This Sunday marks the 25th anniversary of the fall of the Berlin Wall. I grew up against the backdrop of the Cold War. Leonid Brezhnev was the Soviet premier for the first decade of my life. His 1982 funeral was represented the dour pageantry of the Soviet Union to which we had become accustomed. I was in the sixth grade when a Soviet pilot shot down Korean Air 007. In hindsight we learned that it was perhaps the closest the United States and Soviet Union had come to nuclear war in my lifetime. And, as a voracious reader, I grew up reading Cold War thrillers such as Fail Safe, Seven Days in May, On the Beach, and later The Charm School, and I also remember the debates in school about whether or not it was appropriate for kids my age to see The Day After when it first appeared on television. Walking around Northeast Philadelphia where I grew up, many buildings still housed these signs which somewhere along the years thankfully disappeared.

When I had my bar mitzvah back in 1984, like many of my peers, I was “twinned” with a Soviet Jew my age and encouraged to write to him. I quickly received a note back asking me not to write anymore because his family feared for their safety. Teachers and peers, meanwhile, would regularly go and protest Ronald Reagan’s “warmongering” and military build-up in Western Europe. Against the backdrop of all this, there were many who downplayed the importance of freedom even as it was denied to so many. The Soviet Union would be a permanent fixture of our world and that we just had to bargain with what was there rather than what we’d like to see. Cuba might be a dictatorship, but couldn’t we just applaud its health-care system? Maybe the United States was at fault in Nicaragua and the people truly wanted to be in the Communist orbit.

Then Berlin happened. It was my senior year in high school, and what a heady time it was, coming just months after the bloody crackdown in Tiananmen Square. Despite what diplomats, teachers, professors, and news anchors told us, perhaps people really did want to be free. It’s hard to argue with hundreds of thousands clamoring to escape the prison in which their leaders had put them. Whereas many so-called sophisticated Americans had mocked Ronald Reagan for his “evil empire” remarks, those escaping from Soviet tutelage described his moral clarity as a shot of adrenalin to those seeking freedom and individual liberty.

How unfortunate it is, then, that history must repeat, that somehow those in power and those entrusted with American diplomacy have come to once again embrace moral equivalency and shirk moral clarity. We need look no further than Iran. Whereas many U.S. presidents have reached their hand out to the Iranian people, President Obama was the first to substitute a direct outreach to Iranians with instead the legitimization of the Islamic Republic, the regime which so oppresses them.

Part of this might be ignorance of his advisors. When one looks at the histories and explanations of the Islamic Revolution published in English, so many of these were commissioned against the backdrop of revolution by publishers who wanted an answer to how so many in the West were taken by surprise by the Islamic Revolution. The most popular of the resulting books—and those still used in universities—for example, Nikki Keddie’s Roots of Revolution and Ervand Abrahamian’s Iran Between Two Revolutions, treated the Islamic Revolution as the natural apex of Iranian political evolution. It might not have looked it at the time, but such a conclusion was nonsense. The Islamic Revolution was just as much an anomaly, one made possible by a confluence of events ranging from the shah’s cancer, Carter’s bungling, Khomeini’s exile from Iraq, and pure dumb luck on Khomeini’s part. It does a tremendous disservice to the Iranian people to treat the theocracy and regime imposed upon them by Ayatollah Khomeini as a permanent part of the Iranian political landscape.

The outreach Obama initiated led the president to downplay rather than offer moral support to the 2009 uprising inside Iran. Then, in order to grease his outreach, he offered Iran more than $7 billion in sanctions relief at a time when, thanks in part to sanctions, Iran’s economy was fast contracting. And that was even before the price of oil dropped precipitously, well below the level necessary to support the budget which Iranian leaders calculated.

Ronald Reagan ended the Soviet Union by forcing it to bankrupt itself. Obama was offered the same opportunity with a state just as hostile to the United States and chose to throw it a life raft. As we near a quarter century from the Berlin Wall’s fall, we should not kid ourselves by believing that it is somehow sophisticated diplomacy to preserve our adversaries or downplay the aspirations for freedom which peoples chafing under dictatorship hold. It is a lesson Obama and Kerry should consider as they work to cement their legacy on the backs of ordinary Iranians.

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