Decades before he orchestrated the October 7 attacks by Hamas on Israel, Yahya Sinwar was jailed by an Israeli military tribunal for multiple murders. His response: to study Hebrew.
“(Vladimir) Jabotinsky and (Menachem) Begin and (Yitzhak) Rabin — he read all the books that came out about prominent Israeli figures,” said Micha Kobi, who interrogated Sinwar for the Shin Bet intelligence service. “He learned us from the bottom all the way to the top.”
Then, fifteen years into his sentence, he deployed his pitch perfect Hebrew in an Israeli television interview. Rather than war, he urged the Israeli public to support a hudna, or truce, with the Hamas militant group.
“We understand that Israel sits on 200 nuclear warheads and it has the most advanced . . . air force in the region. We know that we don’t have the ability to dismantle Israel,” said the Palestinian, wearing a crimson jumper.
Yet for all that, Sinwar, 61, is today Israel’s most wanted man; Benjamin Netanyahu, Israel’s prime minister, refers to him as a “dead man walking”. The leader of the Hamas militant group in Gaza is deemed the single figure most responsible for the surprise attack on October 7 that killed more than 1,400 Israelis, including women, children and the elderly.
His elimination is the primary objective of the escalating Israeli campaign to “destroy” Hamas. Palestinian officials say some 9,770 people have been killed in Gaza since Israel began its retaliation for the assault, destroying large areas of the Hamas-controlled territory in attacks from land, air and sea.
Ahead of the Hamas incursion, Israel had close to 40 years of experience dealing with Sinwar, an intense and violent man with a wiry frame and close-cropped hair. Yet that accumulated knowledge, in recent years, only lulled Israel’s security chiefs into a false sense of complacency.
On the eve of war, Israel viewed Sinwar as a dangerous extremist who was nevertheless biddable, more concerned with solidifying Hamas rule in Gaza and extracting economic concessions than the group’s professed aim of destroying the Jewish state.
That misreading of Sinwar’s character would be the prelude to Israel’s biggest intelligence failure. To some, Sinwar had managed the ultimate deception.
“We didn’t understand him at all, in an insane way. Zero,” said Michael Milstein, a former Israeli military intelligence officer and expert on Palestinian affairs.
The portrait of Sinwar given by several people who have spent time with him, stretching back decades, is of a charismatic man of few words, a quick temper and commanding presence.
Kobi recounts interrogating Sinwar back in 1989 when he confessed to a murder. It was the height of the first Palestinian intifada, or uprising, and Kobi was a Shin Bet officer pursuing members of Hamas, which was then a small Islamist militant group coming to the fore in Gaza.
Sinwar, widely known as Abu Ibrahim, had helped build Hamas’s military wing, the Qassam Brigades, from its early days. But when he was detained in the late 1980s, it was for his special role within Hamas: hunting down Palestinians suspected of collaborating with Israel.
Kobi said Sinwar boasted — whether accurately or as a piece of bravado — about a punishment meted out to one suspected informer from a rival faction. Sinwar summoned the man’s brother, a Hamas member, and “made him bury his own brother alive”, handing him a spoon to finish the job. “He made the brother pour and pour and pour. That’s Yahya Sinwar,” said Kobi.
Sinwar was convicted by a secret Israeli military tribunal for the murder of 12 Palestinians, including the man buried alive, according to two people familiar with the case.
He rose to become the leader of all the Hamas prisoners in Israeli jails, an influential post within the group’s hierarchy. At one point, in 2004, Israeli doctors removed an abscess lodged next to his brain, saving his life, according to Israeli authorities.
An Israeli intelligence assessment of Sinwar during his time in prison attempted to capture his character: “cruel . . . authoritative, influential, accepted by his friends and with unusual abilities of endurance, cunning and manipulative, content with little . . . keeps secrets even inside prison amongst other prisoners . . . has the ability to carry crowds.”
