This week we talk about Khamenei, Trump, and Netanyahu.

We also discuss Venezuela, Cuba, and cartels.

Recommended Book: Plagues upon the Earth by Kyle Harper

Transcript

Ali Hosseini Khamenei was an opposition politician in the lead-up to the Iranian Revolution that, in 1979, resulted in the overthrow of the Shah—the country’s generally Western government-approved royal leader—and installed the Islamic Republic, an extremely conservative Shia government that took the reins of Iran following the Shah’s toppling.

Khamenei was Iran’s third president, post-Shah, and he was president during the Iran-Iraq War from 1981-1989, during which the Supreme Leader of Iran, the head of the country, Ruhollah Khomeini sought the overthrow of then Iraqi leader Saddam Hussein. Khomeini died the same year the war ended, 1989, and Khamenei was elected to the role of Supreme Leader by the country’s Assembly of Experts, which is responsible for determining such roles.

The new Supreme Leader Khamenei was reportedly initially concerned that he wasn’t suitable for the role, as his predecessor was a Grand Ayatollah of the faith, while he was just a mid-rank cleric, but the constitution of Iran was amended so that higher religious office was no longer required in a Supreme Leader, and in short order Khamenei moved to expound upon Iran’s non-military nuclear program, to expand the use and reach of the Islamic Revolutionary Guard Corps, in-country and throughout the region, and he doubled-down on supporting regional proxies like Hezbollah in Lebanon, the Houthis in Yemen, and Hamas in Gaza, incorporating them into the so-called Axis of Resistance that stands against Western interests in the region—the specifics of which have varied over the decades, but which currently includes the aforementioned Hezbollah and Houthis, alongside smaller groups in neighboring countries, like Shiite militias in Bahrain, and forces that operate in other regional spheres of influence, like North Korea, Venezuela, and at times, portions of the Syrian government.

Khamenei also reinforced the Iranian government’s power over pretty much every aspect of state function, disempowering political opponents, cracking down on anyone who doesn’t toe a very conservative extremist line—women showing their hair in public, for instance, have been black-bagged and sometimes killed while in custody—and thoroughly entangled the functions of state with the Iranian military, consolidating essentially all power under his office, Supreme Leader, while violently cracking down on anyone who opposed his doing whatever he pleased, as was the case with a wave of late-2025, early 2026 protests across the country, during which Iranian government forces massacred civilians, killing somewhere between 3,000 and 35,000 people, depending on whose numbers you believe.

What I’d like to talk about today is a new war with Iran, kicked off by attacks on the country from Israel and the United States that led with the killing of Khamenei and a bunch of his higher-up officers, how this conflict is spreading across the region and concerns about that spreading, and what might happen next.

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On February 28, 2026, the US and Israel launched a wave of joint air attacks against Iran, hitting mostly military and government sites across the country. One of the targets was Khamenei’s compound, and his presence there, above-ground, which was unusual for him, as he spent most of his time deep underground in difficult-to-hit bunkers, alongside a bunch of government and military higher-ups, may have been the rationale for launching all of these attacks on that day, as the attackers were able to kill him and five other top-level Iranian leaders, who he was meeting with, at the same time.

This wave of attacks followed the largest military buildup of US forces in the Middle East since the invasion of Iraq back in 2003, and while military and government targets were prioritized, that initial wave also demolished a lot of civilian structures, including schools, hospitals, and the Grand Bazaar in Tehran, leading to a whole lot of civilian casualties and fatalities, as well.

In response, Iran launched hundreds of ballistic missiles and drones at Israel, and at US bases throughout the region—these bases located in otherwise uninvolved countries, including Qatar, Bahrain, the UAE, Kuwait, Iraq, Jordan, and Saudi Arabia. Iranian missiles and drones also hit non-military targets, and in some cases maybe accidentally hit civilian infrastructure, in Azerbaijan, and Oman, alongside a British military base on the island of Cyprus.

