Jesse Kline: Yahya Sinwar’s luck finally runs out

Few life stories show how small decisions and twists of fate can have massive historical consequences as that of Yahya Sinwar, the Hamas leader and mastermind of the October 7 massacre who was killed in Gaza on Wednesday.

A member of Hamas since its inception in 1987, Sinwar was convicted of brutally murdering four Palestinians suspected of collaborating with Israel and sentenced to four consecutive life terms in 1989. In prison, Sinwar learned Hebrew and used the time to read books and Israeli media in order to better understand his enemy.

By all rights, he should have died in prison, either from old age or cancer, but that is not what fate had in store for him.

In 2004, Sinwar fell ill, and it was the prison’s dentist, Yuval Bitton, who realized that something was wrong with his brain. Sinwar was rushed to hospital where Israeli doctors removed a brain tumour that would have been fatal if left untreated. According to Bitton, Sinwar had said “he owed me his life,” but it was a debt that would never be repaid (quite the opposite, in fact).

During Sinwar’s 23 years behind bars, much changed in the outside world. Israel withdrew from Gaza in 2005. In January 2006, Hamas won a surprise victory in the Palestinian legislative elections and cemented its hold on power in the Strip in a bloody coup the following year.

But it was a small cross-border raid on June 25, 2006 that changed the course of Sinwar’s life. In an assault that bore an eerie resemblance to October 7, though on a much smaller scale, at the crack of dawn, a squad of Hamas terrorists invaded Israel through a tunnel dug under the Kerem Shalom border crossing and began attacking military targets. Two soldiers were killed and another, Gilad Shalit, was kidnapped.

Shalit languished in Hamas captivity for five years before a deal was struck to set him free in exchange for 1,027 Palestinian prisoners, including 280 who were serving life sentences. Among them was one Yahya Sinwar.

Immediately following his release, Sinwar admitted he had learned a valuable lesson from the whole affair — namely, that kidnapping Israelis was a surefire way to get Israel to set his fellow terrorists free. “The issue of prisoners can only be resolved in this way,” Sinwar said in 2011. “For the prisoner, capturing an Israeli soldier is the best news in the universe, because he knows that a glimmer of hope has been opened for him.”

Sinwar once again joined Hamas and quickly moved up the ranks, becoming its leader in Gaza in 2017. It was in this position that he began planning the October 7 massacre as far back as 2021, as detailed in a series of newspaper reports this week, based on documents the Israel Defence Forces seized from Gaza.

According to documents obtained by the Washington Post, Hamas considered numerous options for attacking Israel, which ranged from a 9/11-style attack on Tel Aviv skyscrapers, to using Israel’s rail network to transport fighters and bombs into the heart of major cities, to terrorists riding on horse-drawn chariots.

Minutes of high-level Hamas meetings seen by the New York Times show that Sinwar and his inner circle spent years planning the assault, referred to as “the big project,” which included a “large and convincing disguise and deception process” intended to lull the Israelis into a false sense of security by giving the impression that Hamas was not interested in a major confrontation with Israel.

Although Sinwar’s battle plans were ready in the summer of 2022 — plans that were intercepted by the Israelis but discounted as being unrealistic — he held off for over a year to give him time to petition the Iranians to provide Hamas with more military and financial resources and persuade Iran and Hezbollah to join the fight against Israel once “the big project” was put into action.

The attack was ultimately launched on Oct. 7, 2023, when some 6,000 terrorists stormed across the border, raping and murdering 1,200 people, mostly civilians, and taking over 250 hostages to barter for the release of more terrorists. Among the dead was Tamir Adar, the nephew of Yuval Bitton, the Israeli dentist who saved Sinwar’s life.

For a year following the October 7 attack, Sinwar managed to evade the Israelis by hiding in Hamas’s extensive tunnel network, communicating using a crude yet complex system of hand-delivered coded messages and reportedly dressing in drag to move around above ground undetected.

His ultimate demise came about through sheer happenstance. On Wednesday, Israeli soldiers found themselves in a firefight with a group of terrorists holed up on the ground floor of a building in Rafah. An Israeli tank fired at the building, causing it to collapse. Afterwards, troops found a body that closely resembled Sinwar — an identification that Israeli officials were able to confirm on Thursday.

Graphic images posted to social media show a body that looks like a zombie that died after a large spike was driven through its brain. But Sinwar was not a villain conjured up in a Hollywood writers room; he was a real life monster who built a career around his callous disregard for human lives and human suffering — both Israeli and Palestinian. He could not have met a more fitting end.

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