It was their first meeting with the new president, and the dozen or so Jewish leaders picked to attend had made an agreement among themselves: No arguing — either with each other or their host.

The pledge would be hard to keep.

Five weeks earlier, President Obama had traveled to Cairo to ask for a “new beginning” between his government and an Islamic world angry about the United States’ wars in two Muslim nations and its perceived favoritism toward Israel. Now, he was calling in these influential Jewish leaders to explain his thinking on the Israeli-Palestinian conflict.

As they gathered in the Roosevelt Room that afternoon, July 13, 2009, there was mounting concern about Obama.

In a very public way, the president had been asking Israel’s government to stop building Jewish settlements in the occupied West Bank and East Jerusalem, hoping that political sacrifice by the Israeli leadership would bring the Palestinians to the peace table. In Cairo, he had even called Israel’s continuing construction on land that Palestinians view as their future state “illegitimate.”

According to three people who were at the meeting, and to notes recounted by one of them, Obama sought to reassure the skeptical attendees, telling them, “Don’t think we don’t understand the nuances of the current issues. We do.”

But it was his response a few minutes later that came to define his administration’s relationship with Israel — and the reason many in the room that day, and even more outside of it, believe that his attempts to bring the two sides together failed in his first term.

“If you want Israel to take risks, then its leaders must know that the United States is right next to them,” Malcolm Hoenlein, the executive vice chairman of the Conference of Presidents of Major American Jewish Organizations, told the president.

Obama politely but firmly disagreed.

“Look at the past eight years,” he said, referring to the George W. Bush administration’s relationship with Israel. “During those eight years, there was no space between us and Israel, and what did we get from that? When there is no daylight, Israel just sits on the sidelines, and that erodes our credibility with the Arab states.”

Obama’s Muslim middle name, former anti-Zionist pastor in Chicago and past friendships with prominent Palestinians had shadowed his presidential campaign. He wanted to restore the United States’ reputation as a credible mediator. To do so, he believed that he needed to regain Arab trust — and talk tough to Israel, publicly and privately.

This was the change that Obama had promised — a new approach to old problems. But the stunned silence of Jewish leaders around the table that day suggested the political peril he would face along the way.

“We believed from that point that we were in for problems,” said Abraham Foxman, the national director of the Anti-Defamation League, who attended the meeting. “And we were right.”

The way Obama managed the Israeli-Palestinian issue exhibited many of the hallmarks that have defined his first term. It began with a bid for historic change. But it foundered ultimately on his political and tactical misjudgments, on a lack of trusted relationships and on an outdated view of a conflict that many of his closest advisers imparted to him. And those advisers — veterans of the Middle East peace issue — clashed among themselves over tactics and turf.

The enduring traits of the conflict, whose resolution Obama elevated to “a vital national security interest of the United States,” made it particularly resistant to his preferred methods of diplomacy. His appeals to the shared interests of countries at war and at peace have achieved some success, including in Africa, Southeast Asia and Latin America.

But the Israeli-Palestinian conflict — haunted by the Holocaust and the perceived injustice of a Palestinian land lost in war — resisted the natural give-and-take of negotiation that Obama counted on. It is a conflict more bound up in domestic politics than any other foreign policy issue, which he learned first in his 2008 campaign and later in the Oval Office.

Obama’s inability to bring Israelis and Palestinians together is especially problematic today, as the Arab Middle East remakes itself and Israel, more isolated than ever, weighs a military strike against Iran. Secretary of State Hillary Rodham Clinton is scheduled to head to Israel this week. And Republican presidential contender Mitt Romney is planning to visit later this month, injecting Obama’s record on the Israeli-Palestinian issue into the heart of a fierce campaign.

“I know that many are frustrated by the lack of progress,” Obama said last fall at the U.N. General Assembly. “Peace is hard work.”

Battling Clinton in the 2008 Democratic primaries, Obama faced long odds contending for Jewish support. His middle name, Hussein, increased the already formidable challenge she posed for the Jewish vote, mostly by raising suspicions about his past and his religious character.

“The bar was higher for him,” said Ben Rhodes, who wrote Obama’s foreign policy speeches during the campaign and is now a deputy national security adviser. “He faced a level of scrutiny — and, frankly, a level of dishonesty in politics — that he had to answer to.”

