Trump’s Playbook: How Putin outsmarted 4 US presidents, then was outplayed by 'The Donald'

Now that Donald Trump has secured a historic victory, returning to the White House for another term in January, assorted pundits are pontificating that the president-elect will give away the store to Russia’s president, Vladimir Putin, especially when it comes to resolving the almost three-year Russia-Ukraine conflict.

I’m here to tell you that President-elect Trump is a gift to Ukraine and a nightmare for Putin. 

Trump is the first U.S. president who has been able to outsmart the Russian dictator after the latter had fooled four U.S. presidents. Yes, Bill Clinton, George W. Bush, Barack Obama and, of course, President Biden. All fell for the "former" KGB operative’s chicanery, having gullibly trusted Putin that Russia could be America’s friend.

George W. Bush famously proclaimed that he "looked the man [Putin] in the eye." Bush described Putin, the "former" KGB operative, as "consistent, transparent, honest, and an easy man to discuss our opportunities and problems with," according to the White House archives.

Friendship? Common values? Seriously? The FBI had just arrested its own agent, Robert Hanssen, a 20-year spy for the KGB, in February 2001. The most damaging spy in modern history, Hanssen sold some of the most sensitive U.S. secrets to the Russians, including our nuclear secrets, the existence of a secret American-built tunnel under the Soviet Embassy in Washington, D.C., and the identities of Soviets who spied for America.

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President Trump and Russian President Vladimir Putin are shown at the APEC summit in Danang, Vietnam, on Nov. 11, 2017. (Reuters/Jorge Silva)

Evidently, Bush and his advisers weren’t deterred by the fact that Putin’s first Foreign Policy Concept pronounced America’s "economic and power dominance" as a threat to Russia’s national interests and his first military doctrine alluded to the North Atlantic Treaty Organization (NATO) being a top threat to Russia’s security. Both were approved by Putin in 2000.

Even the terrifying revelation made by the House Armed Services Committee in October 1999 about Russia’s "sabotage plans" against the United States failed to prevent the spell that Putin projected on Bush. Transcripts of congressional testimonies reveal that the committee had in its possession "dramatic evidence" of the KGB's positioning on NATO territory and possibly United States territory caches of high explosives and arms intended for sabotage operations in the event of war.

Bush wasn’t the first U.S. president played by Putin. Vlad began his charm offensive targeting U.S. presidents for manipulation with Bill Clinton. Clinton called Putin on Mar 27, 2000, the day after the Russian elections, to congratulate him on his victory. Declassified White House records reveal a very chummy phone call in which the leaders of former Cold War archenemies called each other by their first names, Vladimir and Bill.

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Presidents Obama, George W. Bush and Clinton are shown during the first round of the Presidents Cup at Liberty National Golf Club in Jersey City, N.J., on Sept. 28, 2017. (Shelley Lipton/Icon Sportswire via Getty Images)

Clinton expressed eagerness to build relations with his Russian counterpart and "the relationship between the U.S. and Russia."

"We can accomplish a lot together," he told Putin. And Vladimir responded in kind, assuring Bill that his trust wasn’t misplaced.

"It is clear to the whole world that I am a person you can work with," Putin said, and he thanked Clinton for his comments about the Russian dictator’s "modest personality."

"The statement that you made about my modest personality was not unacknowledged here … this statement by the U.S. president was not unnoticed by people in Russia and throughout the world." 

Declassified transcripts of 500 pages of telephone conversations between Britain’s Tony Blair and former President Clinton that occurred between 1997 and December 2000 reveal that "Slick Willie" was also under Vlad’s spell. Clinton considered Putin "smart and thoughtful," someone with "enormous potential."

"I think [Putin] is a guy with a lot of ability and ambitions for the Russians. His intentions are generally very honorable and straightforward, but he just hasn’t made up his mind yet," Clinton told Blair.

Barack Obama was next. He famously promised Putin’s proxy, then-President Dmitry Medvedev, "more flexibility" in American policy toward Russia, unaware that his conversation was captured by a microphone. In 2013, Putin dissuaded Obama from following through on his earlier warning that Syria’s president, Bashar al-Assad, crossed the "red line" when he targeted his own citizens with a chemical strike. Another of Putin’s proxies, Russian Foreign Minister Sergey Lavrov, convinced his counterpart, John Kerry, that there was no need for a punishing strike because Russia would remove the chemical weapons arsenal from Syria. Putin’s maneuver allowed Obama to save face while claiming a diplomatic victory.

The identification and business card of former FBI agent Robert Hanssen are seen inside a display case at the FBI Academy in Quantico, Va. (PAUL J. RICHARDS/AFP via Getty Images)

Four years later, however, Assad was still gassing his people. That is until on April 7, 2017, when President Trump enforced Obama’s 2012 "red line." Authorized by Trump, the U.S. military launched 59 Tomahawk cruise missiles at the Shayrat Airbase in Homs, the source of a sarin gas attack that killed more than 80 Syrians on April 4, 2017.

When he characterized his relationship with Obama as "working and personal" marked by "growing trust," what Putin really meant was that he had outsmarted yet another U.S. leader and that his KGB tactics were working well, for Russia that is. After all, it was on Obama’s watch that Russia invaded Crimea and made it part of Russia in 2014. And it was on Biden’s watch that Putin invaded Ukraine in 2022 after Biden green-lighted this action with his "minor incursion" comment.

