in Cairo for a "new beginning" for America with the Muslim world.
In that seminal speech in 2009, Obama brimmed with ambition, telling hard truths to Arabs but also daringly conceded faults of US behavior.
He also promised to work for Israeli-Palestinian peace with "all the patience and dedication that the task requires."
On Wednesday, with a failed peace effort to show for his pains, Obama will arrive in Jerusalem on what experts see as a "maintenance trip" without a new peace initiative.
"My goal on this trip is to listen," Obama told Israeli television on Thursday, saying he wanted to hear ideas from Israeli Prime Minister Benjamin Netanyahu and Palestinian leaders Mahmud Abbas and Salam Fayyad.
Given his limited goals, questions are being asked as to why Obama is going at all, other than to check a political box after being criticized for not visiting key ally Israel in his first term.
But, by going now, Obama can bill the trip as a chance to reconnect on key challenges like Iran and Syria as he starts a second term and Netanyahu begins his new mandate.
Had he waited a year, questions about absent 'deliverables' would have been even more acute.
Obama may share frustration common to several of his predecessors: sources said he told Jewish community leaders privately last week he cannot want peace more than the parties themselves.
But conditions for a resumption of the "peace process" are hardly ripe, in Israel or the Palestinian territories and outside Middle Eastern powers may be too pre-occupied to play a useful role.
Egypt, under the Muslim Brotherhood, is more hostile to Israel, at least publicly, and is trying to keep a lid on its own internal turmoil.
Syria is imploding and in no shape to weigh in on mechanics of a regional peace. And Saudi Arabia, spooked by political uproar around its borders, has an ailing king and brewing succession intrigue.
While Obama's visit may be welcomed as a symbolic sign of engagement by his hosts, his regional audience will be less receptive than four years ago.
"I think the administration wasted three valuable years after Cairo," said Marwan Muasher, a former Jordanian foreign minister now with the Carnegie Endowment in Washington.
"They raised expectations to an unprecedented level, but then they didn't follow up."
What Obama could not have known in Cairo was that the region was on the cusp of monumental political change with unprecedented uprisings against autocratic rulers.
In 2009, Washington looked at Syrian President Bashar al-Assad, as a potential dialogue partner, Moamer Kadhafi still ruled Libya, and the United States had an ally in long-ruling autocrat Hosni Mubarak in Egypt.
Now Assad is a blood-soaked pariah, usurped Kadhafi died humiliated and Mubarak was toppled. Iran's nuclear drive, broiling political change and Syria's agony now preoccupy the region more than Arab-Israeli peace.
Obama has had to navigate the challenges of the Arab awakening which tore up a generation of US Middle East strategy, leaving Washington with less leverage.
"There are many dynamics and trends that are beyond the control of the United States or the influence of the United States or any other actor," said Haim Malka, of the Center for Strategic and International Studies.
Obama was also dealt a tough hand.
The idea of US military omnipotence was punctured as a myth when Washington got bogged down in Iraq - ironically Obama will visit the region 10 years after the invasion to oust Saddam Hussein.
There is also a perception in the region that US power projection is compromised by financial woes - reflected in the decision to postpone a Gulf deployment by the aircraft carrier USS Harry S Truman.
Obama's aides dispute the idea that subsequent events have devalued the Cairo speech or rendered it naive.
"Frankly, the Cairo speech lays out a framework that holds in terms of how the president views those issues," said Ben Rhodes, a US deputy national security advisor, while admitting Obama's vision is only partially fulfilled.
While Obama may have trimmed his sails in the Middle East, Israelis and Americans say the trip is a vital chance to consult on key security challenges.
And despite unpromising conditions, Obama has a key strategic interest in squeezing some confidence building measures out of Israelis and Palestinians, said Alan Elsner, vice president for communications at J Street, a US-based liberal peace advocacy group.
"The United States has little influence to effect events in Syria or Egypt and is trying to handle an upsurge of extremists in Yemen and Mali."
"The only place where it could inject more stability in the region is in the Arab-Israeli context."