In February 2008, as the crucial Ohio primary approached, Obama met in Cleveland with about 100 Jewish community leaders, hoping that a candid conversation would dispel some of the concerns rising on the campaign trail.

As a candidate of change, he made clear that he was willing to say things that his predecessors were not.

“I think there is a strain within the pro-Israel community that says unless you adopt an unwavering pro-Likud approach to Israel that you’re anti-Israel,” Obama said, referring to a hawkish Israeli political party that did not recognize a Palestinian right to a state. “That can’t be a measure of our friendship with Israel.”

A little over a year later, Obama was working with the Likud party chief, Benjamin Netanyahu, who was elected Israel’s prime minister for a second time not long after Obama took the oath of office.

The weeks-long war between Israel and armed Palestinian groups in the Gaza Strip had been over officially for two days.

But Obama had promised during the campaign that he would begin a push for peace at once, regardless of the regional mood. On his second day in office, he named former Senate majority leader George J. Mitchell (D-Maine) as his special envoy for Middle East peace.

At 74, Mitchell was the embodiment of the Washington political establishment, noted for his mediation of the centuries-old sectarian strife in Northern Ireland.

But he had Middle East experience as well. In 2000, as the second, more brutal Palestinian intifada worsened, President Bill Clinton dispatched Mitchell to the region. He wanted recommendations on how to end the violence and begin negotiations.

In a report published in May 2001, Mitchell wrote that “a cessation of Palestinian-Israeli violence will be particularly hard to sustain unless [the government of Israel] freezes all settlement construction activity.”

It was the same recommendation he would make to Obama eight years later.

Within a week of his appointment, Mitchell was on a plane to Europe and the Middle East for a “listening tour.”

To Obama and Mitchell, it was a propitious time, despite the recent Gaza war. Never before had the governments of the Sunni Muslim kingdoms, from Saudi Arabia to Jordan, shared more strategic interests with Israel. The reason was the common threat of Shiite Muslim Iran, which leaders in Riyadh and Jerusalem held in near-equal disdain.

In the words of one senior administration official, Mitchell’s plan was to “expand the chess board” — that is, to ask Israel and the Palestinians to return to direct talks and to ask the Arab states to make symbolic gestures to show Israel it was serious about a wider peace.

The approach captured the essence of Obama’s view of foreign policy: everyone gives a little, everyone gets a little. And several senior administration officials believed that Obama, after a historic election at home and rock-star popularity abroad, would be able to persuade traditionally recalcitrant Middle East leaders to agree.

But no Arab leader showed an interest in helping Obama with Israel. Mitchell did hear something else on his trip — that a freeze on Israeli settlement construction would send a strong signal that the new president wanted to make a difference.

An estimated 450,000 Israeli settlers live in the West Bank and East Jerusalem — land occupied by Israel in the 1967 Arab-Israeli war. With each new house or apartment building, the land that Palestinians view as their future state shrinks. Israel annexed East Jerusalem soon after the 1967 victory — a move not recognized internationally — and no Israeli government had frozen construction there. Asking for a moratorium from the just-elected Netanyahu, a traditional hawk at the head of a narrow hawkish coalition, would be an enormous request.

At the time, Obama made clear to close advisers that he, in the words of one of them, wanted “to demonstrate that he could change Israeli behavior on the ground” to strengthen U.S. credibility.

Mitchell agreed with the approach, acknowledging that no U.S. president had ever asked an Israeli leader for such an extensive settlement freeze.

“We got what we wanted,” said Jeremy Ben-Ami, the president of J Street, a rival advocacy group to the American Israel Public Affairs Committee. Many of its donors are Obama supporters. “We got a president who seemed to ‘get it.’ We got a commitment to deal with this on Day One. And we got George Mitchell.”

I n mid-May 2009, Netanyahu made his way to Washington for his first meeting with Obama as president. The leaders did not know each other well — one senior administration official described Netanyahu as “essentially a Republican” — and their outlook on the future shape of Israel differed starkly.

Netanyahu had not declared his support for a two-state solution. Unsure what reception he would receive, he found out quickly when the leaders met May 18 at the White House.

“Settlements have to be stopped in order for us to move forward,” Obama told reporters in the Oval Office, Netanyahu by his side.

Netanyahu was stunned by the encounter, according to Israelis, Americans and Palestinians who were later briefed on the meeting. The next day, he headed to Capitol Hill for a talk with Jewish members of Congress, a group that gathered a couple of times a year.

