How October 7th Became the Middle East's Pearl Harbor

On the big list of historical military miscalculations, there are some that are destined to always come near the top.

Vladimir Putin's decision to only plan for a short war against Ukraine, for example, or Imperial Japan's decision to bomb Pearl Harbor, a decision that dragged the United States into the Second World War, and spoiler alert here, it didn't end well for Japan.

Well, from our historical vantage point of 2026, it now seems like the attacks of October 7, 2023 are fated to join that list.

What Yaha Sinwa set in motion that morning has, over the past two and a half years, destroyed an entire alliance stretching from Beirut to Baghdad to Sana'a, and very well may end up taking the Islamic Republic down with it. This is the story of how Hamas' biggest attack wound up becoming the Pearl Harbor of the Middle East.

The Big Project In the spring of 2022, Yaha Sinwa sat down to begin writing a memo.

It wasn't the kind of document that typically changes the course of history, handwritten, deeply personal, more manifesto than military order. But when Israeli forces recovered it alongside other documents from various planning sessions held in Gaza since the May 2021 war, the scope of what Hamas had been building was made clear for all to see.

The codename was The Big Project, and its ambitions went far beyond anything the group had ever attempted before.

To understand what Sinwa was building toward, you have to understand what Hamas actually wanted from all of this. Gaza has long been a staging ground for something larger, the eventual replacement of the Israeli state, with an Islamic-Palestinian entity from the Jordan River to the Mediterranean.

At a 2021 conference dedicated to governing Israel after its destruction, Sinwa declared that victory is nigh, and later called for a roaring flood to destroy the state.

IRGC commander Hossein Salami argued the following year that Palestinian factions were now strong enough to transition from rockets and missiles to deploying ground forces that would liberate Palestine step by step.

October 7th was supposed to be the opening act of that next phase, though hindsight does suggest that their timeline was accelerated by the looming threat of Saudi-Israeli normalizations. Now, Riyadh would have been the first Arab state to recognize Israel.

Far from it. Jordan had done so all the way back in 1994, and several Gulf states had joined Amman by recognizing the state of Israel as part of President Trump's Abraham Accords back in 2020.

That slow trickle of more countries beginning to move away from Hamas's maximalist goals and towards a recognition of Israel as part of what they hoped would be a two-state solution scared the sh** out of Hamas leaders.

In terms of what might come next, Saudi Arabia was by far their biggest concern. While the likes of the UAE's foreign minister shaking hands at the White House with Donald Trump and Benjamin Netanyahu wasn't a welcome sight for them, Riyadh was still in a league of their own.

Hamas believed if they lost them, it would be game over in terms of ever being able to fully expel Israel from the area.

This fear played a big role in expediting their plans to launch the October 7th attack. They believed, not incorrectly, that starting another major Israeli-Palestinian conflict would make any proposed normalization between Saudi Arabia and Israel effectively dead on arrival.

We'll save you all the details of what exactly happened during the attack, as we're sure you've heard about it extensively, but suffice it to say, it shook Israel to its core.

Somewhere between 1,500 and 3,000 fighters breached one of the most surveilled borders on Earth, killing over 1,200 Israelis in a single day. But the operation that Hamas actually carried out wasn't exactly what Sinwar had planned for.

The operational blueprint drew heavily from a 2012 Hezbollah plan that the IDF had discovered, which envisioned elite units infiltrating across the border into Israel, seizing communities, fortifying positions, and using Israeli civilians as hostages inside Israel in preparation for the inevitable counterattack that was to come.

Hamas's plan was basically a copy-paste version of this. Breached the border, seized towns, and buckled down there, creating defended positions on Israeli soil that would have been extraordinarily difficult to dislodge. Obviously, that's not what happened.

Sinwar kept the full operational plan compartmentalized, with most fighters understanding only their immediate objectives.

When the breach succeeded far beyond what the rank-and-file had expected, and secondary waves of Hamas members and Palestinian Islamic Jihad fighters began to flood through the now-open wall into Israel, the operation lost coherence and structure almost immediately.

Fighters who didn't know they were supposed to hold territory inside Israel defaulted to just grabbing people and dragging them back to Gaza.

Now, that's not to say that hostage-taking has ever gone particularly well in terms of leverage over Israel. When Palestinian militants took Israeli athletes hostage at the 1972 Munich Olympics, then-Prime Minister Gold Amer refused outright to negotiate, declaring that if Israel gave in, none of its citizens would ever be safe again.

