It may sound cloak-and-dagger, but that's how a lot of delicate diplomacy is done. Back-channel talks opened the way to the U.S. relationship with China in 1972, the Israeli-Palestinian peace agreement in 1993 and other lesser breakthroughs.
So Ross and Undersecretary of State William Burns have been huddling with Iran experts and European diplomats to formulate a strategy.
The administration hasn't decided exactly what form the message should take. It could be a personal letter from Obama to Khamenei, or an oral communication from one diplomat to another. However it's conveyed, it will be a diplomatic version of the "extended hand" Obama offered in his inaugural address. In effect, it will say: We are ready to talk. Just name a time and place.
Beyond that, the message may be notable for what it doesn't say. It may not even mention the touchiest issue between the two countries: nuclear weapons. Obama's goal at this point is to get talks started, not to define their substance.
European diplomats have pushed for Obama's message to Khamenei to explicitly renounce any U.S. ambition of "regime change," a basic condition for talks in the Iranians' eyes. That's an assurance the Bush folks couldn't bring themselves to make, even after they finally recognized that ousting Khamenei was beyond their grasp. It's not yet clear how the Obama team will handle that issue.
One subject of debate is just how tough the U.S. should be. Before assuming his current post, Ross advocated a fairly hard line, writing in a 2007 New Republic article that "penalties, more than [positive] inducements, are the key to altering the Iranian position." But one European diplomat who met with him last week argued that new sanctions should be delayed at least through the spring to allow negotiations a better chance to get off the ground.
On one key point, everyone agrees: Negotiations must be with Khamenei, the cleric who is Iran's supreme leader, not with President Mahmoud Ahmadinejad or any lesser official.
So will Khamenei bite? The Iranian leader has sent contradictory signals. He has said that Iran has never opposed talking with the U.S. as long as the two countries were on an equal footing. But he also has denounced Obama for supporting Israel and for following "the same wrong path" as George W. Bush.
The strongest impetus for Khamenei to engage is his country's economic crisis. With an official inflation rate of 26% and an unemployment rate of more than 12.5%, Iran has a desperate need for foreign capital and technology to boost oil production. The global economic collapse has had at least one silver lining: It has deprived Iran of the economic power it enjoyed when oil sold for $147 a barrel. Now, with oil below $50, Iran's government is running a deep budget deficit -- and Tehran has a harder time selling bonds than Timothy Geithner.
But even if Iran comes to the table, agreement may be difficult. The U.S. and its allies want Iran to stop enriching uranium and put its nuclear energy program under tighter international control. Iran wants an end to the economic sanctions that have been imposed by the United Nations, the U.S. and the European Union.
But that's not all. Iran wants the United States to stop supporting Iranian rebels in the southern province of Baluchistan. (The CIA has denied funding the groups; the Iranians don't believe the denial.) The United States wants Iran to stop supporting Hamas in the Gaza Strip and Hezbollah in Lebanon. Both countries are involved in Iraq and Afghanistan, and both want to reduce the amount of opium and heroin that Afghanistan exports.
If negotiations get underway, the biggest worry is that the Iranians will try to use the talks as a way of running out the clock until their nuclear program is more advanced. That's what frustrated European diplomats believe Tehran did to them over the last five years. So one of the toughest parts of the U.S. strategy will be setting a deadline by which the Iranians must move -- and sticking to it.
Two other potentially difficult scenarios face the United States if Iran agrees to negotiate. One is if the most moderate candidate in Iran's presidential election, Mohammad Khatami, wins. If he were to take office, it would be harder for Obama to walk away from negotiations, even if they were going in circles. A second is if Iran opts for what nuclear experts call the "Japanese option" -- developing a technological capability to produce nuclear weapons without actually making them. That could keep Iran within international rules, making it difficult for the U.S. and its allies to crack down.
During last year's presidential campaign, Obama was criticized by opponents (including Hillary Rodham Clinton) for offering to negotiate with Iran without preconditions. It's now clear that he was right all along; without a more open U.S. approach to Tehran, the international effort to put pressure on the Iranians had reached a dead end. But getting talks started will be only the first hurdle; Iranians pride themselves on their negotiating skill. Obama's real test may be this: If the talks don't make progress, is he willing to walk away from the table?