The Hamas leader who studied Israel’s psyche — and is betting his life on what he learned

Yahya Sinwar drove a strategy to exploit Israel’s willingness to trade Palestinian prisoners for hostages; Gaza leader spent two decades in prison in Israel.

After a career in the shadows, in Israeli prisons and as part of the internal security apparatus of Hamas, Yahya Sinwar rose to lead the Islamist movement in the Gaza Strip. Picture: AFP

When Hamas leader Yahya Sinwar was imprisoned in Israel more than a decade ago, he explained to an Israeli official a theory now central to the war in Gaza.

Sinwar said what Israel considered its strength – that most Israelis served in the army and soldiers held a special status in society – was a weakness that could be exploited, said Yuval Bitton, who spent time with Sinwar as the former head of the Israel Prison Service’s intelligence division.

The idea proved accurate in 2011 when Sinwar was one of 1027 Palestinian prisoners freed for a single Israeli soldier.

Now, Sinwar is holding hostage 138 Israelis, including soldiers, and the Hamas leader is betting he can force the release of thousands of Palestinian prisoners and establish a permanent ceasefire. He’s relying on his judgment of Israeli society after two decades studying it in jail, learning Hebrew, watching the local news and getting inside the Israeli psyche.

But first Hamas has to survive Israel’s powerful and deadly counter-attack. If Hamas has miscalculated, Sinwar could be overseeing the destruction in Gaza of the US-designated terrorist group – and lose his own life.

The gamble has already come with huge costs, including devastation across huge swathes of Gaza and the deaths of about 17,700 Palestinians.

Israel says its plan is to destroy Hamas’s leadership in the strip, including Sinwar, and prevent the group from ever again threatening Israeli communities after the October 7 attacks killed 1200 Israelis, most of them civilians.

Still, after negotiating the release of women and children during a temporary ceasefire that collapsed this month, the Israeli government faces growing pressure to work with Sinwar for the freedom of the remaining hostages.

“He understands that Israel will pay a heavy price,” said Bitton. “He understands this is our weak spot.”

Sinwar’s playbook since becoming leader of Hamas in Gaza in 2017 has been to remind Israelis constantly that they are in conflict with Palestinians, one moment engaging constructively with Israel and the next pursuing violent means for political ends. He has a history of hunting down Palestinian collaborators with Israel, and his approach to the hostage negotiations was viewed by some Israelis as an attempt at psychological warfare.

During the recent hostage negotiations, he cut off communications for days to put pressure on Israel to agree to a pause that would give Hamas time to regroup, according to Egyptian mediators.

When the hostages were released, they were freed in batches each day, rather than in one go, creating a daily sense of anxiety in Israeli society.

Demonstrators gather at a rally in Tel Aviv last Saturday calling for the release of Israeli hostages held by Hamas. Picture: AFP

Sinwar, who is in his early 60s, has since told Egyptian negotiators that the war won’t be over quickly, the way of other rounds of violence in Gaza; he wants to squeeze as much as he can from Israel for the remaining captives.

Sinwar is the main decision-maker in Hamas as the most senior political leader in Gaza, who is working closely with Hamas’s military wing. The head of Hamas’s political bureau, Ismail Haniyeh, is lives in Doha, and his deputy, Saleh Arouri in Beirut. While Hamas’s leadership in normal times makes decisions based on consensus, Israel believes Sinwar and Hamas militants around him in Gaza are more narrowly directing the war.

Spokespeople for Hamas didn’t respond to requests for comment on Sinwar and the group’s strategy.

Following the breakdown of the recent ceasefire, Hamas said the militant group had only hostages who were soldiers and “civilians serving in the army” and that it wouldn’t release more of them until Israel ended its war. The group has said it is willing to free all the hostages in Gaza for all the Palestinian prisoners in Israeli jails, estimated at more than 7000 people.

Israel’s strategy for getting the remaining hostages out focuses on making battlefield gains to force Hamas to release the captives.

Israeli officials’ theory is Hamas was more willing to negotiate on the release of women and children because Israel had invaded Gaza and began to pressure the group militarily.

Israeli forces are fighting in Khan Yunis, where Sinwar grew up, and this week surrounded his house, a largely symbolic move as he is believed to be hiding elsewhere underground.

Israel has vowed to kill Sinwar and all of Hamas’s top leadership, but senior officials have sent mixed messages over whether the government would be open to allowing lower-level Hamas fighters out of the strip.

One of the reasons Hamas mounted the October attacks was to kidnap soldiers to trade for Palestinian prisoners, according to Palestinian political analysts.

When Sinwar was freed in the 2011 swap, he thought Hamas should have pushed harder for Israel to release Palestinians responsible for bombings that killed Israelis and who were serving several life sentences, said people involved.

As he was freed, Sinwar told those who hadn’t made the cut he would work to get them free, these people said.

“It’s a personal thing,” said Mkhaimer Abusada, a Palestinian who before the war taught political science at Al-Azhar University in Gaza. “He doesn’t feel comfortable leaving jail in 2011 and leaving some of his comrades inside.”

Should negotiations restart, Gershon Baskin, an Israeli peace activist who helped broker the 2011 agreement, said Israel would be unlikely to yield to Sinwar’s demand and give up Palestinians considered the most dangerous. Sinwar, waging war more than a decade after release, epitomised why freeing prisoners who were serving life sentences was a risk for Israelis.

“He is the primary reason why they wouldn’t agree to it,” said Baskin. “They made that mistake once.”

Sinwar has spent more years as a member of Hamas inside prison than out. He was close to Hamas founder Sheikh Ahmed Yassin, who himself had been released in a 1985 swap.