It was clear to some present, as they recounted the meeting, that Netanyahu was looking for support to take on Obama over his demand for a settlement freeze.

“What he received was a distinct surprise to him, which was unified support from many longtime friends of Israel for the president’s policy,” said former congressman Robert Wexler (D-Fla.), who attended the meeting after serving as a liaison between Obama and Jewish voters during the campaign. “He was clearly taken aback.”

Obama’s relationship with Netanyahu was complicated by more than their politics. As with many aspects of the Israeli-Palestinian conflict, it involved a history that Obama had little to do with.

Netanyahu believed that some of Obama’s Middle East advisers carried what one Israeli diplomat described as a “Clinton-era grudge,” a bias against Netanyahu that would transfer to Obama.

Bill Clinton and Netanyahu clashed repeatedly over the general faltering of the 1993 Oslo Accords that had brought a measure of Palestinian self-government in the territories.

But they found ways to compromise, and Netanyahu, fearing a politically costly falling-out with a U.S. president, agreed to some Palestinian concessions. His decision probably cost him the 1999 election.

Hillary Clinton, Mitchell, Chief of Staff Rahm Emanuel and Dennis B. Ross — a Middle East adviser to Obama during the 2008 campaign who joined his administration as a State Department adviser on Iran — were veterans of the Clinton years.

According to former administration officials and outside advisers briefed on some White House meetings, Emanuel, in particular, thought Netanyahu could be pressured to make concessions, just as he had in the 1990s.

Emanuel’s father was born in Jerusalem and, before the state of Israel was created in 1948, belonged to the Irgun, a Jewish paramilitary movement classified as a terrorist group by the British forces it fought. Emanuel served as a civilian volunteer for the Israel Defense Forces during the 1991 Persian Gulf War.

He often told others that he believed his view was consistent with that of the Israeli political center, which had traditionally disliked the settlement project because of its cost and security risks and the moral questions it raised about the occupation of Palestinian land. He also had an outsize say in the Obama administration about Israel policy.

“I have some very smart people advising me on this,” Obama told the Jewish leaders in that first meeting at the White House in July 2009, turning to Emanuel.

“We understand there is a profound political edge to Israeli politics. Rahm understands the politics there and he explains them to me.”

To many in the administration, Emanuel’s instinct was one of “tough love” toward Israel.

“But his depth may not have been as grounded in the realities of the current conflict as it should have been,” said a senior administration official, who worked on the Israeli-Palestinian issue.

Netanyahu had changed since the 1990s, and so had the Israeli public. From his experience with Clinton, Netanyahu learned that he could not afford to lose his base. For him, a fight with a U.S. president pressuring Israel was a safer political bet than it once had been.

How to manage the region’s key leaders would become an occupation of Obama and his team, and Netanyahu was not the only Middle East veteran generating concern. The other was Mahmoud Abbas, the 77-year-old Palestinian leader who had spent a lifetime promoting an independent Palestine.

Abbas had once broken with the Palestinian leadership on principle over the violence of the second intifada. Now he ran a Palestinian national movement divided between his secular Fatah party and the Islamists of Hamas.

On the eve of Abbas’s arrival in Washington in late May 2009 for his first meeting with Obama, Hillary Clinton provided an unscripted push to the Palestinian leader’s position.

At a State Department appearance with the Egyptian foreign minister, Clinton, speaking for Obama, said, “He wants to see a stop to settlements — not some settlements, not outposts, not ‘natural growth’ exceptions.’

“That is our position,” she said, outlining a demand publicly stronger than any to date. “That is what we have communicated very clearly.”

White House officials acknowledged recently that her comments were a mistake. But the president declined to soften that position when he had a chance.

Obama’s twin meetings with Netanyahu and Abbas that May were steps along the path to Cairo, where he intended in early June 2009 to deliver the signature foreign policy address of his first term. From inside the domed main hall of al-Azhar University, a centuries-old seat of Islamic learning, Obama, the son of a lapsed Muslim father, spoke candidly.

He warned Palestinians to end hateful anti-Israel incitement, rejected the official strains of Holocaust denial, and condemned suicide terrorism, saying that “Palestinians must abandon violence.”

“On the other hand, it is also undeniable that the Palestinian people — Muslims and Christians — have suffered in pursuit of a homeland," Obama said. “They endure the daily humiliations, large and small, that come with occupation.”

