As President Obama scrambles for some kind of a response to Russia’s moves in Ukraine, the stakes for the President and his foreign policy could not be bigger. Putin’s Crimean adventure isn’t just a blow to American plans for Ukraine; it shakes the foundations of the President’s world strategy and in a worst-case scenario could fatally weaken President Obama at home.

Behind the scenes, we are told, the White House spin machine is telling friendly reporters (of which there are many, though perhaps not so many as in 2009) that, in essence, Vladimir Putin has fallen into a trap. “I’ve got him where I want him,” as the hunter said when the bear chased him up a tree.

There is a sense in which this is actually true; Putin is leading Russia down a dead end and the creation of a corrupt, authoritarian and brutal state resting on the exploitation of hydrocarbons will over time weaken and marginalize Russia in world affairs. As a further step down that dark road, the Ukrainian invasion deepens the historical crisis of modern Russia and makes positive progress both more difficult and less likely. There are two kinds of state-building autocrats. Some throttle freedom and succeed in building a strong and modernizing state; names like Kemal Ataturk, Augusto Pinochet and Lee Kwan Yew come to mind. Others throttle freedom and have nothing to show for it—people like Juan Peron, Benito Mussolini, and Slobodan Milosevic. Putin is increasingly likely to go down in history as a failed state builder, a man who took Russia down the wrong path and who added to the burden of Russian history.

But those are long term considerations that, unfortunately for the diligent White House staffers working to spin the next news cycle, won’t help the President now.  In the short term President Putin has put President Obama in an ugly spot. President Obama’s foreign policy depends on three big ideas: that a working relationship with Russia can help the United States stabilize the Middle East, that a number of American adversaries are willing to settle their differences with us on the basis of compromises that we can accept, and that President Obama has the smarts to know who we can trust.

Putin’s attack on Ukraine calls all three propositions into question. What Obama’s belief in the possibility of deals with countries like Russia and Iran leaves out is that some countries around the world may count the reduction of American power and prestige among their vital interests. They may not be hampering and thwarting us because we are unnecessarily and arbitrarily blocking their path toward a reasonable goal; they may be hampering and frustrating us because curbing our power is one of their central objectives. This is not necessarily irrational behavior from their point of view; American power is not a good thing if you hate the post-Cold War status quo, and it can make sense to sacrifice the advantages of a particular compromise with the United States if as a result you can reduce America’s ability to interfere with your broader goals.

If that is true, our adversaries might still reach and even keep certain agreements with us, but they would be constantly looking to damage us. Russia’s goals in Syria, for example, might well include the ‘rational’ goals that President Obama thinks could form the basis of a compromise agreement—the defeat of Sunni jihadism, protection of Russian civilians and economic interests in the country and so on—but could also include the goal of using the Syrian war as a method of scoring both propaganda and realpolitik victories against the United States. America is more important to Russia than Syria is; Putin could rationally believe that his interest in weakening America was more important than some of his other interests in Syria. Lucy doesn’t have to be motivated by Iago-like irrational malice when she pulls the football away from Charlie Brown; there can be valid reasons why she wants Charlie Brown flat on his back.

Iran, too, may have rational interests that Obama hasn’t fully taken on board. One of Iran’s objectives in entering talks with the United States over the nuclear issue at a time when the Shiite theocracy appears to be tightening its hold across the Fertile Crescent might be to drive a wedge between the United States and its Sunni allies.

Washington’s flat-footed, deer-in-the-headlights incomprehension about Russia’s Crimean adventure undermines President Obama’s broader credibility in a deeply damaging way. If he could be this blind and misguided about Vladimir Putin, how smart is he about the Ayatollah Khamenei, a much more difficult figure to read? President Obama is about to have a difficult meeting with Prime Minister Netanyahu in which he will tell Netanyahu essentially that Israel should ground its national security policy on the wisdom of President Obama and his profound grasp of the forces of history. The effect will be somewhat undermined by President Obama’s failure to understand the most elementary things about Vladimir Putin.