She then authorized a years-long assassination campaign to hunt down everyone who was involved, an operation that was literally titled Wrath of God.

So, the historical track record wasn't exactly encouraging, but Hamas pressed ahead regardless. They figured that there would, of course, be some Israeli response into Gaza, but combined with everything else that was going to be going on, they welcomed it, as they thought they'd be trapping the limited IDF personnel in unfamiliar territory.

The failures on the ground were only a part of Omen Rondo.

Sinwar's entire strategy rested on an incredibly complicated, multi-front war that was supposed to overwhelm Israel from every direction simultaneously. Hezbollah opening a second front from the north, the Houthis striking from Yemen, Iraqi Shiite militias targeting American bases, and uprisings among Israeli Arabs.

Iran's role in the broader planning is difficult to pin down definitively, but whatever Tehran knew about the timing, the wider axis was not ready when the fighters crossed the border.

The ring of fire never materialized. realized, because the same compartmentalization that made the breach possible is exactly what prevented the broader war from kicking off.

The Domino Chain Every recent war that Israel was involved in before October 2023, especially as it pertains to Palestinian organizations, ended in a matter of weeks, whether because Israel had achieved its limited objectives or because the international pressure made continuation politically untenable.

It became a predictable facet around which Hamas built an entire military doctrine, absorbed the initial Israeli assault, conducted a delaying operation, and emerged from the rubble with your leadership more or less intact.

So it wasn't exactly a surprise for any of them that Jerusalem was going to hit back after their attack, even if their hostage strategy had been more effective. The price they would pay, however, was just a bit higher than they had planned for.

The entire defense theory behind Iran's regional architecture rested on the assumption that any serious move against one member would trigger retaliation from the others.

It wasn't quite a NATO Article 5 doctrine, but the mutual defense was there. At least it was in theory. You see, the restraint that we saw from its members over the last few years wasn't because of any ideological attachment to keeping the peace in the region, but rather a display of how the axis of resistance was designed to function.

Unlike with NATO, where an attack on one is supposed to be registered as an attack on all, Iran's alliance was set up in a far more one-way direction. Tehran may have been generous to its proxies in terms of both military hardware as well as funding, but the reason for funding those groups in the first place was unmistakably clear.

Protecting Iran, not the other way around.

Remember, Hezbollah was Iran's most valuable asset. Their missile stockpile was the guarantee, that neither the US nor Israel would dare to make a regime-change-style move against them. This made Hezbollah into the more or less crown jewel of the whole strategy, which meant that putting them at risk would inherently put Tehran at risk as well.

Had Tehran really wanted Hezbollah to begin an all-out campaign against Israel, they likely could have achieved some serious damage earlier on. But in doing so, they would be cashing in their best defense, and in all likelihood, be kicking off a full-scale war with Jerusalem as a result.

The result was a low-level campaign that could be offered as a face-saving measure, but had limited impact on Israel.

Hezbollah did launch cross-border skirmishers, and northern Israeli Moshavs had to evacuate. But it wasn't exactly the nation-destroying rocket barrage that had been expected. In September of 2024, Israel decided to end the threat on its own terms, after making significant progress against Hamas in the Gaza War.

It started with a now infamous pager operation, a covert operation that took out roughly 1,500 fighters in a single day. This left the organization crippled in terms of command and control. As one analyst put it, the people running Hezbollah after that were the guys who were determined not to be deserving enough of a pager before the attack.

Israel's subsequent air and ground campaign, which followed Tor through their remaining personnel. And so on. stockpiles alike, ultimately cutting their precision rocket stockpile by about a half and culminating in an airstrike that killed their longtime leader, Hassan Nasrallah.

The ceasefire they agreed to later that year would have been absolutely unthinkable just a few months prior.

In short, Hamas had calculated, or perhaps hoped, that their incursion into Israel would bring Iran's other proxies into the fight. Instead, the most powerful proxy held back, allowing Jerusalem to later destroy it at its leisure. And if all of that wasn't enough, 2024 had one final surprise.

After over a decade of barely hanging onto power through a brutal civil war, Bashar al-Assad's regime in Syria finally, and rather unexpectedly, collapsed.

The autocrat fled to Moscow, and the new government set up in Damascus made it absolutely clear from the outset that the days of permitting Iran to use their land to smuggle weapons to Hezbollah were over. Had events frozen at this point, it would have been enough to classify October 7th as one of the great backfires of all time.

