For someone who thinks of himself as an adroit dealmaker, the Middle East in general and Israel in particular, provides some of the most difficult ties to unknot in global affairs.
That's why it was not surprising that Donald Trump, author of the Art of the Deal and in his own estimation a skilled negotiator, jumped on the chance to insert himself into the minefield that is Middle Eastern politics.
So ahead of Trump's first presidential visit to Israel here's a look at two promises he made regarding Israel and the Middle East that he will now have to confront as well as a third unplanned topic, he will also have to deal with.
Trump's reported disclosure of secret intelligence
The reported divulging of classified information originating from Israel by President Trump in the White House during a high-profile visit by the Russian Foreign Minister and Moscow's US ambassador is unlikely to be on the official itinerary when Trump meets Prime Minister Benjamin Netanyahu.
Yet it would be unusual if this incident, which is extremely sensitive for both sides, would not somehow be broached during the presidential visit.
"I believe that the last affair regarding intelligence materials that were disclosed to third parties is going to affect the relationship a little bit because this is beyond the regular relationship of the two relationship communities and infringes the tradition in that field”, said Gilead Sher, who served as chief of staff for former Israeli Prime Minister and Defense Minister Ehud Barak.
That is why due to the sensitive nature of the issue it will "probably be discussed and cleared not in front of the cameras and not as part of the official visit, but behind closed doors between the leaders and I believe that it will be resolved eventually in a way that would be satisfactory to both parties," said Sher.
The US embassy question
Trump, during his campaign, repeatedly promised to relocate the US embassy in Israel from Tel Aviv to Jerusalem, which Israel considers its capital. Palestinians who also claim the city as a future capital of a Palestinian state oppose this, as do Jordan and other Arab states.
Since 1995, all American presidents have chosen to walk the same fine line on the issue after Congress passed a directive calling on the US to recognize Jerusalem as Israel's capital and move its embassy there. They have signed waivers delaying the relocation every six months for national security reasons.
And it looks like Trump will now join his predecessors and do the same.
"Most people think that the campaign promise to move the US embassy from Tel Aviv to Jerusalem has at a minimum been put on the back burner for now," said Michele Dunne, director of the Middle East program at the Carnegie Endowment for International Peace. "So that is unlikely to happen. But he could still say or do things that somehow recognize Jerusalem as Israel's capital."
The Israeli-Palestinian peace process
While Trump is expected to backtrack on his campaign vow to relocate the US embassy, he is not expected to shelve what was arguably his most audacious promise: to reach a peace deal between Israelis and Palestinians.
To the contrary, Trump earlier this month - during a White House meeting with Palestinian leader Mahmoud Abbas - appeared to double down on his pledge when he said in reference to a peace deal: "We will get done."
"Trump wants to announce or preside over the recommencement of peace talks between Israelis and Palestinians," said Josh Saidoff, fellow at the Center for Middle East Development at the University of California, Los Angeles (UCLA) via email.
Since his remarks during the Abbas visit and especially since it was announced that Trump would visit Israel during his first international trip as president less than four months after taking office - his predecessors Obama and Bush both visited Israel during their second term - there has been speculation about whether the president would use his Israel trip to officially re-launch the stalled US initiative to broker a peace deal between Israelis and Palestinians.
"From an Israeli perspective, if I see a process with a hands-on American presidential involvement starting at the end of this visit, I would say this would mark a success for all parties concerned," said Gilead Sher, who served as chief Israeli negotiator at the Camp David summit and the Taba peace talks with the Palestinians.
But Sher qualified that he would only regard a new US peace effort as serious if it went beyond a mere one-time meeting.
Asked whether he believes Trump is aware of the challenges of brokering a peace deal and capable to overcome them, Sher said he sincerely hopes so. "I think that President Trump is well positioned to facilitate a US-led effort towards that aim once the two state for two people solution is articulated in a way that is binding and continuous."
Carnegie's Middle East expert Michele Dunne is more skeptical: "There is no indication at this point that there is any kind of well-formed strategy or approach to the Middle East peace process. They are still in exploration mode."