With Hitler-style lies blasting from the well-tuned Russia propaganda machine (attacks on ethnic Russians! mass flight of refugees! fascism!) and armed soldiers backing up thugs in Crimea and elsewhere, President Putin is not exactly looking like a partner for peace at the moment—and Obama’s decision to work with him isn’t making President Obama look like a foreign policy genius.

Prime Minister Netanyahu—and many other world leaders—will be looking at President Obama with cold and calculating eyes. They can see that he turned to Russia for help when his Syrian red line policy collapsed; they can see that he is betting heavily that Russia will help him with Iran, both in the negotiations and at the UN Security Council.  They observe how Washington was flabbergasted and stunned by the events in Ukraine, and they are likely to conclude that President Obama’s Middle East policy is in much worse shape than he thinks.

Both friends and foes are also probably thinking today that President Obama is going to have less control over the future of American foreign policy than he might like. The Republicans seem increasingly poised to capture the Senate in 2014 and unless Elizabeth Warren sprints past Hillary Clinton in the Democratic race for 2016, the next US President, whether Democrat or Republican, will likely take a tougher line on international issues than President Obama does. Obama might hope that this will make other countries more willing to sign agreements with him because he might offer them a better deal than they could hope from his successor, but they are just as likely to draw the opposite conclusion. Deals with Obama, they may think, won’t stick because his successors won’t want to honor them.

Ukraine is a particularly tough problem for President Obama because it points to one of the weak spots in the Wilsonian-Jeffersonian foreign policy synthesis he seeks to build. As a Wilsonian, Obama wants to change the world. He wants international relations to be built on the foundation of international law. He wants nuclear weapons first controlled, then reduced and finally abolished. He wants human rights to be observed around the world. But as a Jeffersonian, he believes, deeply, that excessive American commitments and activism beyond our frontiers endanger both the peace of the world and our freedoms at home. He wants to cut back, he wants to avoid war, and he wants America to meddle less and pay less.

He wants, in other words, to pay less into the international system, and take more out.

There is nothing wrong with this as a goal. It is a perfectly rational thing to desire. But the pursuit of it can lead to some strange places, and President Obama is in one of them today.

Here’s the rub. When Ukraine escaped from the Soviet Union in 1990, Soviet nukes from the Cold War were still stationed on Ukrainian territory. After a lot of negotiation, Ukraine agreed to return those nuclear weapons to Russia in exchange for what (perhaps naively) its leaders at the time thought would be solid security guarantees from the United States and the United Kingdom. The “Budapest Memorandum” as this agreement is called, does not in fact require the United States to do very much. We can leave Ukraine twisting in the wind without breaking our limited formal obligations under the pact.

If President Obama does this, however, and Ukraine ends up losing chunks of territory to Russia, it is pretty much the end of a rational case for non-proliferation in many countries around the world. If Ukraine still had its nukes, it would probably still have Crimea. It gave up its nukes, got worthless paper guarantees, and also got an invasion from a more powerful and nuclear neighbor.

The choice here could not be more stark. Keep your nukes and keep your land. Give up your nukes and get raped. This will be the second time that Obama administration policy has taught the rest of the world that nuclear weapons are important things to have. The Great Loon of Libya gave up his nuclear program and the west, as other leaders see it, came in and wasted him.

It is almost unimaginable after these two powerful demonstrations of the importance of nuclear weapons that a country like Iran will give up its nuclear ambitions. Its heavily armed, Shiite-persecuting neighbor Pakistan has a hefty nuclear arsenal and Pakistan’s links with Iran’s nemesis and arch-rival Saudi Arabia grow closer with every passing day. What piece of paper could Obama possibly sign—especially given that his successor is almost certainly going to be more hawkish—that would replace the security that Iran can derive from nuclear weapons? North Korea would be foolish not to make the same calculation, and a number of other countries will study Ukraine’s fate and draw the obvious conclusions.

