As the two leaders look to tamp down the disagreements and distrust that have come to define their relationship, Hillary Clinton can only be crossing her fingers that it all goes well.
That's because Clinton, Obama's former secretary of state and the leading Democratic candidate for president, is looking to shore up support from Jewish voters and donors who have grown wary of Obama's handling of the historically strong U.S.-Israel relationship. And the perception that Clinton would deliver more of the same frayed relations could turn off some of those constituents amid Republican efforts to tie Clinton to Obama's rocky relations with the Israeli premier.
Monday's meeting has been billed as an attempt to turn the page on U.S.-Israel relations after sharp public clashes between the two governments over the Iran nuclear deal the United States completed in July, a culmination of years of discord between the two leaders.
Clinton will have something to smile about if it succeeds.
If Obama and Netanyahu smooth things over -- or at least give that impression -- the headlines emphasizing tension between the Democratic White House and head of the Jewish state could fade, creating more space for Clinton to push the narrative of U.S.-Israel relations in a new direction.
The new direction would be likely to include a reframing of her own rocky episodes with Netanyahu while secretary of state as she emphasizes their longstanding ties and her history of support for Israel.
"The pro-Israel community wants there to be cooperation and collaboration between our two governments, and if the meeting turns out being the reset that both sides look like they want, then that will certainly be beneficial to allies of the President and his political successor," said William Daroff, senior vice president for public policy at the Jewish Federations of North America.
"If Obama and Netanyahu are able to turn the page, reset, have a love fest -- I think it will serve Democratic candidates well," added Daroff, whose organization will host a speech by Netanyahu while he's in town.
The 'designated yeller'
Beyond the Iran nuclear deal, which Clinton endorsed and helped lay the groundwork for, the former secretary of state, by her own account, was the "designated yeller" in the Obama administration when the Israeli government took steps the United States deemed counterproductive to the peace process.
Clinton publicly scolded Netanyahu's government for settlement activity, the treatment of Palestinians and the inflammatory rhetoric of his Cabinet members.
When Israeli officials announced construction of new housing units in largely Palestinian East Jerusalem during Vice President Joe Biden's visit to Israel in 2010, Clinton picked up the phone to lambast the Israeli Prime Minister in a much-publicized 45-minute phone call.
Clinton later termed the timing of the housing announcement "insulting," and Israel's ambassador to the United States at the time, Michael Oren, said the phone call marked a new low in the two countries' relations.
While Republicans will look to use Clinton's harsh statements about the Israeli government to paint her as part and parcel of the Obama administration's frosty relations with Israel, Clinton has pointed to her arguments with Netanyahu as a mark of their longstanding rapport.
"I have a very good relationship with him, in part because we can yell at each other, and we do," Clinton told CNN's Fareed Zakaria last year. "And I was often the designated yeller. Something would happen, a new settlement announcement would come, and I would call him up, 'What are you doing? You've got to stop this.' And we understood each other."
Clinton's relationship with Netanyahu goes back to her time as first lady, when the Israeli leader was first elected Prime Minister.
The Clinton-Netanyahu relationship didn't get off to the best start, set against the turbulent interactions between former President Bill Clinton and the Prime Minister, then in his first term. Before his election, the President clasped hands with Netanyahu opponent Shimon Peres in a photo op less than a month before the 1996 election, giving the appearance of an endorsement.
But Hillary Clinton would later host Netanyahu at the White House, and truly made a name for herself in pro-Israel circles during her time as a U.S. senator from New York. In that office, she worked hard to quell doubts about her pro-Israel bona fides and fought for causes like getting the International Red Cross to include the Israeli equivalent, Magen David Adom, as a member.
But by far her most extensive interactions with Netanyahu came during her time as secretary of state in an Obama administration known for dispensing tough love to the Israeli government as it looked to drive the Israelis and the Palestinians to the negotiating table.
Talks with Netanyahu and Abbas
Clinton did manage to bring Netanyahu and Palestinian Authority President Mahmoud Abbas together in 2010 for what remains the most recent public meeting between the two leaders.
In her book "Hard Choices," Clinton said that despite disagreements, the two "worked together as partners and friends" and said that while she did have to play "the bad cop," she didn't enjoy it.
"It was part of the job," she wrote in the memoir.
Obama, too, has an incentive to smooth the path for Clinton. While making nice with Netanyahu this week will make his last year dealing with the Israeli leader easier, Obama has a concern that will extend far beyond January 2017: his legacy.
Setting up a Democratic successor who will preserve his achievements on domestic and international fronts is high on Obama's list. And Clinton is the Democrat most likely to be in that role.
One of the main drivers behind Obama's plans to mend ties with Netanyahu on Monday is to help the Democratic nominee for president, according to David Makovsky, a fellow at the Washington Institute for Near East Policy who advised Secretary of State John Kerry's efforts to reboot the Israeli-Palestinian peace process.
"2016 is part of the calculus here," Makovsky said. "The closer we get to the election, the more this President is going to put a premium on maximizing the chances for his successor."
Netanyahu's apparent willingness to put the disagreement over the Iran deal behind him to some degree and move forward jointly with the U.S. -- and Obama -- could shield Clinton from blowback on an issue that has divided the Jewish community
"There's definitely some part of the Jewish community that isn't happy with the Iran issue and feels like this is not something that would be good for the country," said Clinton supporter and former Democratic Florida Rep. Ron Klein. "But Hillary, I am quite certain, will be presenting herself independently on what her record has been on Israel."
Downplaying the potential that Jewish voters and donors disenchanted with Obama's policies toward Israel would sidle up to the GOP's presidential nominee, Clinton supporters like Klein tout her long track record of support for Israel and the deep ties she enjoys with the Jewish community.
"A lot of what Hillary needs to do is just go back and remind people what her positions (on Israel) have been," he added.
But Jeff Berkowitz, a Republican operative who served as White House liaison to the Jewish community under President George W. Bush, was more skeptical of her ability to win over Jewish voters after eight years of Obama in the White House.
He said he believes Clinton's involvement in the Obama administration's fraught relationship with Israel will continue to loom large over her campaign.
"I think it will be very clear to those who care about the future of the U.S.-Israel relationship and the security of the Middle East that you need a very big change in direction from the Obama administration, and she was a big part of that direction," he said. "And making nice at the White House now isn't going to change that."
Republican criticism of Clinton goes beyond Israel to her backing of the Iran deal, which concerns many Jews who are Democrats as well -- though large numbers of Jews have also been supportive of the agreement.
Following her endorsement of the deal after it was reached, Clinton emphasized the need for a robust plan to counter growing Iranian influence and behavior in an increasingly destabilized region.
"We need to be clear-eyed about what we can expect from Iran," she said during a September speech at the Brookings Institution. "This isn't the start of some larger diplomatic opening. And we shouldn't expect that this deal will lead to a broader change in their behavior."
She added, "My approach will be distrust and verify."
Though policy differences on Iran, the peace process and other contentious issues would likely continue to complicate the U.S.-Israel relationship were Clinton to win the presidency, the former secretary of state is looking to emphasize points of agreement.
Eyeing an opportunity this week, Clinton penned an opinion piece Thursday in The Forward, a Jewish newspaper, titled, "How I Would Reaffirm Unbreakable Bond with Israel -- and Benjamin Netanyahu."
As Clinton is expected to do on the campaign trail, the Democratic presidential contender touts her personal connection to Israel -- dating back to her first visit in 1981 -- and her years of professional support for the Jewish state as a senator and as secretary of state.
"I have stood with Israel my entire career," Clinton wrote in The Forward. "As president, I will continue this fight."