Will Khamenei face a similar fate to Gaddafi, Assad and Maduro?

Iran is being advised by regional powers to negotiate with the US to stave off military action, but that would mean Iran walking back its red lines. Will it capitulate or hold its ground?

Will Khamenei face a similar fate to Gaddafi, Assad and Maduro?

In 2011, amid heightened anti-government protests in Libya, a Western intelligence official delivered a message to Moussa Koussa—a key security advisor to then-president Muammar Gaddafi: your leader must leave power if he wants to spare his country from further violence. Gaddafi chose to fight and ended up being savagely tortured and executed.

That same year, a very similar scenario played out in Syria. As anti-government protests swept the country, a Western official also met secretly in a European capital with an envoy of Bashar al-Assad, conveying an offer of resignation to initiate a political transition that would address protesters’ demands while preserving state institutions. Like Gaddafi, Assad similarly rejected the ultimatum.

At the end of 2013, further counsel arrived, this time from Iranian Supreme Leader Ali Khamenei and Russian President Vladimir Putin. Assad was urged to surrender chemical weapons to stave off US strikes intended to accelerate the collapse of his regime. He agreed to trade his chemical arsenal for survival.

Unlike Gaddafi, Assad managed to endure due to the external help he received from Russia and Iran. And even when his regime fell in December 2024, Putin intervened again to spare him from a death akin to Gaddafi's. He is now living in exile in Russia, where Putin has promised to keep his word and protect him.

In Venezuela, Trump offered Nicolás Maduro to step down from power, and be exiled to Türkiye. Maduro also declined, and now the Venezuelan president sits in an American prison after he was snatched from his Caracas residence in a US military operation at the beginning of the year.

For decades, Iran has played for time, putting regional militias at the forefront of the battle with the US and Israel. But now it has to face the music.

Stark choice

Is such an offer being made to Iran? If so, Tehran faces a stark choice: make a deal or face the wrath of US military action. The US and Israel want Iran to halt its nuclear enrichment; hand over its 400kg-enriched uranium stockpile, dismantle its ballistic missile programme; and stop its support for regional militias stretching from Lebanon to Iraq and Yemen. Anxious to avoid chaos and turmoil, regional powers are urging Iran to negotiate.

For its part, Iran says it can make concessions on its nuclear file and even surrender its current stockpile of enriched uranium, but it has drawn a red line on its ballistic missile programme and support for regional militias.

Whether Trump will accept such terms remains to be seen. The same parties were in the same situation seven months ago, negotiating over Iran's nuclear programme, but in the middle of discussions, Israel launched a surprise attack on Iran, and the US ended up joining in towards the end of what became known as the 12-day war.

For decades, Iran has played for time, putting regional militias at the forefront of the battle with the US and Israel, to avoid a direct confrontation and preserve the Islamic Republic. But now it seems that it's crunch time, and it has to face music head-on: will Iran's Supreme Leader compromise or refuse to surrender like Gaddafi, Assad and Maduro? And could Iran's Supreme Leader meet a similar fate to any of these toppled presidents? Time will tell.

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