Putin’s Underestimating of Trump Is Among the Mistakes That Could Trigger the End of the Russian Tyrant’s Dictatorship

Putin, too, misjudges the patriotism, toughness, and ingenuity of the Ukrainians.

AP/Alexander Zemlianichenko, file
President Trump shakes hands with President Putin after their meeting at the Presidential Palace, Helsinki, July 16, 2018. AP/Alexander Zemlianichenko, file

Vladimir Putin is making three disastrous mistakes. If he keeps it up, he may bring about the end of his dictatorship.

First, Mr. Putin clearly believed the former chairman of America’s Joint Chiefs, Mark Milley, who said the Russian army could control Kiev in three days. When that failed decisively, Mr. Putin decided he could win a war of attrition. Yet, the Ukrainians did not collapse. 

Instead, they innovated, drove the Russian Black Sea Fleet into total withdrawal, and modernized with weapons given to them by America and European allies. 

Furthermore, American intelligence capabilities and Elon Musk’s diversion of Starlink to provide communications throughout Ukraine became a major game changer. 

Consistently underestimating the patriotism, toughness, and ingenuity of the Ukrainian people was Mr. Putin’s first mistake.

Second, Mr. Putin underestimated Europe’s courage. The Europeans saw his vicious and unprovoked attack on Ukraine. They decided to support Ukraine and genuinely build up their own military capabilities. 

As a friend of mine put it, Mr. Putin managed to resurrect German military capabilities. You would think after 1914 and 1941, this would be the last thing Russia would want.

Russia’s aggression — and President Trump’s warning that America would not always bail Europe out — led Europeans to rise to the occasion. We are now seeing the most serious discussion of rearming and reorganizing the European military since the early 1950s. 

Mr. Putin underestimated the Europeans’ ability to realize his aggression is a direct threat to their own freedom and security.

Putin’s third mistake — and the one which could shatter his dictatorship — is his complete misunderstanding of Mr. Trump. 

Mr. Trump is serious about getting to a ceasefire. He wants to save tens of thousands of Ukrainian and Russian lives. He is also clear about the real dangers of nuclear war and how disastrous one would be.

As someone who has been negotiating his entire life, Mr. Trump has a track record of getting what he wants. Mr. Putin and his advisers should read “The Art of the Deal” and “The Art of the Comeback.” They would get a better sense of how Mr. Trump operates.

So far, Mr. Trump has been nice to Mr. Putin and his team because he wants them at the table negotiating. If you can’t get the other guy to the table, you can’t get a deal. Posturing, maneuvering, minor offers, stubbornness, and delay tactics are all part of the dance.

However, Mr. Putin’s position is about to crumble. His conditions for a truce are really the conditions for Ukrainian surrender. Mr. Putin promises temporary cease fires on certain targets — and then aggressively attacks them harder than ever. 

He is clearly testing Mr. Trump to see if his desire for a ceasefire would lead him to accept a settlement which inevitably would lead to Ukraine’s collapse.

Mr. Putin has confused Mr. Trump’s patience for weakness. As a result, Mr. Putin is risking a direct and stunning response from an increasingly angry American President.

The more openly dishonest, hostile, and aggressive Mr. Putin gets, the more endangered his rule becomes. Mr. Trump may conclude that he must defeat Mr. Putin rather than negotiate with him.

If Mr. Trump decides he needs to get Mr. Putin’s attention (something he clearly does not have) it will be amazing to see the wide range of economic, psychological, diplomatic, and possibly kinetic tools he can bring to bear. 

Mr. Putin may soon realize there is no alternative to working with America if he wants to keep his power. He will ultimately have to agree to a truce which guarantees a free, prosperous, and independent Ukraine with major national security safeguards. 

Then he will have to learn from his mistakes – while trying to keep his dictatorship.


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