A Tale of Competing Agendas on Ukraine: Will history judge Trump as a Churchill or a Chamberlain?

By Rob Dannenberg

Rob Dannenberg served as chief of operations for CIA's Counterterrorism Center, chief of the Central Eurasia Division and chief of the Information Operations Center before retiring from the Agency.  He served as managing director and head of the Office of Global Security for Goldman Sachs, and as director of International Security Affairs at BP.  He is now an independent consultant on geopolitical and security risk.

OPINION / EXPERT PERPSECTIVE — In coming weeks, President Trump will meet with Ukrainian President Volodymyr Zelensky and after that meeting, with Russian President Vladimir Putin in an effort to make good on his campaign promise to end Russia’s war in Ukraine. 

The outcome of these meetings will be watched closely by what’s left of the ‘Axis of Resistance’, by the People’s Republic of China, and other nations that are closely or tenuously aligned with the anti-western coalition that President Putin has orchestrated and led since at least 2008.

The results will also be closely watched by U.S. allies in the West and around the globe who are looking for a signal as to whether the second Trump administration is more representative of what history remembers of British Prime Minister Winston Churchill, who led his country to victory in World War II, or British Prime Minister Neville Chamberlain, who upheld a policy of appeasement toward Nazi Germany during his time in office from 1937-1940.

While the Trump administration still has not announced details about where or when a meeting with the Russian president may take place, it’s a good sign that it will not happen before the U.S. president meets with President Zelensky.  Meanwhile, Russian sources are suggesting that the Trump-Putin meeting will include discussion of nuclear arms control, global energy prices, the situation in the Middle East, and Trump’s stated aim to bring a swift end to the Ukraine war (those paying close attention will note the use of the term ‘war’ rather than ‘Special Military Operation’ which is what the Russian have been calling their barbaric actions in Ukraine for the past three years.


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To an experienced Russia hand, the other issues on the agenda take a distant second place to discussions meant to bring about an end to the war in Ukraine. Clearly, no serious negotiations can take place without the participation of Ukraine at every level, but the sequence of Trump-Zelensky followed by Trump-Putin can help pave the way to a better outcome. 

Trump and Zelensky could meet in Washington in the coming days. Certain to be on Zelensky’s agenda is a review of Kyiv’s own plan to end the war. High on Trump’s agenda is certain to be his expressed desire to bring a quick end to the war in a deal tied to future U.S. aid to Ukraine and granting access to Ukrainian reserves of precious and critical mineral resources – some deposits of which lie in Russian-occupied Ukrainian territory. 

A transactional agreement with Ukraine on continued U.S. support is certainly a commendable and achievable objective.  But the most important result of the Trump-Zelensky meeting must be the clear messaging to Putin that he is entering negotiations from a position of weakness and that U.S. and Western support for Ukraine is not on the negotiating table. Anything short of this will lead Putin to believe that he is dealing with a 21st century Neville Chamberlain.

Putin will be well prepared for his first meeting and will remember Trump’s lack of preparation and failure to bring aides or notetakers to their private meeting in Helsinki in 2018. Other than the two Presidents, the only other attendee was a Russian-provided interpreter.

This was a mistake and should not be repeated.

As a trained former operations officer, the Russian President is experienced and detail oriented. His preparations will certainly include messaging designed to play on what he believes to be weaknesses in Trump’s character and ego. 


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Putin may or may not have accurate targeting information on the U.S. President, but it will be to the advantage of the free world if the Trump team is prepared and clearly signals to Putin that he is entering the meeting in a weak negotiating position and is dealing with a confident U.S. administration that is prepared to resume its position as the leader of the free world. He will be meeting with a 21st century reincarnation of Winston Churchill in the form of his willingness to stand up to totalitarian aggression.  Churchill’s messaging to Hitler was unequivocal, inspirational to his Allies and as a result, he is remembered with admiration by history.

What we see on the battlefield tells us that the Russian president is still willing to expend Russian manpower and capital in the failed invasion of Ukraine. Putin’s objective for the war remains largely unchanged. He wants a “neutral” (subservient) Ukraine.  Putin’s understanding of Ukraine is ahistorical and unrealistic—unless the U.S. and West allow him to succeed in his ambition.  The sooner and stronger the Trump team asserts a new reality to Putin the better.

Clearly, Moscow has not yet received the message. Russian Deputy Foreign Minister Sergei Ryabkov recently said about Ukraine, “the political solution we envisage cannot be achieved otherwise than through the full implementation of what was pronounced by President Putin when he spoke to the Russian Foreign Ministry in June.” 

In Putin’s June speech, he said Kyiv must renounce all NATO ambitions and withdraw all troops from four Ukrainian regions that Russia has partially occupied and claims it annexed. The Biden Administration should have responded to that speech in June 2024 (or at any time since the invasion began) by stating U.S. conditions for end of the war including Russian withdrawal from all Ukrainian territory, payment of reparations for war damages and remanding war criminals to international justice.


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We missed that opportunity during the years the Biden administration managed the war and as a result, we left Russia in a position to complicate negotiations to end the war as Ryabkov’s statement suggests. Russia loves to negotiate (however much in bad faith) when it believes it has the advantage.

Putin will also want an end to western sanctions and a resumption of European addiction to Russian hydrocarbons.  Allowing this to happen would be a mistake of historic proportions. Europe is on a path toward building alternative sources of energy, rebuilding its defense capabilities, and living up to its NATO commitments. Europe’s current path is a direct consequence of Putin’s strategic mistakes, as are the decisions by Sweden and Finland to join NATO. This momentum toward a modern and less U.S.-centric containment of Putin should be encouraged and reinforced.

Both sides need this war to end. The Ukraine cannot indefinitely sustain the losses of the Russian strategy of attrition. Russia cannot indefinitely continue to be isolated from the world’s economy, endure continued inflation and high interest rates with the loss of foreign investment and energy revenues. 

Russia under Putin is working its way back to a third-world economy. The pillars of Putin’s overseas support – Syria and Iran – have experience regime change or strategic humiliation in recent months. China must be questioning the sensibility of their ‘partnership without limits’ with Russia. 

The destruction and loss this war has caused are solely Putin’s responsibility and Russia needs to bear the full price for starting this war. If the Trump teams sells Ukraine short by negotiating a deal to get “peace in our time” as Chamberlain did in Czechoslovakia in 1938, it will be remembered in equal infamy as Chamberlain and the Munich agreement. 

We are rapidly approaching a binary moment in world history:  Churchill or Chamberlain?  The world is watching.

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