Using the term “occupation” for the Israeli military authority over the West Bank and other areas seized in the 1967 war sent a powerful message.

“America will align our policies with those who pursue peace,” Obama said, in what to Israelis sounded like a warning. “And we will say in public what we say in private to Israelis and Palestinians and Arabs.”

The speech and spectacle surrounding it electrified much of the Muslim world — and alarmed many Jews.

Around midnight, after touring the Sphinx and pyramids, Obama headed to Dresden, Germany, for a meeting with German Chancellor Angela Merkel.

The U.S. delegation did not stop in Jerusalem, as some Israeli officials had hoped it would. The trip had a planned symmetry, as White House aides recently described, that a few days in Israel would have disrupted.

After a quick meeting with Merkel, Obama headed for the hilltop camp of Buchenwald, an iconic element of the genocidal Nazi network. He met the Nobel Peace laureate Elie Wiesel on his arrival. Wiesel spent time at the camp as a child. His father died there.

Of the horrified liberators who arrived at the camp decades earlier, Obama said, “They could not have known how the nation of Israel could rise out of the destruction of the Holocaust and the strong, enduring bonds between that great nation and my own.”

For the small number of people who witnessed that still afternoon, the memory was indelible. It was also a miscalculation, a sign that the president knew less about the historic shape of the Israeli-Palestinian story than he thought. Some prominent Israelis and Jewish supporters said Obama, in his somber remarks at the gates of the camp, suggested that the state of Israel emerged as a moral response to the Holocaust. But most Israelis believe the state’s legitimacy is rooted in the Bible and Hebrew texts of its people, a central tenet of Zionist thought.

“What you saw, at several turns during Obama’s management of this, was a complete lack of an emotion-based relationship with Israel,” said a former Palestinian political adviser to the Palestine Liberation Organization, who spoke on the condition of anonymity to provide a candid view.

“The Cairo speech was excellent, important,” the adviser said. “But it didn’t preclude a Jerusalem speech. It didn’t show any emotional smarts.”

The dilemma Obama faced came to be known among American Jews as “the kishkes question,” a Yiddish expression referring to what he “felt in his gut” toward Israel.

“American Jewish supporters of Israel have gotten used to presidents conveying a sense of solidarity with Israel in ways that are greater than the sum of specific policies,” said Nathan J. Diament, the executive director for public policy of the Union of Orthodox Jewish Congregations of America and an Obama acquaintance at Harvard Law School. “President Obama, despite making pro-Israel statements, had trouble finding his voice to express that sense early in his presidency.”

George W. Bush did not visit Israel until late in his second term, and Ronald Reagan did not visit at all — yet neither faced the same doubts about their attachment to the nation. Neither did Bill Clinton, a master empathizer who eulogized Israeli Prime Minister Yitzhak Rabin after his 1995 assassination.

Returning from the trip, Obama spoke by phone to Netanyahu on June 8, 2009, and, by all accounts, the call was not a happy one. Netanyahu was resisting the settlement freeze request — managed by Mitchell, who was due to arrive in Israel the next day for his fourth visit to the region.

Less than a week later, Netanyahu endorsed, for the first time, the Palestinian right to an independent state during a national address. Obama immediately called the speech “an important first step,” even though it contained so many caveats that Palestinians dismissed it as an empty gesture.

Not long after, Obama assembled the Jewish leaders in the Roosevelt Room in July for that first meeting after a difficult few months of early diplomacy.

Foxman, the Anti-Defamation League leader, expressed concern that Obama was not being “evenhanded” when it came to asking for sacrifices from Israel and the Palestinians.

“Abe, you are absolutely right and we are going to fix that,” Obama told him, saying that “the sense of evenhandedness has to be restored.”

Obama’s view of the conflict broke from Bush’s approach, which he believed overtly favored Israel and damaged the United States’ ability to play the role of trusted mediator. Bush developed a close relationship with then-Prime Minister Ariel Sharon, a Likud member for decades until breaking off to form a centrist party known as Kadima. He even took Sharon to his ranch in Crawford, Tex., before Sharon’s unilateral withdrawal of Israeli troops and settlers from Gaza in 2005.

With what they viewed as mixed results from the Bush years, some Jewish leaders in the meeting that day disagreed with Obama’s assessment that only by creating some public distance with Israel could diplomatic progress be made with the Palestinians.