But of course, things didn't end at this point, and they would soon get far worse for the axis of resistance. If the destruction of the axis through 2024 had exposed the hollowness of Iran's deterrence, it looked like a warm-up compared to what was to come in 2025 and early 2026.

By the time President Trump took office in early 2025, the axis was already a shell of its former self.

But the change in who was in the Oval Office fundamentally upended the rules of the game in ways that, looking back on it, we don't think anyone fully realized.

Joe Biden was quite supportive of Israel throughout his time in office, something which may have cost the Democratic Party votes among parts of its base, but he also wasn't exactly going to be launching the likes of Operation Epic Fury either.

Trump is a long-time Iran hawk, having carried out the assassination of Islamic Revolutionary Guard Corps General Qasim Soleimani and famously withdrawn from the original nuclear deal reached with Iran under President Obama's tenure.

Iran's economy had been deteriorating under the weight of international sanctions for years, but by 2025, things were inching into disaster territory. Their currency was in freefall, and economic activity throughout the country was beginning to grind to a halt. This presented an entirely new issue for the axis.

You can't rebuild a crippled alliance if the top dog itself is bankrupt. All of this came on top of the 2024 back and forth between Israel and Iran, which had revealed that Iranian airspace was far more permeable than either side had assumed.

Israeli strikes that followed, Nasrullah's assassination, had systematically dismantled Iran's S-300 air defense batteries, leaving them more exposed than they'd been at any point since the Iran-Iraq war.

The window, left open from this operation, and further expanded during Operation Rising Lion in the summer of 2025, was not indefinite though, and signs were emerging that Tehran was already moving to rearm its proxy forces.

Trump eventually called off hostilities following Operation Midnight Hammer, which struck several of Iran's nuclear facilities, insisting that diplomacy be given a chance. Now, this wasn't exactly pacifism, it was far more along the lines of surrender or we'll bomb you, which has consisted of much of his foreign policy lately.

But this was also where Iran's mistakes really started to take a toll. Rather than treating the strikes as a wake-up call, the regime processed the experience through what one analyst called a survivalist lens. If something that can kill you doesn't destroy you, it makes you stronger.

The lesson they drew was not that they were dangerously exposed, but that they could endure. The negotiations that followed made clear just how out of touch the regime was.

Tehran approached them as if they were dealing from a position of strength, demanding sweeping sanctions relief while categorically refusing to even discuss limits to their missile programs or funding for their proxy network.

Whether or not the diplomatic class in Iran thought that a military campaign against them on this scale would actually happen is something that analysts and historians alike will debate for years to come. Either way, it's exactly what they got. Out of options.

The question now, then, is whether the Axis has fully absorbed what historic mistake the last two and a half years were. Hamas co-founder Musa Abumarjuk snapped during a television interview when pressed on whether October 7th had served any purpose.

No rational person, he said, would believe that an operation involving roughly 1,000 fighters was ever going to achieve the liberation of Palestine.

Clearly, a bit of a gold shift from the earlier stages. Our Pearl Harbor comparison, in all honesty, fails not because it's too harsh, but because it's too narrow. Japan badly miscalculated how the United States would respond to the attack, and underestimated how much of the Pacific fleet would still be left intact after their bombing raids had finished.

This ultimately led to the destruction of their empire. Sinwar's miscalculations, as well as those shared more broadly throughout the Axis, destroyed far more than just Gaza. They destroyed an entire regional architecture that extended from Beirut to Baghdad to Sana'a.

In particular, the last two years or so show that the Axis was built on a structural vulnerability that its architects never adequately addressed. By centralizing so much focus on protecting Iran in particular, the group was uniquely vulnerable to being picked off one at a time.

Hezbollah could only offer minimal assistance to Hamas, because if they went at it too hard, Israel would wipe them out, leaving Tehran as a sitting duck.

Likewise, when Israel did turn its attention to Hezbollah, Iran's only options were to either start a regional war, one that it would almost certainly lose, especially given the damage that it had already done to its proxy forces by that point, or to carry out a few face-saving missile launches and try to call it a day.

Now, if you're wondering at this point what the better option was for Tehran, well, that's going to be up to you. But the key point here...

Thank you. is just how bad all their options were by choosing the latter to run effectively signed the death warrant of the network that it had spent decades building leaving them completely exposed to what was to come at the end of february this year and with that thank you for watching