, enabling Kyiv to preempt or blunt Russian operations. Once the invasion began, previous handcuffs were removed: U.S. agencies were formally cleared to support lethal targeting, solidifying a partnership born of necessity.

The hosts reflect on the friction inherent in this relationship: Washington’s caution versus Kyiv’s “better to beg forgiveness than ask permission” ethos, which spurred unilateral Ukrainian raids deep into Russia and targeted assassinations that infuriated U.S. officials but demonstrated Ukraine’s resolve. Yet, despite outrage at breached red lines, CIA Director Brennan argued—and ultimately prevailed—that the strategic intelligence value outweighed the political costs.

Finally, the episode situates this modern alliance against the backdrop of Cold War lessons—most notably the disastrous Operation Red Sox—and shows how today’s robust, battle‑hardened Ukrainian forces, backed by overt Western aid, differ fundamentally from unsupported insurgents of the past. Listeners are left considering how the public disclosure of once‑classified operations reshapes deterrence psychology: by weaponizing transparency, the West signals to adversaries that its covert partnerships are both deep and unbreakable.