On February 27, Boris Nemtsov, a former Russian deputy prime minister and a liberal opponent of Russian President Vladimir Putin, was shot dead in the shadow of the Kremlin. It wasn’t the first time a Russian figure who ran afoul of Putin paid the ultimate price—think Sergei Magnitsky or Anna Politkovskaya—but it was among the most brazen attacks, or at least the most brazen attack that didn’t involve polonium. Unknown assailants killed Nemtsov, a critic of the Russian invasion of Ukraine, just two days before a major opposition rally. Any doubt that Vladimir Putin is anything but a cold, calculating psychopath, an aggressive despot who seeks not Russian greatness, but rather his own unquestioned power, should now be put to rest.

Hillary Clinton rose to prominence not on her own merits as an elected leader, but rather as a first lady. She might be smart and talented, but her path to power was not her own. Granted, she leveraged her prominence to run and win a Senate seat in New York, but she approached the office with extreme caution and simply bided her time; she certainly will not go down as a great legislator. After surprising no one and running for the presidency in 2008, she got her chance when President Barack Obama appointed her to be his secretary of state. It is chiefly the legacy of these four years in office that provide the only window into Clinton’s executive experience and policy judgment.

Hindsight is always 20/20, but few secretaries of state appear to have been so quickly proved wrong on the major initiatives they oversaw. Like it or not, Clinton’s foreign-policy legacy—the experience she needs to prove that she is worthy of answering the 3 a.m. phone call—rests upon her tenure at the State Department. And it is here that the Russian reality might come crashing down upon Clinton’s presidential ambitions.

President Obama took the Iran issue as his own—asking the Iranian leadership figuratively to unclench its fist—leaving Clinton in charge of Russia. Clinton shaped and oversaw the so-called “reset.” The conceit of the reset was the belief on Obama and Clinton’s part that their predecessors had mishandled the Russian relationship and allowed it to derail. George W. Bush was far from perfect on the issue—his claim to have looked into Putin’s eyes and seen his soul showed poor judgment and misplaced trust—but he quickly calibrated his policies to reality as the real Putin showed through. Clinton’s reset at best reflected a willingness to forgive and forget the Russian occupation of Georgia and, at worst, showed a complete ignorance of Putin and his ambitions.

Had Clinton learned from her mistakes, she might not be tied to Putin today. But, even against the backdrop of Russia’s invasion of Ukraine, Clinton insisted that her reset policy was a success, that it somehow benefited the United States’s security and position in the world. Alas, the opposite is demonstrably true. Russia is far more aggressive today than it has been in decades. Russian bombers not only probe NATO defenses in Europe, but also may soon patrol the Caribbean and Gulf of Mexico.

Then, of course, there was the new Strategic Arms Reduction Treaty (START). In order to win congressional approval for a deal riddled with holes, the State Department withheld information from Congress which detailed Russian cheating on previous agreements. Clinton’s point person on the new START was her undersecretary of state for arms control and international security affairs, Ellen Tauscher. Tauscher subsequently left the State Department and joined the Atlantic Council, where she sought to further the reset with an initiative called “Mutually Assured Stability,” a silly name for an idea that treated Russian ambitions naively. There is no stability when the Kremlin sniffs weakness. What was incredible about Tauscher’s project was that she accepted Kremlin money to underwrite it. The Kremlin founded the Russian International Affairs Council (RIAC) to act as its representative in the NGO world. Clinton had hundreds of staffers, and dozens claimed to be her close aides, so can she really be held accountable for what Tauscher did after leaving the State Department? Normally, the answer would be no. But Clinton has since brought Tauscher back as a key aide in one of the shadow groups organizing her campaign. That suggests Clinton is doubling down on her embrace of Russia even as Putin shows his true colors.

Few presidential elections revolve around foreign policy. Americans tend to vote with their wallets. But 2016 may be an exception: Obama’s diplomatic and national-security strategy had now been tried and found wanting. Obama did not cause the Arab Spring, but his belief in leading from behind allowed wildfires in Libya and Syria to spin out of control. The Russian invasion of Ukraine has reinforced a malaise not seen since the Carter years. Add into this mix that Clinton, if she runs, will have to run on her State Department tenure and it seems evident that foreign policy will matter in 2016. If Clinton cannot admit an error, that’s bad enough. If she truly believes her ideas and actions on Russia were to the benefit of international security, then that suggests a far greater question of judgment.

The more Putin embraces the paranoia and worldview of former Soviet Premier Josef Stalin—a comparison which will only be highlighted by Nemtsov’s murder—the more Clinton may find her State Department tenure not to be her greatest asset, but instead her Achilles’ heel.

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