President Trump set an eight o’clock Eastern time deadline Monday evening for Iran to come to terms on reopening the Strait of Hormuz, threatening to simultaneously destroy every bridge and power plant in Iran within four hours if no agreement was reached, while simultaneously expressing deep frustration with NATO allies who have declined to participate in the campaign despite their far greater dependence on Persian Gulf energy flows than the United States.
Retired Lieutenant Colonel Tony Shaffer, president of Project Sentinel and the London Center for Policy Research and author of Operation Dark Heart, joined Dan Proft on Chicago’s Morning Answer to assess what Trump is actually signaling and what comes next.
Shaffer said the most important context for understanding Trump’s deadline and his threats against Iranian infrastructure is not the Iranians but the Europeans. The United Kingdom imports roughly eighty percent of its liquefied natural gas from Oman, a supply that has been disrupted. European nations depend heavily on imports from Africa, whose fertilizer supply chains run through the Middle East. These countries are objectively more exposed to the economic consequences of a closed strait than the United States, and yet they have declined to contribute meaningfully to the effort to reopen it. Shaffer said people he has spoken to in the administration told him that even a statement of political support from NATO allies, even without any immediate military contribution, would have changed the conversation. The failure to provide even that has produced the visible frustration Trump expressed publicly, noting that when he asked the United Kingdom for help the British response was that they would rather wait until America won, to which Trump replied that he would not need help after winning. NATO Secretary General Mark Rutte was scheduled to be in Washington Tuesday, Shaffer said, and the timing of the threats is not coincidental.
On the substance of the deadline itself, Shaffer said he does not believe Trump will attempt to destroy every power plant and bridge in Iran simultaneously even if no agreement materializes by eight o’clock. He said the pattern is more consistent with what happened with the bridge strike a few days earlier, when Trump described receiving word during negotiations that the Iranians were breaking the deal, giving the order to strike the largest bridge in Iran, and watching the negotiations shift within minutes. He expects a similar approach this time, with strikes on a handful of carefully selected targets rather than a comprehensive campaign against civilian infrastructure, designed to demonstrate credibility and focus minds in Tehran and in European capitals simultaneously.
On the legal question some commentators have raised about strikes against Iranian civilian infrastructure, Shaffer dismissed the war crimes framing directly, noting that the first Gulf War saw the United States destroy Saddam Hussein’s entire power grid and most of his transportation network in the opening days of the conflict. When a nation is engaged in armed hostilities, infrastructure with dual civilian and military utility is a lawful target under the laws of war. He attributed the persistence of the war crimes narrative in American media at least partly to Iranian influence operations, noting that a portion of the funds the Obama administration transferred to Iran through the nuclear deal has reportedly been recycled into lobbying and influence activities inside the United States.
Shaffer addressed the opaque state of Iranian leadership, noting that the current Ayatollah was reportedly receiving treatment at a facility in Qom for a condition preventing him from speaking, and that negotiating teams on the Iranian side can change rapidly as the military campaign continues removing figures from the chain of command. He said this makes it genuinely difficult to know who has the authority to make and keep any agreement, and that the IRGC in particular appears to be operating on something close to automatic, continuing to carry out its core function of terror and disruption regardless of what political figures nominally above it are saying to intermediaries.
Fox News reporter Trey Yingst reported this week that Trump told him the United States sent weapons to Iranian protesters through the Kurds, and that Trump suspects the Kurds kept many of the guns intended for the Iranian opposition. Shaffer said he views that disclosure as primarily a negotiating position and psychological pressure tactic rather than a literal account of a reliable weapons pipeline, noting that the Kurds have their own distinct interests that do not fully align with American objectives in Iran and that invoking the Kurds reliably produces anxiety in Turkey. He said he is not fully comfortable with the Kurdish arms channel as described and believes the statement’s primary purpose is to create uncertainty in Tehran about what the United States may do next.
He cited retired General Frank McKenzie, former CENTCOM commander, who said on Face the Nation that if he had been presented thirty days ago with a scenario describing the current state of the campaign he would have rejected it as implausibly optimistic, a striking assessment from a senior officer with direct knowledge of the planning involved. Shaffer said the campaign has struck over thirteen thousand targets with minimal American casualties and has objectively degraded Iran’s military capacity in ways that will have strategic consequences for years. He acknowledged that not every stated objective has been achieved on the hoped-for timeline and that Trump was probably more optimistic about the schedule than the operational reality warranted, but he rejected the characterization advanced by critics that the United States is losing. His view is that the campaign needs to resolve the strait before the economic pain feeding into elevated gas prices and broader market anxiety creates political damage heading into the November midterms, and that the combination of continued military pressure, European incentivization, and Gulf state coalition building is the most plausible path to that outcome.