Putin managed to trick four presidents to begin their terms with the pursuit of a naive Russia "reset" policy doomed to failure from the very start.

North Korean leader Kim Jong Un, right, and Russian President Vladimir Putin

How does the Russian master manipulator do it?

Putin prides himself on his ability to "work and communicate with people" and to "work with information." Working with information means learning everything about your target. Working with people means communicating with your target in a way that appeals to his vanity. Pushing your target’s buttons and exploiting his vulnerabilities is classic intelligence tradecraft. Putin honed these skills as a KGB operative, recruiting spies in Eastern Germany who were willing to betray their country in service to Russia.

When his close friend asked him what his job as a KGB officer entailed, Putin responded that he was a "specialist in communicating with people," which can also be translated as "a specialist in human relations." During a press conference in 2001, Putin explained that working with people entails the ability to communicate with a wide range of individuals, from journalists and scientists to politicians and rank-and-file citizens: "It is important to establish a dialogue and activate the best in your partner. You want to achieve results; you must respect your partner, acknowledge that he is better than you in some way. You must make him your ally … make him feel that there is something that unites you, that you have a common cause."

Even the American media was so beguiled by the KGB operative in the Kremlin that Putin was chosen as "Person of the Year" by Time magazine in 2007 and four times in a row from 2013 to 2016 by Forbes magazine as the "World’s Most Powerful Individual."

President Joe Biden meets with President-elect Donald Trump in the Oval Office of the White House, Wednesday, Nov. 13, 2024, in Washington. (AP Photo/Evan Vucci) (AP Photo/Evan Vucc)

Putin’s trickery didn’t work with former President Trump, however. 

You see, Trump invented the game. He loves talking with people and understands the value of communicating, even with foreign dictators. Last month, Trump angered the commentariat when he told Bloomberg editor-in-chief John Micklethwait that talking with Putin is a "smart thing."

Replying to Micklethwait’s question about whether he had continued contact with Putin after leaving the White House in 2021, Trump said, "But I will tell you that, if I did it, it’s a smart thing. If I’m friendly with people, if I have a relationship with people, that’s a good thing, not a bad thing."

A talented businessman with an authentic communication style and natural ability to connect with people, Trump is well-positioned to outfox Putin. Out-negotiating and outsmarting his counterpart comes with the territory for a successful entrepreneur. To negotiate a better deal, you have to be super attuned to your interlocutor’s personality, allowing you to accurately assess his strengths and weaknesses. Trump has this innate ability to size up people and learn quickly what makes them tick. Even former Democrat lawmaker Claire McCaskill admitted on Wednesday that President-elect Trump knows our country "better than we do."

Republican presidential nominee Donald Trump arrives to speak at an election night event in West Palm Beach, Fla., on Nov. 6, 2024. (Chip Somodevilla/Getty Images)

This talent has served Trump well in dealing with Putin. Realizing that the Russian strongman responds well to respect, Trump doesn’t disparage Putin, unlike Biden, Harris and other Western politicians. And what is the point? Putin is not afraid of words. He is afraid of actions. So, Trump gave the Russian spymaster action.

Having understood Putin’s anti-U.S. strategy, Trump has taken several specific steps to counter Russia’s war-fighting doctrine and weaken its combat potential. Realizing that energy is the main source of Russia’s defense economics fueling Putin’s war machine, Trump sanctioned the Nord Stream 2 pipeline in December 2019, angering Putin.

The same month, Trump founded America's first entirely new armed service since 1947, the U.S. Space Force. This action sought to mitigate Russia’s space warfare doctrine. This doctrine called for Russia’s space troops, which Putin stood up in 2001, to attack U.S. satellites on which we depend for every aspect of war-fighting and in our civilian life.

In 2018, as part of the modernization of the U.S. nuclear arsenal, Trump ordered the development of a low-yield, nuclear-armed, sea-launched cruise missile. This was a direct counter to Putin’s "escalate-to-de-escalate" atomic strategy, which seeks to detonate a low-yield tactical nuclear warhead in the theater of combat operations, such as in Ukraine, to deter the U.S. from intervening. 

Foolishly, the Biden-Harris administration canceled Trump’s program. Biden’s cancellation of the Keystone XL pipeline in 2021 helped fuel Putin’s war machine by boosting Russia’s oil revenues as energy supply fell after the U.S. oil production capacity dropped by more than 800,000 barrels. In fact, the United States was importing nearly 600,000 barrels of oil a day from Russia, a gap that Keystone could have made up for.

There’s a reason why Putin didn’t invade anyone on Trump’s watch and is now terrified of the next Trump presidency. Vlad knows that "Teflon Don" is onto him and can beat him at his own game.

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Rebekah Koffler is a strategic military intelligence analyst and a freelance editorial writer. She is the author of Putin’s Playbook; Regnery 2021, and the host of a podcast "Censored But Not Silenced." Rebekah also is the Author of American Bolsheviks: The Persecution of Donald Trump and the Sovietization of America; Post Hill Press, November 12, 2024. Twitter: @rebekah0132