“The case he was trying to make was that the United States will be a better partner to Israel if it has more credibility with the Arab states, that we will be a better, more useful friend to Israel if we have more friends in the Arab world,” Rhodes said.

But the continuing Israeli resistance to a settlement freeze, growing tension with American Jews and a lack of progress with Arab leaders concerned Obama, who needed to make a change.

In late May 2009, James L. Jones, the national security adviser, called Ross, who was running the Iran portfolio at the State Department. Ross served in the Clinton administration, and was tapped early by Hillary Clinton to work for her at State.

He was among the most experienced U.S. diplomats concerning Middle East peace efforts and had proved over the years to be a voice within administrations for reducing pressure on Israel.

“Did you hear the president wants to see you tomorrow?” Jones asked Ross, instructing him to arrive at the White House the next morning without telling him why.

In their meeting, Obama informed Ross that he wanted him to “quarterback” all Middle East policy, including that involving Iran.

Ross was inheriting a policy that he considered politically unfeasible. He believed the haggling over the freeze was wasting Obama’s political capital in a region that once had high hopes for his presidency.

“We had adopted a hard and firm position on this by then,” Ross said in an interview, echoing what he told the president. “The problem was that it put the emphasis on one issue when it wasn’t the only, or even most important, issue and, in any case, needed to be put in context.”

Ross arrived in the West Wing in July 2009, the same month Obama held his first meeting with Jewish leaders. The initial question Ross wanted answered was: Who developed the settlement-freeze idea and was it possible to alter it? What he got was finger-pointing and no clear reply, even among senior officials.

With Mitchell in the region or at his home in Maine, Ross accumulated more influence on the issue as the weeks wore on and progress remained elusive.

“What’s the strategy here?” Obama asked constantly in meetings with Mitchell, Emanuel and others pushing for the settlement freeze, according to participants. “I see you want the moratorium, but how does it get us where we want to be? Tell me the relationship between what we are doing and our objective.”

The senior staff rivalry intensified as the questions persisted.

Administration officials said Mitchell and Ross clashed over responsibilities and policy approach, and Israel appeared to see its influence rise within the West Wing.

To those on Mitchell’s staff, there was confusion about how he could be so inept at the internal White House politics. He had been a skilled Senate majority leader, adept at political infighting.

“So it surprised me that it so surprised him that you have to do that in the job he was in,” said one administration official involved in Middle East policy.

I n November 2009, Netanyahu announced a 10-month freeze on settlement construction in the West Bank, excluding several hundred new permits that, much to Mitchell’s displeasure, Israel shoe-horned in before the deadline.

But Netanyahu would not agree to a moratorium in East Jerusalem, prompting Abbas to call the freeze meaningless. He would not participate in new talks, despite pressure from some of his own advisers to do so.

“I told him that you have to help the president to help you,” said a Palestinian adviser to Abbas at the time, who, like others, agreed to speak on the condition of anonymity to describe private conversations. “He looked at me and said, ‘He’s the president of the most powerful country in the world. He doesn’t need my help.’ ”

The result: an angry Netanyahu, who had made a political sacrifice without reciprocation from the Palestinians. Israeli officials wondered why Obama was not applying the same pressure they had been feeling for months to the Palestinian leadership — and so did Israel’s supporters in the United States.

As the midterm election year of 2010 began, Obama and his political advisers decided that it was time to mend some fences with nervous Jewish voters.

Obama tapped Vice President Biden in March to go to Israel, where his relationships with Israeli and Palestinian leaders dated back decades.

As Biden arrived in Tel Aviv on a two-day mission to reaffirm U.S.-Israeli relations, he was greeted by Mitchell, who had just announced that Israelis and Palestinians had agreed to begin indirect talks.

But Biden soon received disturbing news.

Israel’s Interior Ministry announced the construction of 1,600 new housing units in northern East Jerusalem — a community called Ramat Shlomo — that undermined Mitchell’s success at bringing the two sides closer together.

“It may have been a coincidence, but if so, it was an extraordinary and unfortunate coincidence,” Mitchell said in an interview.

