The Israelis have granted early release to Palestinian prisoners in the past, including in swaps. The upcoming round, however, has sparked particularly high-pitched debate because it was linked to resuming talks and many of those to be freed were involved in deadly attacks.
Gila Molcho said the release of one of three men involved in the stabbing death of her brother in 1993 was opening old wounds. Her brother, Ian Feinberg, was killed in the European aid office in Gaza City where he was working as a lawyer.
"My brother's blood is being sold for nothing, as a gesture," Molcho said. "On a very personal level, there is pain."
Palestinians argue that those slated for release were acting during a time of conflict, before the two sides struck their first interim peace agreement in 1994, and that Israel should have freed them in previous rounds of negotiations.
"We used violence and the Israelis used violence," said Kadoura Fares, who heads an advocacy group for prisoners and, like many of those to be released, is a member of Palestinian President Mahmoud Abbas' Fatah movement.
Fares noted that the number of Palestinians, including civilians, who were killed by Israeli troops in wars and uprisings over the past two decades far outstrips the number of Israelis killed in Palestinian attacks.
In the first and second Palestinian uprisings, more than 1,200 Israelis and just under 5,000 Palestinians were killed.
The two sides are now making their third major attempt since 2000 to agree on the terms of the Palestinian state alongside Israel. The Palestinians want a state in the West Bank, Gaza and east Jerusalem, lands Israel captured in 1967, but are willing to make some adjustments.
The last round of substantive talks was held in 2008, but a dispute over settlements kept the two sides away from the table until now.
The Palestinians are entering Wednesday's talks with renewed distrust, after Israel promoted Jewish settlements on war-won lands the Palestinians want for their state in three major announcements over the course of a week.
Abbas had insisted on a construction freeze in settlements, deemed illegal by most of the international community, before going back to negotiations. However, U.S. mediators failed to get Israeli Prime Minister Benjamin Netanyahu to comply and Abbas relented.
As compensation, U.S. Secretary of State John Kerry brokered the prisoner release and, according to Abbas aides, assured the Palestinians that the U.S. views Israel's pre-1967 lines as a starting point for border talks, even if Netanyahu does not.
Abbas is returning to talks amid widespread skepticism among Palestinians, but the prisoner release an emotional consensus issue could make up for that.
Tens of thousands of Palestinians have spent time in Israeli prisons since 1967, on charges ranging from throwing stones and membership in outlawed organizations to involvement in attacks. Palestinians tend to view prisoners as heroes, regardless of their acts, arguing they made personal sacrifices in the struggle for independence.
In Israel, many consider those involved in the killings as terrorists, and some of the attacks are engraved in the nation's collective memory.
This includes the death of Amnon Pomerantz, a 46-year-old Israeli reserve sergeant who in 1990 made a wrong turn and ended up driving into Gaza's Bureij refugee camp with his car marked by yellow Israeli license plates.
Pomerantz was stoned and tried to drive away in a panic, but his car rammed into a donkey cart and injured two youngsters. This was followed by another barrage of stones and gasoline-soaked rags that set his car on fire. Pomerantz burned to death.
Another victim is Isaac Rotenberg, who survived the Nazi death camp of Sobibor, fought alongside partisans and made it to Israel after World War II. In 1994, at age 69, the contractor was killed with an ax from behind while at a construction site, his son Pini said, adding he finds it difficult to fathom that one of his father's killers is going free.
"It's painful to pay such a heavy price just as a concession for talks," he said.
In the summer of 1989, al-Haj who made the first list of those to be released was with two friends when they encountered 48-year-old Frederick Rosenfeld, during a West Bank hike, chatted with him and even posed for pictures before stabbing him to death.
Rosenfeld had immigrated to Israel from Washington, D.C. in the late 1960s and eventually moved to the Jewish settlement of Ariel, near the West Bank town of Brukin.
In Brukin, al-Haj's family did not want to speak in detail about Rosenfeld as they decorated his West Bank home with chains of lights ahead of his anticipated homecoming.
"I wish he hadn't killed that man and that he hadn't gone to jail for those long years, but this is God's will," Hamza al-Haj, 55, said of his younger brother. "This was a war time, in which people kill each other. You can't define one as a criminal and one as a victim."
Hamza said his brother was an activist in the first Palestinian uprising, which lasted for six years and ended with a historic accord of mutual recognition between Israel and the Palestine Liberation Organization in 1993.
The family now hopes Mustafa, who earned a bachelor's degree in political science in a correspondence course, can start a family and find a job.
In Gaza's Bureij refugee camp, Fatima Nashabat, 48, said she is counting the hours until the release of her husband, Mohammed, 52, who has spent 23 years in prison as an accessory in the killing of Pomerantz, the reserve soldier.
"Last night, when they said he will be in the first group, our house turned into a big dance floor," said the mother of four. "We were cheering and singing."