President Obama is an articulate, thoughtful man. Anybody who doubts it should read his interview with Jeffrey Goldberg at Bloomberg News, where the President of the United States offers up an intellectually serious, robust and closely reasoned defense of his overall foreign policy. But it’s not clear that his worldview meshes well with the way the world actually works.

While the outcome of crises like this one are impossible to predict and the President could still conceivably turn things around, President Obama’s personal prestige and political authority are balanced on a knife edge. Like JFK after the Bay of Pigs, like Lyndon Johnson after the Tet offensive, like Harry Truman after North Korea attacked the South, like Dwight Eisenhower when the Soviets rolled into Hungary and Ike stood helplessly by, like Ronald Reagan when Iran-Contra blew up in his face, at the moment President Obama has what appears to be a big, fat, ugly, icky and stinky foreign policy fiasco on his hands.

Now as this list shows, foreign policy flops aren’t all that rare; every American president since FDR has had at least one big one. Foreign policy is much, much harder than it looks and only the luckiest of presidents can hope to make it to the finish line without an embarrassing fiasco or two. President Obama is in good company today, and almost every American president must sooner or later learn to cope with these meltdowns. It goes with the job.

Foreign policy flops don’t have to be politically fatal. Jimmy Carter, Harry Truman and Lyndon Johnson all either lost re-election bids or dropped out to avoid humiliating losses after big overseas setbacks, but George W. Bush was re-elected long after Iraq had turned sour, nothing could derail Dwight Eisenhower and President Kennedy’s re-election looked to be building momentum at the time of his death.

In looking back at the record of presidential foreign policy misfires, they seem to divide into two categories. Some, as when the Soviets shot down an American U-2 spy plane in Soviet airspace and used the incident to embarrass President Eisenhower, don’t have a lot of impact. These are seen as errors in execution of a policy that is fundamentally sound. As long as there aren’t too many of them and they aren’t too costly, presidents usually manage these reasonably well.

It is the failures that raise basic questions about a president’s ability to do the job, or that appear to demonstrate that his policies are fatally flawed that hurt most. Jimmy Carter’s failure to rescue the hostages cemented the public impression that he was out of his depth and helped open the door to Ronald Reagan. The shock of the Tet offensive, despite ending with a military defeat of the North Vietnamese, convinced a critical mass of the public that Lyndon Johnson’s entire Vietnam strategy was flawed. By 2005/6, the failure to pacify Iraq following the failure to find WMD in the country fatally weakened George W. Bush’s authority and popularity.

This is President Obama’s chief political risk as the Ukraine crisis continues. If the American public comes to see this as just another case of horrible foreigners doing horrible things in a faraway place, Russia’s Crimean romp will only have a limited effect on the President’s authority and popularity. But if the public sees the Russian rampage as decisive evidence that President Obama is too naive, too passive and too, well, Carteresque, then his presidency could be holed below the waterline, and he could lose much of his ability to shape perceptions and policy on a range of other issues at home and abroad.

The specter of Jimmy Carter, temporarily but not permanently banished by the successful raid on Bin Laden, is what has haunted this president’s foreign policy from the beginning. President Obama’s mix of Wilsonian aspirations and Jeffersonian caution is closer to Jimmy Carter’s basic worldview than to that of any other modern president. So far, President Obama and his team have managed to fend off the specter of Carterization, mostly by managing events more successfully than the Carter team could do, but also because American power in the world today is much greater than it was in the Carter years and we enjoy a larger margin of error.

The Obama administration is now being challenged, and not only in Crimea. Both friends and foes around the world (and in the United States) increasingly see a Georgia peanut farmer when they look towards the Oval Office. If President Obama allows that impression to become irremovably fixed, he and the nation he leads have some ugly times ahead.

The question, of course, is what do you do next? I will be back later this week with some thoughts on this difficult subject. Meanwhile, keep your eyes on Ukraine. As I wrote in an essay last year, the events in Ukraine show us world history being made. Unfortunately, world history isn’t always very nice.