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Uncomfortable Conversations with Josh Szeps

BLOCKADE COUNTDOWN: What's the End Game?

Uncomfortable Conversations with Josh Szeps

Josh Szeps

Society & Culture, Education, Comedy Interviews, Comedy, Self-improvement

4.5905 Ratings

🗓️ 16 April 2026

⏱️ 47 minutes

🧾️ Download transcript

Summary

What is the end game in Iran? What is the blockade achieving? What cards does Iran still hold? Last week, the end was in sight with a two-week ceasefire. Then talks in Pakistan between the US vice president and the Iranians went nowhere, and Trump suddenly imposed a blockade. Since Monday, U.S. forces say they’ve now completely halted all economic trade leaving Iran’s ports. Iran say they’ll retaliate if the blockade continues. Where does the escalation lead? Does Trump have anything left up his sleeve? What exit ramps are there for either side? Steven Simon served in the US State Department, where he specialised in the Middle East and counter-terrorism on President Clinton’s National Security Council. President Obama brought him back into the White House to serve as the NSC’s Senior Director for the Middle East and North Africa. He’s a leading world expert on Iran and co-wrote a book in 2011 called “The sixth crisis: Iran, Israel, America and the rumors of war.” His most recent book is “Grand Delusion: The Rise and Fall of American Ambition in the Middle East.” Steven joined Josh to explain the logic (or illogic) of Trump’s blockade... and what thirty years of shaping US policy in the Middle East has taught him about how this conflict is likely to end.

Transcript

Click on a timestamp to play from that location

0:00.0

What left to my mind when the blockade was announced this,

0:05.0

then it would have been the logical place to begin the war.

0:11.7

Gahy, humans.

0:13.4

Welcome to the safe space for dangerous ideas.

0:17.2

Well, we all have many dangerous and uncomfortable questions about the end game of the blockade and the war in Iran.

0:25.3

Last week, it seemed like the end may have been in sight with a two-week ceasefire.

0:31.3

Then talks in Pakistan between the US Vice President and the Iranians went nowhere,

0:36.0

and President Trump suddenly imposed

0:39.0

a blockade of the Straits of Hormuz. That went into effect on Monday, and US forces say that

0:46.0

they've now completely halted all economic trade going into and out of Iran by sea.

0:53.2

Iran's armed forces say they'll retaliate if the blockade

0:56.5

continues. Where does the escalation lead? Does President Trump have anything left up his sleeve?

1:03.4

What exit ramps are there for either side? I wanted answers to all these questions and more.

1:09.6

And the perfect man to offer them is

1:11.5

Stephen Simon, who served in the US State Department. He specialized in Middle East and

1:16.9

counterterrorism policy in President Clinton's National Security Council. President

1:21.8

Obama then brought him back into the White House to serve as the NSC's senior director

1:26.6

for the Middle East and North Africa,

1:28.7

so he has some pedigree.

1:31.0

He's a leading world expert on Iran.

1:33.2

In 2011, he co-wrote a book called The Sixth Crisis, Iran, Israel, America and the

1:38.5

Rumors of War.

...

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