For Biden, who was scheduled to dine with Netanyahu that evening, this was a diplomatic embarrassment. The vice president wanted to issue a statement from Jerusalem, but its wording was the subject of intense debate among his advisers and those back at the White House. Biden showed up for dinner at Netanyahu’s residence more than an hour late, and the statement he finally issued used the term “condemn,” the most severe under consideration. As Ross put it later, according to officials familiar with the debate, he believes that term should be used only to describe events related to terrorism.

Referring days later to the settlement announcement in his speech at Tel Aviv University, Biden noted that he had “condemned it immediately and unequivocally” at “the request of President Obama.”

As Biden flew home that day, his aides believed the episode was over. Some joked that the new Israeli settlement should be renamed “Biden Towers.”

While the vice president was in the air, Obama had breakfast with Secretary Clinton at the White House. By the end of the meal, Clinton returned to the State Department, where she got Netanyahu on the phone.

For about 45 minutes, according to senior State Department and White House officials, some of whom witnessed the call, Clinton sharply criticized the prime minister, calling what had happened a humiliation to the United States.

“She told him that this had created a problematic atmosphere and that we’re looking to you, as a friend, to take some concrete steps to make it right,” said a senior State Department official, who spoke on the condition of anonymity.

Clinton had several items that Obama wanted Netanyahu to address. While they have not been made public, Israeli and U.S. officials acknowledged recently that Netanyahu effectively froze new building in East Jerusalem after the Clinton call.

Nearly two weeks later, Netanyahu, reading polls that showed him with a far higher approval rating than Obama in Israel, traveled to Washington for an annual policy conference of the American Israel Public Affairs Committee .

“The Jewish people were building Jerusalem 3,000 years ago and the Jewish people are building Jerusalem today,” Netanyahu said in his March 2010 speech, openly defying Obama.

“Jerusalem is not a settlement,” he said to sustained applause. “It is our capital.”

Obama’s mind was elsewhere. Earlier that day, he had signed the Affordable Care Act, his historic and politically expensive health-care legislation.

But Israeli officials wanted a meeting with Obama to play down their dispute over “Biden Towers,” despite Netanyahu’s statement, which the president later told a private audience he found “belligerent.”

Obama agreed to meet with Netanyahu. But the White House did not allow photos of the encounter, denying Israel’s leader an image to reassure his public that all was right with the U.S. president.

“We did not want to reward the Israelis after the Biden visit fiasco with a make-up meeting at the White House,” said a senior administration official involved in the planning. “But more important, the meeting came on the same day Obama signed the health-care law,” the official continued. “That was the White House message of the day, and we weren’t looking to lift up Israel as an issue at that moment.”

The open anger between Israel and the president frightened some congressional Democrats who were concerned about a tough election environment. In May 2010, they asked Emanuel for a meeting with the president.

In the Eisenhower Executive Office Building, 37 Jewish senators and House members sat around tables set up in a “U” shape. No one could recall a larger meeting between a president and Jewish lawmakers. The unanimous support for Obama’s Israel policy that many of those same members expressed to Netanyahu a year earlier had turned to worry.

“At the heart of our concern was the focus on settlements, undertaken without congressional consultation, as much had been with this president over the past three years,” said one participant, who is generally supportive of Obama.

“My policy on settlements is no different than George Bush’s policy toward settlements,” Obama told the members, according to notes of the meeting shared by a participant. “But I won’t wink and nod.”

In his trips to the region, Mitchell urged Abbas to begin direct talks, even as he agreed with the Palestinian leader that Israel’s partial freeze was imperfect.

Abbas was facing pressure from his advisers, who argued that Netanyahu had taken a political risk under pressure from Obama.

About nine months after the Israeli settlement freeze was announced, Abbas decided the time was right to talk. The plan was to inaugurate the talks at the White House on Sept. 1, 2010. But a problem loomed. Israel’s settlement moratorium was set to expire at the end of September, and Netanyahu had made clear, despite Obama’s requests, that it would not continue.

A debate unfolded over whether to announce the direct talks in a less formal way. Obama’s communications advisers, in particular, believed it was a bad idea to set unrealistic expectations with a lavish opening ceremony. But, according to three senior administration officials involved in the debate, Ross pushed hardest for a White House event. He prevailed.

On the evening of Sept. 1, from the East Room, Netanyahu turned to Abbas and said, “you are my partner in peace.” The talks began.

Three weeks later, Obama told the U.N. General Assembly in his annual address that “when we come back here next year, we can have an agreement that will lead to a new member of the United Nations — an independent, sovereign state of Palestine, living in peace with Israel.”

