In March 2003, senior U.S. diplomats flew to Geneva to meet with Iran’s then UN ambassador (now foreign minister) Mohammad Javad Zarif. Their agenda was straight forward: Win Iran’s pledge not to interfere in Iraq. Zarif readily agreed. Two weeks later, Operation Iraqi Freedom began. Two thousand Iranian-trained militiamen flooded into Iraq and, over subsequent years, Iranian weaponry or proxies murdered hundreds of Americans. Zarif either lied outright or exaggerated his ability to make firm commitments to which all Iranians would adhere.

Nevertheless, on September 27, 2013, President Barack Obama announced that he had spoken on the phone with Iranian president Hassan Rouhani, and suggested he could trust that the Iranian leadership. “Iran’s supreme leader has issued a fatwa against the development of nuclear weapons [and] President Rouhani has indicated that Iran will never develop nuclear weapons,” Obama said.

Fast forward twenty-one months. As diplomats from Iran, the United States, Russia, China, France, Germany and the United Kingdom meet to try to finalize a nuclear accord, a final stumbling block has become the requirement that Iran reveal its past nuclear weaponry work. When South Africa forfeited its military nuclear program in 1991, the International Atomic Energy Agency (IAEA) required it come clean on its past work in order to account for all materials. Secretary of State John Kerry, who once made this IAEA demand a redline, has now reversed U.S. policy, saying Iran needn’t disclose its past work since “what we’re concerned about is going forward.” Privately, diplomats explain they want to give Tehran a way out to avoid humiliating Supreme Leader Ali Khamenei. After all, if Khamenei banned nuclear-weapons work, then forcing Iran to explain past activities identified by the IAEA such as experimenting with nuclear bomb triggers and firing systems would expose Khamenei as a liar.

As for Rouhani, in February 9, 2005, he gave a speech in Mashhad during which he reflected on his fifteen years as head of Iran’s Supreme National Security Council. He outlined the history of postrevolutionary Iran’s relations with the United States and argued that at every critical juncture, Tehran had bested Washington. The reason? Surprise: Iranian officials would lull their American counterparts into complacency, and then deliver a knock-out blow.

If reports from intelligence agencies, the IAEA and news organizations suggest that Iran cannot be trusted, then why is Obama so willing to gamble U.S. and Middle Eastern security on a leap of faith?

The problem isn’t simply Iran. U.S. soldiers spend more time getting reprimanded by sergeants, more time in the classroom going over past campaigns and more time discussing after-action reports than they often spend in the field. The reason is simple: By identifying past mistakes, they can avoid repeating them. In the last sixty-five years, however, U.S. diplomats have never conducted a single lessons-learned exercise to assess past diplomacy with rogue regimes, identify mistakes made and suggest new strategies moving forward. It’s that old adage (falsely) attributed to Albert Einstein: Insanity is taking the same action repeatedly and expecting different results each time.

Hossein Mousavian, a nuclear negotiator alongside Rouhani during the 1997-2005 Mohammad Khatami administration, bragged at the time that Tehran had “managed to make far greater progress than North Korea” in its nuclear talks. Despite the Agreed Framework signed in 1994 meant to prevent North Korea’s nuclear breakout, today the hermit kingdom is a nuclear power. When North Korea becomes an example to emulate rather than a regime to condemn, something is wrong. And yet, Kerry staffed his team with alumni of the North Korea talks without ever asking them to identify if and where they made mistakes.

The same pattern of talks absent introspection holds true with the Taliban. Obama made talking with the Taliban a central pillar of his strategy to draw down U.S. forces in Afghanistan. But he never acknowledged that the Clinton administration had talked with the Taliban on more than thirty occasions between 1995 and 2000. The Taliban had promised to close terror training camps and keep Bin Laden under control. The 9/11 terror attacks exposed the Taliban as liars, and yet U.S. diplomats now negotiate not only with the Taliban, but with some of the very same individuals, never demanding an explanation to past insincerity.

Simply put, once administrations begin high-profile diplomacy, they too often will concede anything to keep hope alive. Tehran, like Pyongyang and Kandahar before it, senses desperation and understands the American political calendar. It knows if it digs in its heels, the White House will take a bad agreement over no agreement, regardless of Congressional unease. In effect, Obama and Kerry have become gamblers willing to risk everything just for one more pull of the slot machine lever. Unfortunately, when desperation trumps dispassion, the house—in the Islamic Republic of Iran—will always win.

Michael Rubin is author of Dancing with the Devil: The Perils of Engaging Rogue Regimes (Encounter, 2015).

Image: Flickr/Center for American Progress Action Fund