The United States’ relationship with Iran is a complex, volatile and deeply frustrating one. This year marks the 30th anniversary of the Iranian revolution, an event seared into the consciousness of many older Americans, who vividly recall television footage of “America Held Hostage,” when 52 people were held for 444 days by radical Islamic students inspired by a fundamentalist revolution in Tehran. The real roots of our estranged relationship with Iran date back more than a half-century: in 1953 President Eisenhower ordered a coup d’état against Iran’s democratically elected leader, Mohammad Mossadeq, and installed Mohammad Reza Shah to the throne. The memory of 1953 played a key role during the revolution, when deep distrust and anger with the U.S led to the Embassy seizure.

Diplomatic efforts have gone awry over the past thirty years. “Death to America” is still a popular chant at Iranian rallies, and Iran loomed large in the infamous “Axis of Evil” formulation by President Bush during his 2002 State of the Union Address. Academics and pundits typically conclude that Iran is a dangerous, rogue state. For instance, Claudia Rosett, a columnist for the Wall Street Journal, echoed the standard, pessimistic line in a recent talk on campus: “Iran supports terrorist organizations, threatens the world with its nuclear program and has a grave human rights record at home.” But this rhetoric, while true, does not offer much to the larger policy discussion: can we engage Iran before it’s too late?

President Obama suggested during the election that he might consider “unconditional talks” with Iran, and in his first presidential press conference, reiterated a new approach: “My expectation is … we will be looking for openings that can be created where we can start sitting across the table, face to face; of diplomatic overtures … to move our policy in a new direction.” It’s still early for Obama, although it may be getting late in the nuclear game. A military attack on Iran, a serious diplomatic effort or some mixture of sticks and carrots are all options that U.S. policymakers are considering. But how effective and realistic are these options? A military attack would have violent ripple effects throughout the region, while diplomatic efforts might lead Iran to produce a nuclear weapon. It may be time for U.S policymakers to consider what was once the unthinkable, but may now be the inevitable: a nuclear Iran.

The Military Option

The U.S does not seem optimistic about a military strike against Iran. In January David Sanger of The New York Times reported that President Bush deflected a secret request by Israel for specialized bunker-busting bombs last year, and also denied an Israeli request to fly over Iraq to reach Iran’s major nuclear complex at Natanz. Top administration officials, Sanger reported, convinced President Bush that any overt attack on Iran would probably prove ineffective, lead to the expulsion of international inspectors and drive Iran’s nuclear effort further underground. Dr. Trita Parsi, President of the National Iranian American Council and author of “Treacherous Alliances: The Secret Dealings of Israel, Iran and the United States,” echoed these sentiments recently at a conference, at Rutgers University: “The capability is simply not there for Israel or the United States to knock out all of Iran’s nuclear sites. Which means that within a few years, Iran would be at the same place in its nuclear development and now looking to create a nuclear weapon for vengeful purposes.” A military attack might also lead Iran to step up efforts to arm terrorist organizations it supports, such as Hamas and Hezbollah, destabilize U.S efforts in Afghanistan and Iraq and also launch long-range missiles into Israel — serious consequences that might lead to a protracted conflict in the region. It seems unlikely that the Obama administration, already addled by a plethora of policy challenges, would seriously consider using military force against Iran.

The Diplomatic Options

Iago Gocheleishvili, an expert on Persian studies at Cornell, suggests that the U.S. must be delicate in its approach to Iran: “There is a serious lack of trust today in Iran of U.S. intentions. The U.S. must first build up a diplomatic relationship, before asking Tehran to concede its nuclear program.” This distrust has deep-felt, historical precedent and was only heightened during the Bush administration. In 2001, for example, James Dobbins — the Bush administration’s first envoy to Afghanistan — worked closely with Iranian policymakers to establish and secure a successor to the Taliban regime. “Iranian representatives were particularly helpful,” Dobbins wrote in a 2007 Washington Post article. And yet, only a few months later, President Bush designated Iran as part of the “Axis of Evil,” a message that Professor Gocheleishvili says sent shockwaves through Tehran: “It once again showed Iran that they could not deal with America, and that they were better off with a hardliner like Mahmoud Ahmadinejad in power.”

Dr. Parsi offers a more nuanced take on negotiations with Iran: “A step-by-step approach to negotiations has almost never worked in the Middle East. One critical problem with the Oslo Accords, for example, was that the peace plan simply took too long to develop.” A more pragmatic approach, Parsi said, might be in modeling the success of the Camp David Accords of 1979, when Israeli foreign minister Moshe Dayan put Israel’s cards on the table at the onset of discussions. “We are willing to give you back the Sinai,” Moshe Dayan told Egyptian President Anwar Sadat. “Now let us figure out how we can do that.”

But exactly which cards does the U.S have to negotiate with Iran? Iran’s leadership has survived under tough economic sanctions, and without a serious threat of U.S military intervention, there does not seem to be any real incentive for Iran to abandon its nuclear program. “Iran is a Shiite island surrounded by threatening Arab neighbors, a large U.S presence in Iraq, and Israel,” Professor Gocheleishvili said. “A nuclear bomb would make Iran a major regional player. It won’t be very easy for the U.S. to convince them to give up that power card.”

President Bush failed to weaken Iran’s position; his ideological approach shunned potential allies and sparked resentment in the Muslim world. President Obama offers a fresh start on diplomatic engagement, but one that might take years to develop any real momentum. The administration is expected to name Dennis Ross, a longtime Middle East peace negotiator, to a senior post handling Iran. Ross is a good choice, and he should signal U.S. willingness to compromise and provide incentives for Iranian cooperation. But the sad truth is this: We have failed to face the music on Iran’s ambition ever since American’s were paraded in blindfolds before the world some three decades ago. And now, as the clock nears midnight, the question must be redefined, lest we fall too far behind the curve again: How is the United States going to deal with a nuclear Iran?