OPINION — Is anyone surprised that Russian President Vladimir Putin so badly overestimated his ability to continue to string along U.S. President Donald Trump? Shocked that Putin has once again become the victim of the echo chamber that he created for himself? Is anyone really surprised that Putin, who so badly miscalculated in February 2022 when he launched his full-scale invasion of Ukraine, has again made a serious strategic mistake by failing to take openings offered to him by the U.S. President to end the war in Ukraine?
Putin's failures are actually years in the making. After assuming power in the early 2000’s, he surrounded himself with sycophants and “loyal” servants who were unwilling to give him bad news, and always ready to repeat the lies and distortions the Russian leader wanted to promote. Anyone who dared disagree with him was either thrown in jail, forced into exile or assassinated by the Russian “strongman”.
As a result, in the run up to Putin’s failed February 2022 effort to seize all of Ukraine, there is little doubt that his advisors parroted back to him the things he wanted to hear. I can imagine what that sounded like. “The Ukrainian people love Russia and will welcome Russian forces invading their country with ‘Bread and Salt’;” “Ukrainian President Volodymyr Zelenskyy was a “puppet” placed on his throne by Washington and his unpopular government is incapable of standing up to the great Tsar Vladimir;” “Ukraine’s western provided weapons are no match for Russia’s incredible arsenal;” “Ukraine’s Armed Forces cannot stand up to the Russian Military, which is the best in the world;” “The North Atlantic Treaty Organization (NATO) was a weak organization that would collapse under the weight of Moscow’s greatness and would never stand up to Putin over Ukraine”. I could go on.
Instead of being met with ‘Bread and Salt’ in the winter of 2022, Russian forces were greeted with Javelins, Stingers, and Bayraktar Unmanned Aerial Vehicles (UAV) and highly motivated Ukrainian forces that humiliated the Russians on the battlefield and stopped Moscow from achieving its initial objectives. More than three years later, the Russian people have suffered over a million Russian casualties and now face serious social and economic problems.
When President Trump returned to the White House in January 2025, it appeared Putin’s echo chamber once again failed the Russian President, who was apparently convinced that he could deceive and manipulate Trump endlessly by pretending to want to find a diplomatic solution to the crisis in Ukraine, while continuing to launch attacks on Ukraine day and night.
For months, President Trump and his Administration tried to look past Putin’s deceitful behavior. The U.S. president appeared willing to “turn the other cheek” when Putin blatantly insulted him by launching strikes while Trump’s Special Envoy was in Moscow to “talk peace” and Trump’s emissaries were in Kyiv to encourage the Ukrainians to consider making compromises to end the war. Fueled by his own arrogance and lacking advisors around him who will speak the truth, Putin repeatedly insulted the U.S. president and the people who elected him to lead the United States.
The Cipher Brief Threat Conference is happening October 19-22 in Sea Island, GA. The world's leading minds on national security from both the public and private sectors will be there. Will you? Apply for a seat at the table today.
If the Russians really understood what they were dealing with in President Trump, Putin would have known that there was a limit to what he could get away with vis-a-vis his American counterpart. Instead, his complete failure to understand the dynamics in the U.S. and Trump’s own personality has finally led to the U.S. president turning a corner — recently announcing his support for continued military support to the Ukrainians in their fight to defend their country against Putin’s aggression, and his willingness to seriously consider adopting secondary sanctions that will place increased pressure on the already struggling Russian economy.
Trump is calling Putin’s bluff, and the Russian people will once again pay the price for their “leader’s” lack of judgement and self-awareness.
For those Americans who support continued U.S. assistance to Ukraine and recognize that the loss of Ukraine to Putin will have dire consequences for the U.S. far beyond the battlefield, the U.S. president’s recent shift in thinking is a very welcome sign that the White House understands that in any confrontation with Putin, the U.S. can and will demonstrate the fortitude and stamina needed to counter the Russian dictator’s imperial ambitions and that Washington will not tolerate being insulted by Putin.
Continued supplies of defense weapons, the removal of Biden-era restrictions on how the Ukrainians can use U.S. weapons systems, and increased economic pressure on the Russian regime are all important steps that the U.S. can now take to demonstrate to Putin that he is wrong if he thinks he can bully the American people and their elected leaders.
But there is another tool that President Trump can also use to increase pressure on Putin – his own voice.
During the 2016 U.S. Presidential elections, then-candidate Trump openly spoke about his desire to forge better relations with Russia. After his election, he continued to try to improve relations with Moscow despite facing significant attacks from his political opponents in Washington. As a result, during Trump’s first term in office he was very popular among the Russian people, who were hopeful that their government would take advantage of Trump’s positive feelings about their country and take advantage of the opening Trump was offering to improve their lives.
After being re-elected to the White House in 2024, the Russians were once again offered an opportunity to reduce tensions with the U.S. and roll-back economic sanctions and the diplomatic isolation that have undermined the hopes many Russians had in the past of living a better life. Between January and June 2025, Trump offered Putin multiple openings to find an off-ramp to the costly war in Ukraine. Putin not only failed to take advantage of the opportunities presented by Trump, but he openly thumbed his nose at the U.S. president.
Everyone needs a good nightcap. Ours happens to come in the form of a M-F newsletter that keeps you up to speed on national security. Sign up today.
In the 1980’s, Republican President Ronald Reagan understood the importance of communicating directly to the people of the Soviet Union. His message then was clear – The United States is not your enemy. Your enemy is the corrupt regime that denies you basic liberties and has dragged you into an expensive arms race with the United States that is robbing you of your ability to enjoy a better life.
During that era, Reagan used every possible means to communicate his message to the Soviet people and by the early 1990s, his strategic messaging campaign worked, when the people of the Soviet Union rose up against their jailers and demanded an end to the Communist Party’s control over their lives.
President Trump should follow Reagan’s example and look for every opportunity to communicate to the Russian people that it is Putin, not Trump, who refuses to engage in negotiations aimed at improving their lives. It is Putin, driven by his selfish arrogance and detachment from reality, who is squandering Russia’s future.
Washington is ready to work with Russia – but only when Russia ends its attacks on its neighbors and demonstrates a sincere willingness to settle its differences with those neighbors via peaceful means, versus costly military conflicts that result in the senseless death and suffering of the average Russian, who under current circumstances will never see any benefit from Putin’s war.
The Cipher Brief is committed to publishing a range of perspectives on national security issues submitted by deeply experienced national security professionals.
Opinions expressed are those of the author and do not represent the views or opinions of The Cipher Brief.
Have a perspective to share based on your experience in the national security field? Send it to Editor@thecipherbrief.com for publication consideration.
Read more expert-driven national security insights, perspective and analysis in The Cipher Brief