Vladimir Putin knows better than to expect too much of Donald Trump, who shocked the world by winning the U.S. presidential election last night. He’s been disappointed by new U.S. Presidents before. Two of them have taken office during Vladimir Putin’s years in power, both with grand plans to mend ties with Russia—and both plans collapsed amid what Russians tend to see as the intrinsic rivalry between the two powers. So the Russian President was careful not to get his country’s hopes up for a quick rapprochement with the U.S. on Wednesday.

“We realize and understand that this will not be an easy road given the level to which our relations have degraded,” Putin said in congratulating Trump on his electoral victory. A moment later, he added, “We know this will not be easy.”

After a campaign that saw Trump repeatedly praise Putin’s leadership and promise to mend relations, the U.S. President-elect would likely need to grant Russia a string of concessions in order to fulfill that promise. To start with, he would need to lift the sanctions the U.S. imposed in response to Russia’s military aggression against Ukraine in 2014. He may also need to pull back the troops that NATO deployed near Russia’s border in response to that conflict, and perhaps most important of all, he would need to scrap or at least scale back the missile defense shield that the U.S. had intended to build over Europe, a project that Russia has seen as a direct threat to its security.

Read More: Hacked Kremlin Emails Could Signal a Turn in the U.S.-Russia Cyberwar

All of these concessions would likely infuriate U.S. allies and erode U.S. influence, particularly in Eastern Europe, where the newer members of the NATO alliance have felt the most vulnerable to Russian attacks. But Trump and his advisers have seemed perfectly comfortable with that trade-off during the campaign. In interviews and speeches, he has suggested that NATO is obsolete, and that its members should start paying for their own defense instead of relying on the U.S. security umbrella.

“Up until now these eastern European states felt America’s protection,” Alexander Rahr, a Russian expert on foreign affairs, wrote in an analysis of the election results. But under a Trump presidency, he added, “the Poles and the Baltic states will have to put their tails between their legs and adjust to the new situation.”

Rahr was not the only one in Moscow to let his imagination run wild on Wednesday. The Russian senator Olga Kovitidi said that, under Trump, the U.S. would be certain to recognize the Russian annexation of Ukraine’s Crimea region—a move that led to U.S.-led sanctions against Russia—as legitimate. Sergei Glazev, a senior Kremlin adviser, said that Trump, “as a pragmatic person,” would be sure to lift those sanctions.

Read More: Economists Warn of Global Recession Following Trump Victory

But with all these changes in the air, why was Putin so careful to stress how hard the road to rapprochement would be? It’s possible that he was simply playing hard to get as he prepares to negotiate with Trump over exactly how much the U.S. will yield to Russia’s wishes. Or it could just be the caution that comes with experience.

Back in 2001, the second year of Putin’s presidency, George W. Bush entered the White House with a pledge to improve ties with Russia, famously telling reporters that he had looked into Putin’s eyes and gotten “a sense of his soul.” But within a few years, the relationship was back on the rocks, largely because of the Bush Administration’s support for pro-democracy movements in the former Soviet world and the westward political drift of the countries in Russia’s neighborhood. “It all confirmed Putin’s eternal suspicions of the Americans as inveterate hypocrites,” Mikhail Zygar, a Russian journalist, wrote of that period in his recent book, All the Kremlin’s Men.

The next U.S. President solidified that suspicion. Much like Bush, President Barack Obama placed the improvement of ties with Russia at the center of his foreign policy agenda during his first months in office. But Putin realized that Obama’s so-called “reset” policy toward Russia would not resolve the key points of contention between the two countries: NATO’s eastward expansion continued under Obama, as did the U.S. plan to build a missile shield over Europe. The American habit of talking down to Russia over human rights also persisted, confirming Putin’s impression that “America does not need allies, it needs vassals,” as he put it in 2011.

Read More: Trump’s Victory Injects Uncertainty into a Chaotic Middle East

With that experience in mind, Russia’s foreign policy establishment tends to be guarded in its expectations for incoming U.S. Presidents. “On the whole, we work on the assumption that our countries are systematically opposed to each other, and that will hold regardless of who’s the head of state,” Fyodor Lukyanov, a leading Russian expert on foreign affairs, told me during the campaign.

But he acknowledged that Trump is different. No U.S. President in recent history has expressed such a clear desire to turn inward and roll back American military and political commitments around the world. “Trump is the American hangover after a quarter-century binge on power,” says Lukyanov. And as American power recedes, Russia has shown its willingness to advance and fill the vacuums, particularly in Syria, whose civil war has at times looked like a proxy conflict between the U.S. and Russia over the past year.

Untangling that mess will represent an enormous challenge for the Trump Administration, and he does not seem likely to bother too much with problems of foreign affairs over the next few months, says Alexander Konovalov, an expert on U.S.-Russian relations in Moscow. “The problem surrounding Ukraine and Syria will remain,” he says. “No one has yet suggested any serious path out of either crisis.”

And as Putin was careful to stress on Wednesday, that path will be difficult. “It is not Russia’s fault that our relations with the United States have reached this point,” he said. So in his thinking, it is not Russia that needs to start granting favors in order to fix those relations. It will be Trump’s job to make an offer, and Russia’s prerogative to ask for more.

Get The Brief. Sign up to receive the top stories you need to know right now. Please enter a valid email address. Sign Up Now Check the box if you do not wish to receive promotional offers via email from TIME. You can unsubscribe at any time. By signing up you are agreeing to our Terms of Use and Privacy Policy . This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply. Thank you! For your security, we've sent a confirmation email to the address you entered. Click the link to confirm your subscription and begin receiving our newsletters. If you don't get the confirmation within 10 minutes, please check your spam folder.

Contact us at letters@time.com.