Trump promised to end the wars in Ukraine and Gaza, yet here we are – months later – and seemingly no real progress has been made towards peace in either regions. In the meantime, Trump and co were also seeking deals across the Middle East, including a new nuclear deal with Iran. How did that go? It ended in full scale War! Is the Art of the Deal dead? Is Trump a fool? Or is he more of a master negotiator than is immediately apparent? Did he actually manipulate the Iranians in a way that Biden never could have?

To discuss this – and the intricate relationship between human psychology and the politics of negotiations – Jason was joined on June 10 by Ken Dekleva. A former senior US Dept of State physician-diplomat, CEO of Blackwood Advisory Solutions LLC, and Author of The Russian Diplomat’s Wife.

Ken and Jason discuss the role of human psychology in Trump’s negotiations involving Ukraine, Russia, and Iran. Plus: they unpack the influence of Steve Witkoff within Trump’s inner circle, the complexities of negotiations in the Middle East – and whether Team Trump is likely to get any sort of deal with powers like Iran who wish to appear uncompromising. Listening to this discussion post Israeli Attack on Iran is actually super interesting as it shows the interplay btw negotiations and war in that region.

And as they Order the Disorder, they touch on the future of U.S.-China relations in the context of AI and global power dynamics, and the need for a strategic approach to negotiations.

Producer: George McDonagh

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Show Notes Links:

Get Ken’s Book, The Russian Diplomat’s Wife - https://www.thecipherbrief.com/book-review/i-spy-a-love-story

Listen to our previous episode with Ken - https://pod.link/1706818264/episode/94c9f3ec23902d3f606bffb43dc39928 

Watch Does NATO Have A Future? https://www.youtube.com/watch?v=0ouF6cVUJjY 

Read profile of Steve Witkoff https://www.theatlantic.com/politics/archive/2025/05/steve-witkoff-putin-russia-ukraine-diplomat/682805/ 

Read Arthur Snells Substack on the Ukraine drone attack - https://arthursnell.substack.com/p/operation-spiders-web-opening-pandoras?utm_source=substack&utm_campaign=post_embed&utm_medium=web 

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