Is Trump Repeating Obama’s Iran Mistake and Bush’s Iraq Disaster?

Civil War Would Devastate Iran, but That Becomes a Self-Fulfilling Prophecy If the U.S. Doesn’t Push for Managed Transition

President Donald Trump and Secretary of State Marco Rubio at the White House on June 21, 2025.

President Donald Trump and Secretary of State Marco Rubio at the White House on June 21, 2025.

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President Donald Trump is adamant that Israel and Iran must end their 12-day war. He reportedly telephoned Israeli Prime Minister Benjamin Netanyahu to demand that Israel recall bombers en route to targets in Iran as Israel sought to retaliate for an Iranian missile strike on northern Israel.

Trump is sincere about diplomacy. When Supreme Leader Ali Khamenei emerges from hiding, Trump hopes to work with him on a deal to end Iran’s nuclear program. This is the major reason why Trump opposes any Israeli effort to kill Khamenei; to do so would deprive Trump of a partner capable of signing the agreement to surrender the Iranian nuclear program.

When Supreme Leader Ali Khamenei emerges from hiding, Trump hopes to work with him on a deal to end Iran’s nuclear program.

Trump’s actions today are reminiscent of President Barack Obama in the wake of Iranian post-election unrest in 2009. After Khamenei ordered fraudulent election results released to throw victory to the unpopular hardliner Mahmoud Ahmadinejad, Iranians poured into the streets across the country. While there had been protests in 1999 and 2001, the 2009 unrest was the most severe since the 1979 Islamic Revolution.

For more than a week, Obama remained largely silent. Frustrated Iranians chanted “Obama, Obama, ya ba oona, ya ba ma,” Persian for “Obama, Obama, [you’re either] with them or with us.” When Obama did issue a statement, it was milquetoast. Only afterward did Khamenei leak word that Obama had sent letters begging him for talks. Speaking on the thirtieth anniversary of the seizure of the U.S. Embassy in Tehran, Khamenei mocked Obama: “This new President of America said beautiful things. He sent us messages constantly, both orally and written: ‘Come and let us turn the page, come and create a new situation, come and let us cooperate in solving the problems of the world.’ It reached this degree!”

Ultimately, Khamenei did authorize talks, but only on Iran’s terms. Their result was an exculpation of decades of Iranian nuclear cheating and normalization of an industrial-scale enrichment program upon which restrictions would begin to lift this year. Khamenei now hopes to repeat history.

Another analogy looms large. At a February 15, 1991, campaign stop in Ohio, President George H.W. Bush called upon the Iraqi people “take matters into their own hands and force Saddam Hussein, the dictator, to step aside.” They heeded his call and took to the streets.

Bush did nothing initially as Saddam dispatched his Republican Guards to mow down thousands of protestors, though he subsequently created a small safe haven and a larger no-fly zone to prevent millions of Iraqis from fleeing into Turkey. Ultimately, it was the elder Bush’s inaction that bred the cynicism in Iraq that came back to haunt the younger Bush while president.

Ordinary Iranians are aware of Bush’s betrayal of Iraqi Shi’ites and Kurds, and they fear Trump’s desire to pose with Khamenei will come at the cost of even more Iranian lives.

Many officials now trot out the risk of regime change as a bogey to justify inaction.

Many officials now trot out the risk of regime change as a bogey to justify inaction. This is nothing new. European diplomats and even the State Department wrung their hands about allowing Hamas to wither and opposed unraveling Hezbollah’s control over southern Lebanon. Civil war in Iran would be devastating, but that becomes a self-fulfilling prophecy if U.S. reticence leads to a free-for-all scramble rather than a managed transition.

If Trump does not want to be remembered as Obama version 2.0 or George H.W. Bush, rather than preserve Khamenei, he should simply tell him, “Khodahafez” [good-bye].

Michael Rubin is a senior fellow at the American Enterprise Institute, where he specializes in Middle Eastern countries, particularly Iran and Turkey. His career includes time as a Pentagon official, with field experiences in Iran, Yemen, and Iraq, as well as engagements with the Taliban prior to 9/11. Mr. Rubin has also contributed to military education, teaching U.S. Navy and Marine units about regional conflicts and terrorism. His scholarly work includes several key publications, such as “Dancing with the Devil” and “Eternal Iran.” Rubin earned his Ph.D. and M.A. in history and a B.S. in biology from Yale University.
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