The Iranian president apologized in early March for his country’s lashing out at pretty much everyone, saying that there were miscommunications within the Iranian military, and that Iran wouldn’t hit anyone else, including countries with US bases, so long as US attacks didn’t originate from those bases.

Despite that apology, though, Iranian missiles and drones continued to land in many of those neighboring countries following his remarks, raising questions about communications and control within the now-decapitated Iranian military.

This new conflict follows long-simmering tensions between Iran and Israel—the former of which has said it will someday wipe the latter from the face of the Earth, considering its existence an abomination—and long-simmering tensions related to Iran’s nuclear program, which the government has continuously said is just for civilian, energy purposes, but which pretty much everyone suspects, with a fair bit of evidence, is, in parallel, also a weapons program.

Iran’s influence throughout the region has been truncated in recent years, due to a sequence of successes by the Israeli military and intelligence services, which allowed them to hobble or nearly wipe out traditional Iranian proxy forces like Hamas, Hezbollah, and the Houthis, which have collectively surrounded and menaced Israel for decades.

Those menacing forces more or less handled, Israel has become more aggressive in its confrontations with Iran, exchanging large air attacks several times over the past handful of years, and the US under Trump’s second term continues to see Iran as the main opposition to their efforts to build a US-aligned counterbalance against Russian and Chinese influence in the Middle East, with Israel, Saudi Arabia, and increasingly entities like Qatar and the UAE playing ball with the West, while Iran and its allies stand firm against the West.

Trump has regularly threatened to act in Iran, usually waiting for the Iranian government to do something really bad, like that recent massacre of civilians following those large anti-government protests in late-2025, early 2026, and that to some degree has served as justification for the massing of US military assets in the region, leading up to this attack.

Now that the attack has launched, a new war triggered, the question is how big it will get and how long it will last.

For the moment, it looks like Iran’s government and military is very much on the back foot, a lot of their assets taken out in that initial wave, and they’re still scrambling to put someone in charge to replace Khamenei and those other higher-ups who were assassinated at the outset of this war—that’ll likely change soon, maybe even before this episode goes live. But whomever takes the reins will have quite the task ahead of them, probably—according to many analysts, at least—aiming to just hold out until the US runs out of ammunition, which is expected to happen within a week or so, at which point Iran can launch surgical attacks, aiming to make this war too expensive, in terms of money and US lives, for the Trump administration to continue investing in, as money and lives are especially expensive in an election year, which 2026 is. So the idea is to grind the US down until it makes more political sense for Trump to just declare victory and leave, rather than allowing this to become a Vietnam or Afghanistan situation for his administration.

It’s also generally expected that when the US pulls out, Israel probably will too, as they’ve already made their point, tallied a bunch of victories, and set Iran back in a lot of ways; they could walk away whenever they like and say they won. And Iran would probably be incentivized to, at that point, avoid doing anything that would lead to more punishment, though they would almost certainly immediately begin rebuilding the same exact centralized, militarized infrastructure that was damaged, the only difference being they would have someone else on top, as the Supreme Leader. Relations could be even worse moving forward, but it would probably be at least a few years before Iran could do anything too significant to their regional enemies, which I guess if you’re Israel does, in fact, represent a win.

But considering the unlikelihood of permanent change in Iran, the big question here, in the minds of many, is what this war, this attack, is even for.

For Israel, the main purpose of any attack against Iran is to weaken or destroy an enemy that has made no secret about wanting to weaken and destroy them. For the US, though, and the Trump administration more specifically, the point of all this isn’t as clear.

Some contend that this is another effort to steal attention and headlines from the increasingly horrifying revelations coming out of the investigation into the Epstein files, which seem to indicate Trump himself was involved in all sorts of horrible, pedophilic sexual assault activities with the late human-trafficker.

Some suspect that the apparent victory in grabbing former Venezuelan president Maduro from his own country and whisking him away to the US without suffering any US casualties has embolden...