Within days, Israel’s settlement freeze expired and with it the direct talks. After a year and a half of politically costly pressure on Israel, Obama had nothing to show for it, except far less capital to work with at home and a damaged reputation among the Middle East veterans directly involved.

“Around this time, an image was being created that it was pain-free to say no to the United States,” said a former Palestinian adviser to Abbas, who is known informally as Abu Mazen. “There was no sense of awe around the president — and that is essential to the peace process. That is what informed Abu Mazen’s thinking about Obama.”

In January 2011, Obama called Abbas with a president-to-president request.

After the direct negotiations collapsed, Abbas urged Arab nations to submit a resolution to the U.N. Security Council condemning Israeli settlement building on occupied land and calling for a new freeze.

Abbas was planning to secure a resolution at the General Assembly in September that would recognize the state of Palestine. Despite it being consistent with U.S. policy on settlements, a senior administration official said, “We knew this resolution would be a prequel to the statehood debate coming in the fall, and we wanted to head it off.”

In a call that lasted about an hour, Obama urged Abbas to withdraw the settlement resolution, warning that Congress might eliminate roughly $450 million in annual U.S. aid to the Palestinians if he went ahead.

Abbas told him flatly that he planned to proceed. A few weeks later, Obama used the U.S. veto on the Security Council for the first time, killing the resolution and infuriating the Arab world he had cultivated.

By then, the Arab Spring was unfolding in ways that took the administration by surprise. Decades of U.S. policy in the Arab world, an unpopular bargain that often placed stability ahead of democratic rights, were shattering.

Obama had called for democratic reform in Cairo, but as allied governments fell chaotically across the wider Middle East, he and his advisers saw as much peril as promise in the changes. How and when to get on the side of the street-based reform movements, whose leaders were largely unknown, was the central question they faced.

The Obama administration prepared for new Islamist governments in the region — all of them likely to be hostile toward Israel — and turned its back on several secular autocratic allies. That included Egyptian President Hosni Mubarak, one of only two Arab leaders whose countries had a peace treaty with Israel.

As Arab leaders tumbled, Obama and his senior advisers debated how to speak about the American stake in the new Middle East. Among the central questions for Obama was how, if at all, the changes should be related to the Israeli-Palestinian conflict.

Mitchell and Ross disagreed over how Obama should talk about the issue. A speech was scheduled for the eve of a Netanyahu visit to the White House, and as Obama prepared for an official visit to Europe.

Ross argued that Obama should give not one but two addresses, fearing that the points he intended to make about Arab democratic reform would be overwhelmed if the Israeli-Palestinian conflict were introduced. He was alone in that view.

With that decided, a larger debate emerged over how far Obama should go in setting out his view of an eventual peace agreement. He had been considering doing so for months, particularly at times when Mitchell was hitting brick walls in the region.

Mitchell led a group of advisers in arguing that Obama should endorse new direct talks based on the pre-June 1967 lines, and acknowledge that swaps of land from inside what is now Israel would be made to account for Israeli settlements in the territories.

He should also emphasize Israel’s security requirements, as he frequently did in speeches and in his requests for increased military aid in Congress, they said.

Where Mitchell differed strongly from Ross was that he wanted Obama to take on the conflict’s two most vexing issues: a division of Jerusalem, the holy city that Israelis and Palestinians both claim as their capital, and the right asserted by millions of Palestinian refugees and their descendents to return to land inside Israel.

“Mitchell wanted Obama to be as bold as possible, to send a signal to the parties and the Arab world more broadly that the United States wanted change on this core issue of historic contention,” said a senior Obama adviser involved in the debate.

Mitchell lost, and announced his resignation six days before Obama delivered the speech at the State Department.

“I left because I had told the president from the start I would only do it for two years or so,” Mitchell recalled. “But that wasn’t the only reason I left.”

Ross won largely because Obama, as has been his penchant on other issues, essentially split the difference. He decided to talk about borders and security, but not Jerusalem and refugees.

Before diplomats at the State Department on May 18, 2011, Obama said that for Israelis, the conflict “has meant living with the fear that their children could be blown up on a bus or by rockets.” He added, “For Palestinians, it has meant suffering the humiliation of occupation.”

“Yet expectations have gone unmet,” he said. “Israeli settlement activity continues. Palestinians have walked away from talks.”