Sinwar worked with his mentor to hunt Palestinian informants suspected of working with Israel, according to Israeli officials. The internal security police set up by Sinwar was a forerunner of Hamas’s military wing, Izz ad-Din al-Qassam Brigades, these Israeli officials said.

In 1988, being interrogated by Israelis, Sinwar explained how he rounded up a suspected Palestinian collaborator when the man was in bed with his wife. He blindfolded the man, called Ramsi, drove to an area with a freshly dug grave where Sinwar strangled Ramsi with a keffiyeh, a symbol of the Palestinian cause.

“After strangling him, I wrapped him in a white shroud and closed the grave,” Sinwar said

In another incident, Sinwar said he believed the brother of a Hamas operative was collaborating with Israelis, according to Michael Koubi, who was one of those who first interrogated Sinwar. Sinwar said he asked the Hamas operative to invite his brother to a meeting, and they put him in a grave and buried him alive, Koubi said.

Koubi said the Hamas leader confessed to killing 12 Palestinians, but none had been working with Israeli authorities, Koubi said.

As early as 1989, Sinwar told his interrogator he was planning to establish units that would conduct raids into Israel to kill and capture people, Koubi said.

Sinwar also was involved in the abduction and murder of two Israeli soldiers, according to the Israeli military. He was given several life sentences and spent 22 years in jail.

Hamas was in its infancy when Sinwar was jailed. It had evolved in Gaza from Egyptian Islamist and social movement the Muslim Brotherhood. In the year he was arrested, Hamas issued a charter of principles that included a goal of destroying Israel.

In 2004, he appeared to develop neurological problems, speaking unclearly and struggling with walking. Doctors examined him, finding an abscess in the brain that threatened his life. After a successful operation Sinwar thanked the doctors for saving his life, former prison officials said.

Sinwar gave Israeli officials the impression he wanted a halt to violence – at least in the short term.

Hamas operatives in 2006 surprised Israeli soldiers at a command post on the border of the Gaza Strip, kidnapping 19-year-old Gilad Shalit. One of the people responsible for orchestrating the kidnapping, according to Israeli officials, was Sinwar’s younger brother, Mohammed. Talks about freeing Shalit dragged on for years.

In prison, Sinwar and his fellow prisoners spent most of their lives in cells of three to eight people, getting out for two sessions a day. They taught each other English and Hebrew and read history and the Koran.

During negotiations between Israel and Hamas over the release of Shalit, Sinwar was influential in pushing for the freedom of Palestinians who were jailed for murdering Israelis.

He wanted to release those who were involved in bombings during the second intifada that had killed large numbers of Israelis, such as at a hotel on a Jewish holiday that initially killed 19 and became known as the Passover Massacre, according to Baskin and an Egyptian official, who helped broker the deal.

Sinwar was so maximalist in his demands, Israel put him in solitary confinement to curtail his influence within Hamas, the Egyptian official said.

Israel eventually released some Palestinians who had committed murders and were considered dangerous, including Sinwar, who only just made the cut to get out because Israelis had reservations about releasing him, Baskin said.

“Releasing him was the worst mistake in Israel’s history,” Koubi said. A week after release in 2011, Sinwar told the Safa Press, a Palestinian news agency, the best option for freeing prisoners left inside was to kidnap more Israeli soldiers.

He arrived back in Gaza to a very different strip. Hamas ruled it after wresting control from the internationally recognised Palestinian Authority. The enclave was fenced off from the rest of Israel.

Sinwar again exerted influence within Hamas. During the war in 2014, he was involved in rounding up and killing suspected Palestinian informants for Israel. Hamas called the killings Operation Strangling Necks, according to Amnesty International, which later documented the deaths.

One of those found dead and bullet-ridden during the conflict was former Hamas spokesman Ayman Taha, according to Amnesty International. Taha had been a liaison between Hamas and Egyptian intelligence, according to Egyptian officials, who believe Sinwar ordered his death over concerns he was leaking information about Hamas’s relationship with Iran. Hamas at the time said Taha appeared to have been killed in Israeli airstrikes.

In 2016, Sinwar was involved in a decision to execute a senior commander of the armed wing, Mahmoud Ishtaiwi, according to Israeli and Egyptian officials and a person close to the murdered commander.

The exact reasons aren’t clear. Egyptian officials say Sinwar arrested Ishtaiwi and convinced Hamas he was a spy. A Hamas official said the commander was an informant for Arab countries. Ishtaiwi told his family Mohammed Deif, the head of the armed wing, had visited him and ordered other Hamas officials to release him, the person close to Ishtaiwi said. He was killed anyway for “behaviour and moral” crimes.

A year later, Sinwar was voted as leader of Hamas in Gaza, with other leaders assuring members he wouldn’t drag the group into new rounds of internal and external violence.

Sinwar again said publicly Hamas was committed to the release of every Palestinian prisoner in Israeli jails. He soon sought to reconcile Hamas with the Palestinian faction that governed the West Bank, warning he would “break the neck” of anyone who stood in the way. Those talks failed, complicated by internal divisions.

In 2021, Sinwar won a second term as Hamas leader in Gaza, again vowing to liberate Palestinian prisoners. In May that year, Hamas fired rockets on Jerusalem helping spark an 11-day conflict.

The death and destruction wrought in the conflict created a sense among the Israeli security establishment that Hamas was deterred and that Sinwar wouldn’t attempt to attack because he was more focused on building the strip economically.

October 7 disproved that. While the initial lightning attack proved a success for Hamas, Sinwar made two mistakes, according to Amos Gilead, a former Israeli senior defence official. He thought the attack would start a regional war involving Iran and Hezbollah, and that Israel wouldn’t invade Gaza to kill the Hamas leadership.

“Now his strategy is to gain time,” Gilead added. “But we don’t have any choice other than to destroy him.”

The Wall Street Journal