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Advantage: Iran

Does the U.S. stand a chance against Tehran, the nimble, canny free agent of nuclear negotiations?

Nobody knows how the Iranian nuclear dilemma is going to end. A good deal, a bad deal, no deal, a U.S. or Israeli military strike -- or none of the above? But amid all the uncertainty, at least one thing seems pretty certain: The mullahs are playing three-dimensional chess while the United States is playing checkers.

This is not to say that the Iranians are diplomatic and strategic geniuses. After all, if they were that clever, they wouldn't be reeling under the impact of nation-crushing sanctions that are destroying their economy. Nor would everyone's favorite mullah -- President Hasan Rouhani -- be sending Rosh Hashanah tweets to all his would-be Jewish friends.

The checkers reference is also not meant to suggest that the Obama administration is clueless about how to deal with Iran. While the president's handling of the Syrian chemical weapons issue did at times resemble a Marx Brothers movie, the administration knows the stakes on Iran are higher -- and that, precisely because of Syria, it must be more disciplined, focused, and deliberate.

Yet Iran has certain natural advantages that the United States lacks. This doesn't invariably mean the United States will lose and Iran will win at nuclear roulette. But it does mean that Tehran can be far more agile, devious, and strategic in its quest for a nuclear weapons capacity than Washington can be in its effort to stop it.

Here are brief explanations of these important advantages.

  1. Great Powers Versus Small Tribes

Big doesn't always translate into smart and effective, and small doesn't necessarily mean weak. The Middle East is littered with the remains of great powers that wrongly believed they could impose their will on small tribes.

Compelling and coercing nations not to do something they deem vital is no easy matter. The record, as my Foreign Policy colleague Micah Zenko points out, isn't all that great. Big global powers like the United States have many things to do, and they are distracted and tire easily. Smaller ones like Iran that live in a dangerous neighborhood can't afford to do the same. They're focused intensely on just a few things: physical security, survival of the regime, maintaining religious and national identity, historical grievances, wounding and trauma, and fear of bigger powers. They become quite adept at manipulating and maneuvering around these larger powers to achieve their goals, both because of their will and because of their knowledge of the real estate: They know their region's back alleys, sand traps, and complicated ways.

In recent years, the United States has come to Iran's neighborhood all too often and with too little knowledge of the landscape. With our overwhelming military power and technological superiority, we can remove leaders and weaken groups hostile to our interests. But the locals can and do make us pay big time. (See: Lebanon, Somalia, Afghanistan, Iraq.) A decade after we've left, all our schemes and dreams won't have changed much on the ground. Two decades later, if locals remember we were there, it usually isn't fondly.

Iran has been particularly deft in capitalizing on these sorts of U.S. mistakes. The invasion of Iraq and Afghanistan weakened the Taliban and eliminated Saddam Hussein -- two of Iran's adversaries -- and bolstered its regional standing. Iran has also maneuvered deftly, and thus played well, in regional developments like the Syrian crisis. It has backed President Bashar al-Assad, exploited his regime's Hezbollah connection, and managed along with the Russians to keep the regime afloat. The U.S.-Russian agreement on chemical weapons has also furthered the Iranian goal of legitimizing the Syrian leader and has raised questions in the minds of the mullahs about whether we are prepared to use military force in the Middle East.

Finally, thanks largely to its smaller, nimbler status, Iran has withstood sanctions, political isolation, cyberwar, and the efforts of three successive U.S. administrations to prevent it from acquiring a nuclear weapon. Indeed, in 2013, Tehran is closer than ever to attaining the capacity to weaponize within a relatively short period of time. And who knows? They may be even nearer than we and the Israelis realize to crossing that threshold.

  1. Iran Knows Its Own Mind. Do We Know Ours?

We really don't know what the Iranian game is. Are we on the cusp of a new era in the U.S.-Iranian relationship with a deal on the nuclear issue that will lead to a broader regional modus vivendi? Or is the Rouhani diplomatic offensive designed to buy time, probe for weakness and division in allied ranks, neutralize the Israeli military option, and reinforce through charm and sweet talk an American president's already strong preference for diplomacy over war?

Nor does the United States fully grasp its own game. There is tremendous uncertainty about what, in the end, to do about Iran's quest for a nuclear weapon. Do we bomb if diplomacy fails? Do we contain? What do we do if/when Israel decides it must use force? Our policy oozes indecision. And it shows.

The mullahs are indeed smart and canny, and unlike U.S. leaders, they probably know their own mind on the nuclear issue. No matter how real Rouhani may be as a reformer and as a legitimate expression of a popular Iranian desire for change, he's still not the guy in charge. And the guy who is fashions himself the supreme leader of a truly great and historic nation confronted by an America and an Israel that seek to keep Iran down and to deny the country its rightful place in the region and the world. Iran is a country driven by a profound sense of insecurity and entitlement -- a very bad combination of personality traits in an individual, let alone in a nation.

