The conversation opens with a reflection on how the Russia-Ukraine war can appear, at a glance, to have devolved into a financial and bureaucratic contest—focused on who’s spending the most, hiring the most contractors, or making the best deals. But the reality remains: there is still a brutal war occurring, with real human cost, suffering, and military progress on the ground.

Dr. Gilbert Doctorow, historian and author of War Diaries Part One: Russia-Ukraine War 2022–2023, joins Daniel Davis to give insight into how the war unfolded and how the West has misunderstood many of its elements.

Key Points:

Initial Expectations and Misjudgments:

Most analysts (including the author) expected the war to end quickly, given Russia’s initial advantage.

Russia did not conduct a "shock and awe" campaign like the U.S. typically does; instead, it tried to limit damage and casualties, assuming it would eventually have to live peacefully with Ukrainians again.

This restraint was mistaken in the West as weakness.

Western vs. Russian Military Thinking:

Western wars, especially in the Middle East, often lacked cultural ties or concern for civilian life.

In contrast, Russia and Ukraine share centuries of familial, cultural, and historical ties, which influenced early Russian military conduct.

2014 and the Crimea Precedent:

In 2014, during the Crimea standoff, Ukrainian troops largely surrendered or defected.

Russia expected a similar reaction in 2022, misjudging how much the Ukrainian military had changed, especially due to U.S. and UK training and ideological hardening.

Ukrainian Resistance:

By 2022, Ukraine had a motivated and ideologically-driven military, with radical nationalist elements like the Azov Battalion integrated into its formal forces.

These changes made a quick Russian victory impossible.

Intelligence Failures:

Russia significantly underestimated Ukrainian resistance.

The U.S. overestimated how quickly Russia would take over.

Peace Talks and Zelensky’s Position:

Early on, Zelensky publicly entertained the idea of neutrality (non-NATO status), which was Russia’s core demand.

Negotiations in Belarus and Istanbul showed promise, with draft agreements emerging by April 2022.

However, Zelensky’s position soon hardened, possibly due to Western influence, and meaningful talks stalled.

Dr. Doctorow expresses skepticism about taking Zelensky’s statements at face value, suggesting political maneuvering.

About the Book:

War Diaries is not a conventional military history but a personal journalistic account.

It includes rare insights from trips to Russia during the war—a period when most Western journalists had left due to COVID or legal fears.

Doctorow had access via a humanitarian visa (his wife is Russian), giving him a unique on-the-ground perspective.

Conclusion:

The war has been deeply misunderstood in the West due to assumptions about how wars are fought, underestimation of Russia’s strategy, and overreliance on propaganda. Doctorow’s book offers a ground-level narrative of how those expectations clashed with the messy, prolonged, and politically complex reality of the war.

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