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Breaking: How to negotiate with Iran , by an ambassador who succeeded — thetimes.com

created: Mar 28, 2026, 06:27 PM
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Matthew Gould says the regime in Tehran has a high pain threshold and a history of using aggression as leverage — but also flaws that Trump could exploit P resident Trump considers himself the world’s best negotiator. He even (sort of) wrote a book about it. But he may be about to meet his match in the Iranian regime. It is looking increasingly likely that some sort of negotiation will take place between the two sides of this war, despite the US and Iran’s contradictory statements in recent days about the state of talks. When they do happen, Trump is likely to find any negotiations infinitely more frustrating than the conflict that has preceded them. The Iranians have no concept of win-win: for them a successful negotiation is one in which the other guy is left crying. If the other party i

Matthew Gould says the regime in Tehran has a high pain threshold and a history of using aggression as leverage — but also flaws that Trump could exploit P resident Trump considers himself the world’s best negotiator. He even (sort of) wrote a book about it. But he may be about to meet his match in the Iranian regime. It is looking increasingly likely that some sort of negotiation will take place between the two sides of this war, despite the US and Iran’s contradictory statements in recent days about the state of talks. When they do happen, Trump is likely to find any negotiations infinitely more frustrating than the conflict that has preceded them. The Iranians have no concept of win-win: for them a successful negotiation is one in which the other guy is left crying. If the other party is happy at the handshake, then clearly you haven’t squeezed them enough. I experienced this approach myself, as the UK’s deputy ambassador to Iran, in 2004, when the regime seized a group of British military personnel on the Shatt al-Arab waterway between Iraq and Iran. I was sent to Bandar-e Mahshahr in Iran’s Khuzestan province to negotiate their release.