Derek Chollet is executive vice president of the German Marshall Fund and author of "The Long Game: How Obama Defied Washington and Redefined America’s Role in the World." He will be presenting at the Miller Center's conference on Russia and the U.S. presidency, Nov. 8-10, 2017.

Was Barack Obama too soft on Vladimir Putin? (Justin Lane/European Pressphoto Association)

In the spring of 2012, soon after Vladimir Putin returned to the Russian presidency, President Barack Obama convened a meeting in the White House Situation Room to discuss the way forward. Obama had invested a lot in the “reset” with Russia, and he believed it had achieved some meaningful wins. But having first met the Russian leader during a tense 2009 meeting in Moscow, where he was subjected to one of Putin’s customary harangues about the West’s betrayals, Obama understood that U.S.-Russia relations were likely to get worse.

“The main challenge is to put him in a box to stop making mischief,” Obama said of Putin. Yet he wondered what leverage the United States had to influence the Russian leader, and he struggled with how to send this message in a way Putin would understand. “We have to look him in the eye,” Obama said — referring to President George W. Bush’s infamous statement in 2001 that he had looked into Putin’s eye and gotten a sense of his soul — “to tell him, ‘Don’t think you can screw around without consequence.’”

But when Obama left office four years later, Putin was anything but boxed in. Indeed, many saw Russia as resurgent: threatening European stability, gaining the upper hand in key regions such as the Middle East and, perhaps most worrying, directly (and effectively) interfering in the 2016 U.S. presidential election.

Given this outcome, Obama’s approach toward Moscow is one of the most controversial aspects of his foreign policy legacy. Did wishful thinking produce a failed policy, perhaps best symbolized by Obama’s glib dismissal of Mitt Romney’s tough talk on Russia during the 2012 presidential campaign? Or was it a reflection of the inherent limits of U.S.-Russia relations under Putin? The answer is a mix of both, which offers important lessons for the future that can be summed up this way: Don’t oversell, don’t chase, and take time to understand how Russia’s decline limits cooperation.

Since the end of the Cold War, partisan disputes on how to approach Russia have largely been over how most effectively to influence Russian behavior, especially when it turns negative. Should the United States seek to engage or isolate Russia? Accommodate the Kremlin or confront it? These debates served a shared underlying goal: to help promote a democratic Russia at peace with itself and with its neighbors, one that could cooperate with the rest of the world in solving regional and global problems.

Obama entered office hoping to work with Moscow on common endeavors, such as nuclear security, trade and investment, and regional worries like Iran and North Korea. He harbored deep concerns about Russia’s political direction and Moscow’s dealings with its neighbors and had been critical of the Kremlin during the 2008 U.S. presidential campaign. But he understood that improved relations with Russia could and should be a means to achieving American security and economic objectives.

That was the core logic behind the so-called reset. It was not some ill-conceived attempt to work with Russia at all costs, brush aside differences or establish an enduring new era of harmony. Instead it reflected the practices that have governed the U.S.-Russia relationship since the end of the Cold War: a mix of cooperation, competition and disagreement. The reset was driven by pragmatism, not ideology; it was an effort to work with Russia where interests converged, stand firm where they did not and engage directly with the Russian people as they pressed for political freedom and economic reforms.

During Obama’s first term in office, when Dmitry Medvedev was Russia’s president and Putin remained lurking behind the scenes as prime minister, the reset paid dividends on several priority issues — reducing nuclear weapons through the New START treaty, imposing the toughest-ever U.N. sanctions on Iran and opening a key supply line for U.S. forces in Afghanistan. The two countries also increased trade and foreign direct investment and worked together to allow the United Nations to authorize the use of force against Libya (Medvedev allowed Russia’s abstention — the first time a Kremlin leader had allowed the U.N. to authorize a humanitarian intervention. This would come back to bite the United States, as Putin was clearly determined never to let such a thing happen again).

At the same time, however, official Russian attitudes about the United States remained laced with grievance and blame. For instance, Russia asserted that NATO leaders had repeatedly lied about their true intentions and that they in fact viewed Russia as an enemy (which was, at least up until 2014, formally not true). Russia also used the reset era to modernize its military and address the shortcomings that had been exposed in the 2008 Georgia War — cutting its bloated ranks, investing in rapidly deployable forces and innovating and testing its tools of hybrid warfare.

The stage was set for things to quickly sour when Putin reemerged in 2011. After Russia’s parliamentary elections were marred by reports of fraud and voter intimidation, Putin publicly accused the United States (specifically, then-Secretary of State Hillary Clinton) of fomenting protests. Obama responded by signing sanctions legislation into law, speaking out forcefully about Putin’s domestic crackdowns and canceling planned summits.

In the wake of these fraying relations, the Pentagon’s modest efforts to develop constructive military-to-military relations with their Russian counterparts — for instance, exploring joint projects such as counterterrorism — fizzled. Importantly, by this point there were fewer issues on which the United States needed Russian cooperation. By the end of 2016, the U.S.-Russia relationship had devolved to Cold War levels of tension, distrust and hostility.

The Obama administration always thought of the reset with Russia as a temporary diplomatic phase. Its policy accomplishments — on nuclear security, Iran sanctions and Afghanistan — paid dividends for American interests, and Washington traded little to achieve them. So in retrospect, Obama’s error was not the policy itself but in overselling the reset and allowing it to obscure the more nefarious developments in Russian behavior, especially its military modernization and efforts to interfere in European elections (foreshadowing what happened in the 2016 U.S. election). And after Putin formally returned to power in 2012, Obama was too slow to declare the reset over.

Reflecting on this history offers several lessons. First, don’t exaggerate the potential for cooperation with Russia. In this instance, presidents are better off underpromising and overdelivering. As long as Putin remains in charge, there is very little potential for a productive U.S.-Russia relationship, and presidents should set expectations accordingly.

Second, Washington should not be seen chasing Moscow, as though the United States needs Russia more than Russia needs the United States. This was something the Obama administration grappled with, especially during 2015-2016, when then-Secretary of State John F. Kerry was trying to cut a deal over Syria. And it is a trap the Trump administration seems prone to fall into. The United States should not be afraid of isolating Russia or plainly stating that it will work to contain Russia’s aspirations.

Third, regardless of Moscow’s intent, recognize that today there are fewer policy areas in which even “selective partnership” with Russia is essential to achieve U.S. goals. This means that there is less upside to U.S.-Russia cooperation, as well as fewer negative repercussions from discord. In other words, to serve American interests we need to deter Russia from being a disrupter, but we don’t necessarily need it to be a good partner.