What Obama intended to say on the Israeli-Palestinian question was so closely held in the days before the speech that, as drafts of the address were circulated for comment, the section on that issue was left blank.

Netanyahu, as he prepared to leave for Washington, felt blindsided by how Obama framed future talks about territory. Israeli officials, led by the historian Michael Oren, Israel’s ambassador to Washington, seized on Obama’s reference to the 1967 lines.

Obama mentioned that land swaps probably would be necessary to make up for territory taken by Israeli settlements, a formulation Bush also had used.

But the Israelis claimed that the president had in a single morning changed decades of U.S. policy on how the negotiations would unfold on the final borders of Israel.

At the heart of the Israeli anger was Obama’s unspoken suggestion that the starting point for talks would begin with the original 1967 lines, not the new Israeli settlement boundaries that extend deep into the West Bank.

One senior State Department official said Netanyahu and other Israeli officials intentionally misunderstood Obama’s position to score political points with a right-trending electorate at home. As this official put it, “Friends do not treat friends that way.”

In the Oval Office the next day, Obama and Netanyahu sat side by side. After the president’s brief welcome, the prime minister leaned into him with cameras catching every moment. He suggested bluntly that Obama had little, if any, understanding of how peace efforts and the broader Middle East worked.

“I think for there to be peace, the Palestinians are going to have to accept some basic realities,” Netanyahu told him.

Publicly calm, Obama was privately irate at the treatment. As a senior Obama adviser involved in the meetings said, “I can think of no other time when a president has been lectured to in the Oval Office.”

Obama’s ire didn’t melt easily.

His public push for peace vanished until September, when he headed off the Palestinian statehood resolution at the General Assembly.

But the issue still dominated the annual gathering of world leaders, where Obama previously had made calls for Israelis and Palestinians to sacrifice for peace. This time, as Republican presidential rivals lined up to criticize his policy toward Israel, Obama had something else in mind.

On his way to the venue on the morning of Sept. 21, 2011, he jotted some additions in the margins of the prepared text.

The phrases, which came so late that he began the address reading from the paper copy because it had yet to be loaded into the TelePrompTer, underscored for an audience usually hostile to Israeli interests the pain experienced by the other side.

“Israel’s children come of age knowing that throughout the region, other children are taught to hate them,” Obama said, delivering the lines he had written on his way to the speech. “The Jewish people carry the burden of centuries of exile and persecution, and fresh memories of knowing that 6 million people were killed simply because of who they are. Those are the facts. They cannot be denied.”

He did not use the words “occupation” or “settlements,” and to many in the hall that day, a president who promised something different in Cairo sounded much the same as his predecessors on an issue that had baffled them.

Ross left the administration two months later for the Washington Institute for Near East Policy, his longtime think-tank home. The fights had been fought. He knew there was not much else he could do.

Last month, Obama gathered another group of Jewish leaders at the White House, this time Orthodox rabbis and lay leaders.

Diament, the Obama law school acquaintance, introduced the president. He called him a man who, like many of the Jewish leaders around the table, advocated for change based on principle.

Diament had not attended the first meeting between Obama and Jewish leaders almost three years earlier, when the president outlined the need to establish credibility with the Arab states.

But to Diament, who had been briefed on that gathering, Obama’s message on this June day was far different.

“My administration is not being evenhanded,” Obama said, according to notes taken by some of the participants. “We are being decidedly more attentive to Israel’s security needs,” a statement that attendees believed was a reference to how the president viewed the eventual terms of a peace deal.

Diament said he thought, “Three years ago ‘evenhandedness’ was the gold standard in Middle East peace-making. Now it is something that is being avoided.”

Where, then, does a president who promised a new approach to the old Middle East and ultimately failed to deliver begin if he wins a second term?

“The president’s view now is that this is about the Israelis and the Palestinians,” said Rhodes, his deputy national security adviser. “These really are their choices to make.”

During the meeting last month, Rabbi ­Shmuel Goldin, president of the Rabbinical Council of America, asked Obama for his assessment of the past three years.

Those in the room had their opinions — on the “kishkes question,” on the need for a close relationship with Israel, and on Palestinian will. Now it was Obama’s turn to explain his view of the work he had done to secure an elusive Israeli-Palestinian peace.

“Mr. President, what lessons have you learned?” Goldin asked.

“That it’s really hard,” Obama said.