Two of America’s greatest failings, certainly regarding post-World War II foreign policy, have been profound shortcomings in knowledge and understanding of events and circumstances in which the US has engaged, particularly with force. The great Chinese philosopher of war, Sun Tzu, rightly observed that knowing the enemy was vital to success. From Vietnam to Afghanistan and later Iraq, that was not the case. And these are only a few examples. Despite the adulation given to President John F. Kennedy over successfully ending the Cuban Missile Crisis in October 1964 forcing the Soviet Union to remove its nuclear missiles from that island ninety miles off the Florida Coast, the consequence was to provoke an arms race probably extending the Cold War. Soviet leader Nikita Khrushchev had sought to reduce defence spending and divert those rubles to the civilian sector. After the crisis, he was forced to ramp up defence spending. Kennedy entered office in January 1961 promising to strengthen American defences and reverse the “huge missile gap” allegedly in Moscow’s favour. In fact, America then possessed overwhelming nuclear superiority and the missile gap was Russia’s. That failure of knowledge and understanding would persist. Four years later, no second North Vietnamese PT boat attack against two US Navy destroyers took place to provoke the Tonkin Gulf Resolution and American entry into that war. Forty-two years later, there were no Iraqi weapons of mass destruction. The question today is whether the US is repeating its lack of knowledge and understanding of Russia and its President Vladimir Putin. The great Chinese philosopher of war, Sun Tzu, rightly observed that knowing the enemy was vital to success. An earlier column explained how and why Putin’s thinking evolved to where he saw the US as untrustworthy and dangerous. It explained the factors leading to Russia’s unprovoked invasion of Ukraine. Now, is Putin really uninformed about the state of the war in Ukraine and why he believes he is prevailing? First, leaders find admitting fault distasteful. In part that demonstrates why the US remained so long in Vietnam, and Afghanistan for twenty years and still has forces in Iraq. Donald Trump’s refusal to accept losing the 2020 election is another stunning example of that failure to recognize the fact. Then how might Putin be analyzing events and what are his broader strategy and goals? One of the reasons America has too often failed in seeking knowledge and understanding is more than mirror imaging. It is hubris to believe that most sensible people think and behave as we do or should. This sometimes messianic aim of exporting democracy and values does not always work. President Joe Biden’s recent trip to Saudi Arabia captures this contradiction and lays it bare. As Henry Kissinger who has met with Putin at least fifteen times observed, the Russian president is very “analytical.” From that perspective and measured by the UN Resolution condemning Russia’s aggression, states representing a majority of the global population either voted no or abstained, China, Brazil, India and South Africa among them. Thus, Putin is playing to a larger audience to counterbalance the US, Europe and the West who are the “enemies,” opposed to Russian interests and containing its ambitions, prosperity and autonomy. Hence, the energy deals with China will keep the coffers filled. Putin’s meeting in Iran with its President Ebrahim Raisi and Turkey’s President Recep Tayyip Erdogan is a further means to outflank and divide the West by cultivating both leaders. And joining OPEC and seeking a closer relationship with Saudi Arabia, in essence, to replace the US is a smart ploy by Putin. In Ukraine, Putin believes he can win much as other leaders have persisted in that belief. Here, size is on his side. While Ukrainian forces have fought with courage, brains and skill, while the Russians have not certainly in terms of competence, at some stage, all the “dumb Russians” will be dead and a few good generals will ultimately become replacements. The questions are whether Ukraine can replace its losses in ground forces and equipment and if Western support will flow in sufficient quantities and quality of weaponry to keep pace with Russian numerical superiority. One conclusion is that the US needs a global strategy to deal with Russia and for that matter China. The new, soon-to-be-released National Security Strategy is likely to be a continuation of past ones with the aims of containing, deterring and if war comes defeating a range of potential adversaries topped by China and Russia. But containing and deterring have not worked. Does anyone understand that? The writer is a senior advisor at Washington, DC’s Atlantic Council and a published author.