Indeed, Ali Khamenei and his conservative-cum-revolutionary, security-minded cronies may well regard the quest for a nuclear weapons capacity as a basic right, part of their country's identity as a power, designed to bolster Iran's status -- and as a hedge against regime change and as cover to wield regional influence.

The pursuit of Iran's nuclear ambitions has been a national goal for quite some time. Indeed, had the Shah not been overthrown, Iran might already have been a nuclear state. For Iran to completely abandon that goal or to allow the United States to impose restrictions that would make it impossible to pursue it again in the future seems hard to imagine.

  1. The Rouhani Phenomenon

The emergence of Rouhani is the perfect play against the United States, because his election as president really does reflect reformist tendencies within the Iranian public and polity. Sanctions are ruining the economy and hold the potential to create serious popular discontent. Why not send abroad a smiling, attractive, and forthcoming president who can tone down the anti-Israeli rhetoric, accept the Holocaust, and deny Iran has a nuclear weapons program, even while Tehran continues to pursue said program?

The Iranian leadership can lie, dissemble, and pursue this two-track strategy without blinking an eye and without fear of any domestic backlash, all in an effort to see what kind of sanctions relief it can achieve and what it has to pay for it. If the price isn't right, it can recalibrate, turn on a dime, and effortlessly return to the hard-line rhetoric of Rouhani's predecessor.

For Obama, investing in Rouhani thus means risking being made to look the fool should the process reach the point where the mullahs determine that what we're offering isn't sufficient to meet their needs. And, while this budding relationship congeals, the U.S. president is in the uncomfortable position of having to explain every negative Iranian statement or action. Yet Iran has positioned Rouhani as a risk the United States feels it must take.

  1. Negotiating for Whom?

Iran is a free agent in negotiating with the United States. We aren't in as enviable position. Whatever political constraints Khamenei faces, they aren't nearly as narrowing as ours. Between Congress and U.S. allies -- Israel but also Saudi Arabia -- the U.S. position must take into account an array of suspicions and fears, some of them at times competing with each other.

Congress is critical for sanctions relief and for the domestic consensus required for any foreign-policy initiative, particularly one as big as this. And the notion that the Obama administration will somehow have a free hand to ignore Israeli needs strains the bounds of credulity to the breaking point. As Undersecretary of State Wendy Sherman conceded the other day, no deal is better than a bad deal. A bad deal would be one that leaves Israel angry, suspicious, and aggrieved and Iran able to quickly re-create a nuclear breakout option should Tehran suspend or abrogate the agreement.

These realities will not only reduce U.S. flexibility; they also afford Iran a powerful political and propaganda point to argue that the United States isn't negotiating on the merits of the nuclear issue but is allowing politics to shape its positions. It also takes Iran off the hook for responding seriously to what the United States offers. Indeed, the Iranians have undoubtedly figured out that Obama will be quite risk-averse when it comes to offering major concessions. That frees the mullahs from their need to be forthcoming as well.

Let's hope that the mullahs haven't concluded, too, that Obama will be risk-averse when it comes to a military option, should diplomacy fail.

  1. Time: Ally or Adversary?

U.S. presidents and government negotiators measure their lives in four- and eight-year increments -- that is, the terms of administrations. Iran, by contrast, plays the long game, the generational game. Sure, Iran wants sanctions relief. But it can wait if it doesn't get exactly what it wants.

In addition to the limited time frame of his second term, Obama is up against two clocks that are ticking down to a place he'd rather not be: a military option. First, there's the clock showing that Iran is nearing the point of no return -- the much-feared breakout capacity. That, in turn, influences the second clock: Israel's own timeline for making the agonizing decision about its military options.

In a way, too, the Rouhani charm offensive may have accelerated matters for Washington. By elevating the level of negotiations -- opening new channels to both the U.S. president and the secretary of state -- it will be harder, not easier, for the United States to drag things out. Before, in the P5+1 talks in Almaty, Istanbul, and Moscow, we were on mullah time; now, we're on fast-tracked Washington time. After all, once the president at the U.N. General Assembly, in front of the whole world, directs his secretary of state to manage negotiations, it's hard to go back to business as usual.

Maybe the moment of decision is coming. Maybe not. If negotiations really are serious and a deal, however imperfect, is in sight, time will be less of a U.S. concern going forward than it is now. If things don't go well at the table, however, then at some point it will be time to stop pretending that negotiations can answer the mail -- and to acknowledge how Iran's generational game could play out.