Raised in a slum in Khan Younis in southern Gaza, Sinwar first came on to the political scene in Gaza during the early 1980s as a “whisperer” advising Hamas’s wheelchair-bound founder, Sheikh Ahmed Yassin, who was revered within the movement.
Sinwar’s neighbour in Khan Younis was Mohammed Deif, now Hamas’s shadowy military chief. In addition to helping establish the group’s military wing, Sinwar was put in charge of its feared internal security apparatus, the Majd (Glory) Force, charged with eliminating suspected collaborators. It earned him the nickname “the butcher of Khan Younis”, which some Palestinians use to this day.
Sinwar has become an almost mythical figure for Palestinians, particularly within Gaza. “Many Palestinians feel pride, and Sinwar is very popular on the Palestinian street,” said one prominent Palestinian activist in East Jerusalem. “But moderate Palestinians understand that he has sent us back to the stone age (because of October 7 and its aftermath).”
Above all, those who know him say his rise within Hamas has relied on cultivating a reputation for ruthlessness and violence, which holds sway even among the top ranks of Hamas.
“It’s the difference between how (Hamas officials) act when they’re alone and when they’re with him,” said one non-Israeli who has years of experience dealing with Sinwar directly. “It’s fear, they’re afraid of him.”
“None of them stood up to him before he decided to execute this barbarity (on October 7). It was the perfect military operation, but the consequences will be biblical.”
Sinwar was released in 2011 after serving 22 years in an Israeli prison. He was part of an exchange in which more than 1,000 Palestinians were released for one Israeli soldier, Gilad Shalit, held by Hamas in Gaza.
By 2017, he was elected leader of the group for all of Gaza, replacing Ismail Haniyeh, who was, according to multiple people familiar with relations between the two men, “demoted upwards” to become Hamas’s political leader and then outwards to Qatar.
Now clad in a politician’s uniform of slacks and button-down shirts, Sinwar hosted foreign diplomats and held fiery rallies.
Under his leadership, Hamas calibrated its use of force — border protests, incendiary balloons, and especially rocket fire — to prod Israel into further indirect talks via Egyptian, Qatari and UN mediators.
“The rockets are their ability to hold a conversation with me,” said one senior Israeli security official earlier this year. Israel in recent years granted concessions to Gaza unthinkable just a few years ago, including more Qatari financial support and thousands of Israeli work permits.
Sinwar’s motives for his explosive turn on October 7 remain something of a riddle.
“He’s not a humble person. He has an enormous ego and sees himself as if on some sort of mission in this world,” said the non-Israeli with long experience with Sinwar. “He’s a sociopath. I don’t mean this as an insult.”
“He would think nothing of sacrificing tens of thousands of lives, and more, to achieve his goals,” he added.
In 2021, Sinwar needed a run-off ballot in Hamas’s opaque internal elections against an old rival to retain his post, which some analysts see as a potential turning point. A few months later Israel and Hamas fought an 11-day war, after which Sinwar — perched on a chair in the rubble of what had been his home — claimed “victory”.
Over the past year, one Palestinian official with close ties to Gaza travelled to the territory several times, in a bid to negotiate a wider national compact with Hamas. He met with Sinwar often, insisting there was “mutual respect”.
But on the official’s last visit to Gaza earlier this year Sinwar “disappeared completely”. “There were signals we should have read,” he said. “The camouflage of a diplomatic track for the military track.”
Yet Israel’s official assessment was that the Sinwar-led Hamas was both deterred from fighting another war and interested in a broader agreement with Israel.
According to Israeli intelligence, Hamas’s assault required at least a year of planning. Sinwar’s outwardly pragmatic facade, Israeli officials and analysts now maintain, was pure deception meant to buy time.
“We need to face it: he’s motivated by hatred, carnage, and the destruction of Israel,” Milstein, the Israeli military intelligence officer, said.
Gaza may now be facing a devastating onslaught, with Sinwar the principal target. But Israel is humbled and the fate of the region hangs in the balance. That alone may be victory enough for Sinwar. “He won’t surrender. He will die there in Gaza,” said Kobi.
