To free Israeli hostages Iran must feel the pain, ex-intel officer says

An ultimatum by US President Donald Trump to Hamas is doomed to fail unless Tehran faces a genuine threat and consequences for backing the group, Michael Pregent, a former US Intelligence officer and military adviser told Eye for Iran podcast.

“Tehran needs to feel under threat, and they need to feel pain,” said Pregent.

"What kind of pressure can the Trump administration put on Iran to get those hostages released? They just simply have to say, you are going to be held accountable for every hostage that's killed or delay in the release of every hostage."

The United States, Pregent said, should exert economic pressure on Iran, discourage Iraqi cooperation with Tehran and more directly confront armed affiliates in the region such as the Houthis in Yemen, Lebanese Hezbollah and Hamas itself.

"If the regime told Hamas to release, they would release," Pregent said, referring to Iranian authorities and Israeli hostages Hamas seized in an Oct. 7, 2023 attack.

Trump on Monday warned of dire consequence if all the remaining hostages are not released on Saturday.

“As far as I’m concerned, if all of the hostages aren’t returned by Saturday at 12 o’clock – I think it’s an appropriate time – I would say, cancel it (ceasefire) and all bets are off and let hell break out,” the president told reporters in the White House.

Trump’s comments represent one of the most direct threats aimed at the Iran-backed group by any Western leader. He also says he seeks to seize and control Gaza, the coastal enclave that has been run by Hamas.

The Islamic Republic provides material, financial and ideological support to its Palestinian ally. According to a 2020 US state department report, Iran provides about $100 million annually to Palestinian militant groups, including Hamas.

Qatar's role

Pregent, who served under former director of the Central Intelligence Agency, General David Petraeus in Iraq, describes Trump as a tough and effective leader.

The Republican President understands the Middle East, Pregent said, but added that some members of the administration are too close to Qatar.

“That funding either silences a critic or results in praise for what Qatar is doing. We hear these things like Qatar is doing God's work,” said Pregent. “When it comes to Witkoff, we know that they bought a property in New York for $623 million. That's in The New York Times. I'm not saying that he's bought and paid for.”

Steve Witkoff, once a prominent real estate investor, is the US Special Envoy to the Middle East, who played a pivotal role in brokering a major ceasefire and hostage exchange agreement between Israel and Hamas.

A New York Times report alleges that Witkoff was involved with two sovereign wealth funds when he bought and sold a Manhattan hotel in 2018 prior to working in government. The Qatar investment authority purchased the hotel for $623 million helping to secure a buyout for Witkoff and his partners.

The most senior leader of Hamas outside of Gaza was living in Qatar up until recently, but the political office of Hamas in Doha is now permanently closed, Qatar’s foreign ministry spokesperson told various Western-media outlets.

Qatar, a tiny island in the Persian Gulf, has become the world’s lead hostage-negotiator. The small energy-rich state, with the help of Egypt, has been working with the US and Israel on a Israel-Gaza ceasefire for much of the conflict.

In 2023, just before October 7, Doha brokered a deal between Washington and Tehran that saw the release of US hostages inside Iran in exchange for the release of 6 billion to Tehran in frozen assets.

“You cannot succeed if you continue to play into the hands of the arsonist playing firefighter, you know, in the role of Qatar. If you really want to get a release, Tehran needs to be involved,” said Pregent.

Pregent said while Iran influences Hamas, Qatar influences the US.

“What I'm saying is it’s pretty hard to criticize Qatar when they buy you out of a financial situation that you are in. That's what I'm talking about with this influence,” added Pregent.

If Doha continues to lead negotiations, and Tehran doesn't face consequences for its support of Hamas, Pregent insisted, there can be no progress to end the conflict.

"If that doesn't happen, then nothing."