The Obama administration has always seemed to have trouble managing even one foreign-policy crisis at a time. But the opening of the next stage of the P5+1 nuclear talks with Iran in the same week that Russia, the West’s nominal partner in trying to negotiate a resolution of the nuclear question with Tehran, is annexing Crimea is posing a particularly difficult dilemma for the administration. After all, President Obama and Secretary of State Kerry have been counting on Moscow to back up the West’s efforts to get the Iranians to give up their quest for nuclear weapons or at least not to sabotage either the talks or the sanctions on the Islamist regime. But with the U.S. and the European Union contemplating sanctions to punish the Putin government for its aggression against Ukraine, how can they possibly expect the Russians to act as partners in an effort to pressure Iran in the exact same manner?

Those worries are the conceit of a story in today’s New York Times in which an anonymous “senior American official” could do no better than to express the “hope” that the defiant Russians would not “put these negotiations at risk.” But the problem with the administration’s approach to the Iran talks goes deeper than merely it being bad luck that the Ukraine crisis has happened at just the moment when the president was hoping to swing a deal with Tehran. Even in the best of times, Russia’s equivocal attitude toward pressuring Iran was always a liability to the Western negotiators. But the open breach between Russia and the West over its seizure of Crimea makes an agreement that would actually prevent Iran from getting a bomb in the long run even more unlikely than it was before. Rather than re-evaluate an approach that was already rooted in weakness, the president and Kerry are apparently determined to stick with a losing hand. If Iran’s negotiators weren’t already confident about their ability to take Obama to the cleaners in the talks, they are now.

The presence of Russia and China in the group negotiating with Iran was always Iran’s ace in the hole in the talks. While both countries have expressed their opposition to the prospect of an Iranian bomb, their role in this diplomatic equation was always complicated. Russia has been a major supplier of nuclear technology as well as arms to Iran, including anti-aircraft missiles that would make a strike on their facilities even more difficult. Russia also has an extensive trade relationship with Tehran. Meanwhile China is the ayatollah’s leading trade partner in the vital oil sales that keep the Islamist regime afloat financially. Under the most favorable circumstances for diplomacy, those factors created an even greater conflict of interest than the strong trade ties between America’s European allies and Iran.

But Russia’s ties with Iran are also connected with Putin’s desire to recreate the old Soviet empire. The Bashar Assad government in Syria, Moscow’s principal Middle East ally, has only been kept in power because of Iran’s intervention in the civil war in that country. Though the Obama administration has always been beguiled by its hopes for a “reset” with Russia, the guiding principle of Moscow’s foreign policy in the Putin era is its desire to expand its influence abroad at America’s expense. Though Putin would rather not see a nuclear-armed Iran on the southern border of the old Soviet Union, his commonality of interests with Tehran always threatened to overshadow any desire on his part to cooperate with Western diplomacy.

However, getting Russia to be part of the international coalition against Iran was always a priority for the administration. In theory, this was a sensible decision since without Russia as well as China sanctions were never going to work against Iran. But Washington’s dependence on them also forced those sanctions to be watered down. It was also part of the reasoning that led Obama to conclude that it was smarter for the West to give up its military and economic leverage over Iran in order to conclude an interim deal that gave Iran far more than it gave up last fall.

All of this means that Iran is in an even stronger position vis-à-vis the West in the talks than the already formidable stance it was able to sustain in earlier rounds of diplomacy. Secure in the knowledge that Russia will never agree to a re-imposition of the sanctions that were dropped in November or impose tougher ones (such as the program Congress is still considering) that would shut down Iran’s oil trade for good, Tehran can simply stand its ground in the talks. That means that if President Obama wants an agreement—and he’s already demonstrated that he’s willing to do just about anything to get out of his promise to stop Iran’s nuclear quest—he’s going to have to let Tehran keep its nuclear program and give up the sanctions.

But those inclined to blame Obama’s weak position on Iran on bad luck, bad timing, or Russian aggression are mistaken. The diplomatic path chosen by the administration was always dependent on Russian goodwill that was never likely to be forthcoming. The flaws in the P5+1 formula were already there long before Putin seized Crimea.