Iran doesn't want an Israeli strike, let alone a U.S. one. But it may well calculate that, if it doesn't stick a nuclear weapons program in President Obama's eye, the United States won't strike. As for the Israelis, the mullahs may well take their chances and wager that the temporary setback to their nuclear program would be outweighed by the political benefits they might gain from an Israeli strike.

It's a roll of the dice. But Iran, with all its advantages over the United States and its allies, just might take the risk. Indeed, the message from Tehran might be: Come and get us. And, by the way, welcome to the neighborhood.

BEHROUZ MEHRI/AFP/Getty Images

Reality Check

Why Bibi Should Rest Easy

Obama is not going to sell out Israel in an Iran deal.

Former Israeli Prime Minister Ehud Olmert once told me that all Israeli prime ministers sleep with one eye open. Israel is a tiny country in a dangerous neighborhood. Worrying is a big part of the job description.

Prime Minister Benjamin Netanyahu has already expressed serious concern about wily Iranian mullahs bearing gifts. So when he sits down with Barack Obama on Monday at the White House, should he be worried that the president is planning to cut a deal with Iran at Israel's expense?

Absolutely not. Either there will be a very good deal that will take care of both U.S. and Israeli concerns on the nuclear issue, or there will be no deal at all. And here's why.

First of all, the president worked hard to reset his relationship with Netanyahu and Israel this past year, so he isn't going to undo the progress he's made without a compelling purpose. Tensions with Israel during his first term not only brought zero benefits on foreign policy, but actually became gratuitously harmful, gave Republicans a chance to hammer him, and raised concerns within his own party about his pro-Israel credentials. Given his domestic travails and the 2014 midterms, the last thing he wants or needs is a fight with Israel.

For another thing, in his recent address to the U.N. General Assembly, the president identified two key foreign policy priorities in his second term: Iran and the Palestinians. Israel sits at the nexus of both. Managing, let alone resolving, those issues requires close understandings with Israel. To put it more bluntly, if Obama is to have any hope of avoiding war with Iran on the nuclear issue, he will have to keep Israel close. And any chance that Secretary of State John Kerry may have to push the peace process forward depends on getting along with Netanyahu, not alienating him.

Then there is the fact that Hasan Rouhani isn't Anwar Sadat. And Iran isn't Egypt in 1977, suing for peace with Israel -- or the United States for that matter. The mullahs aren't going to charm anyone for very long, let alone transform public attitudes in Israel or America without significant and tangible deliverables. And that's not going to happen quickly or easily given the withholding nature of the Supreme Leader, who may actually see benefits in keeping the U.S.-Iranian relationship in a kind of managed tensions.

Finally, Obama simply can't afford to be played the fool by Teheran. It's true Iran plays three-dimensional chess in its foreign policy while we seem to play checkers. But the alert level on the Iranian charm offensive is incredibly high, and Obama is likely to be cautious and risk averse when it comes to the nuclear issue. Besides, there's no issue that unites Congress like its mistrust of Iran. The administration would be hammered for showing signs of weakness without tangible and compelling concessions from Teheran. And Obama himself has staked much of his personal credibility on stopping Iran from acquiring a weapon. He has a huge incentive to make a deal -- but only if it can credibly accomplish that end.

Netanyahu does face significant challenges. But neither has much to do with Barack Obama. First, the Israeli prime minister confronts a tough and wily Iranian regime that's close to crossing the nuclear threshold but is probing to see whether it can get sanctions relief without giving up all of its nuclear gains. Indeed, it's far from certain that despite the pain of sanctions, the Supreme Leader is in any hurry to drop the program's military aspects without major concessions from the United States.

And then there's Netanyahu himself -- a man who can also be his own worst enemy when his suspicions and inflexibility get the better of him. Whether the Iranian charm offensive is a trap or an opportunity isn't clear.

But, regardless, right now Israel needs a strong, confident, pragmatic hawk to deal with that dynamic -- a leader who is suspicious of Iran's opening, but who's also open to a deal, to probing whether what Iran is selling is real, marketable, and profitable for both sides. Israel needs a leader who's willing to trust and verify the motives of its close ally and then, if an agreement makes sense, to concede what he must. If -- and it's a galactic "if" -- an agreement that ends the military aspects of Iran's nuclear program with comprehensive inspections is to be reached in return for dismantling of sanctions and Iran's right to enrich uranium for civilian use, everyone -- the Iranians, the Americans, and the Israelis -- will need to concede something significant.

The art of diplomacy is having the courage, wisdom, boldness, and prudence to determine whether the price you have to pay is worth what you're getting in return. It's a weighty decision indeed, particularly when the alternatives seem to be an Iran with a bomb or bombs over Iran.

Uriel Sinai/Getty Images