The stakes are high for President Obama heading into next week's U.N. General Assembly meeting in New York, as speculation mounts over a possible renewal of direct talks between the United States and Iran.
The meeting offers the White House a chance to make history by easing decades-long diplomatic tensions.
But it's a risky political maneuver for Obama. There's the matter of Iranian President Hassan Rouhani's recent deflection of a question about the Holocaust in an interview with NBC News, coupled with that nation's apparent effort to build a nuclear weapons arsenal.
Both are complicated issues on their own, and together risk undercutting his support among the American Jewish community, a core Democratic constituency. The president has a lot to gain, but also a lot to lose. Here's a guide to some of the issues facing Obama.
What kind of resistance would Obama face on easing sanctions with Iran?
The United States has enforced economic sanctions against Iran in some form or another since 1979's Iran Hostage Crisis, but they've intensified in recent years. They include restrictions on oil transactions, Iranian money transfers, and the assets of individuals or groups thought to be supporting terrorist organizations.
Easing these sanctions would be a hard sell for the president, but it could be necessary to pursue a diplomatic path.
"If we are going to make any progress with Iran, we will have to give up something, and that's what they're going to ask for," Sick said. "We're going to have to confront the question of whether we care more about a deal with Iran or about our pressure with sanctions."
But any move by Obama to ease the sanctions would face resistance from lawmakers.
According to Sen. Kelly Ayotte, R-N.H., a member of the Senate Armed Services Committee, "To ease up on sanctions without them taking credible action to stop their nuclear program that's leading toward nuclear weapons capability would be a big mistake."
Ayotte was one of 76 senators who sent a letter to Obama last month urging him "to bring a renewed sense of urgency" to dealing with the Iranian nuclear program.
The letter said "until we see a significant slowdown of Iran's nuclear activities, we believe our nation must toughen sanctions and reinforce the credibility of our option to use military force" at the same time as it explores diplomacy.
Among those signing the letter were the chairman of the Senate Foreign Relations Committee, Sen. Bob Menendez, D-N.J., and the third-ranking Senate Democratic leader, Sen. Charles Schumer, D-N.Y.
Would talks with Iran injure Obama's standing with supporters of Israel?
Obama has at times suffered from a tense relationship with the American Jewish community, a gap which Republicans have delighted at exploiting.
After Obama outlined his conditions for the peace process in Israel, his Republican challenger Mitt Romney accused the president of throwing Israel "under the bus."
That history forms the framework for any negotiations between the U.S. and Iran, the prospect of which the American Jewish community would meet with skepticism.
(Rouhani's refusal to definitively answer a question in his interview with NBC News' Ann Curry about his predecessor's denial of the Holocaust is particularly worrying, and the president also referred to Israel as a "warmongering" occupier.)
Even J Street, a moderate pro-Israel, pro-peace group which supports a diplomatic approach to addressing Iran's nuclear ambitions, regarded Rouhani's comments toward the Holocaust with a degree of skepticism.
"Any time a world leader denies or skirts questions about the horrors of the Holocaust, it's a huge warning flag for the Jewish community, as it is for the entire world," said Dylan Williams, who still encouraged Obama to pursue negotiations with Iran.
Other Jewish interest groups, like the influential American Israel Public Affairs Committee, says nothing has changed since Rouhani took power.
"While President Rouhani's rhetoric is more positive than his predecessor's, since his election there has been no change in the nation's nuclear program," the group said in a statement Friday.
“Congress and the Obama administration must continue to send a strong message that all options are on the table, and that the United States is prepared to use all instruments of American power to prevent Iran from acquiring a nuclear weapon capability.
"Still, Obama won't face another election, somewhat blunting this variable's impact. And despite Republicans' effort to make inroads with Jewish voters, Obama beat Romney handily among that community, 69 percent to 30 percent, last fall.
Are substantive face-to-face nuclear negotiations between Rouhani and Obama likely in New York?
An Obama-Rouhani meeting is "possible, but it has always been possible," according to White House spokesman Jay Carney.
"The extended hand has been there from the moment the president was sworn in."
That’s likely a reference to Obama’s first inaugural address, where he said, “to those who cling to power through corruption and deceit and the silencing of dissent, know that you are on the wrong side of history, but that we will extend a hand if you are willing to unclench your fist.”
But the United States has had little communication with Iranian leaders since 1979 when American diplomats were held as hostages in Tehran.
And Menendez said Thursday, “The president broke the ice in the letter (to Rouhani). I don’t think the president of the United States should be negotiating agreements. I think that’s a dangerous path and he should let his secretary of state and other counterparts be able to ultimately negotiate a process forward. But if he says ‘hello’ to him (Rouhani) and ‘I hope you’re actually going to move to action,’ that would probably be a good thing.”
What effect would Obama administration negotiations with Iran have on U.S. relations with other countries?
It’s difficult to assess the impact until we see if the negotiations might lead to a real agreement. Iran’s traditional adversaries, the Gulf states, Saudi Arabia, and Israel, will be watching any U.S.-Iran talks with nervousness, fearing any outcome that would strengthen the Iranian regime and its regional influence.
What effect might Obama’s handling of Syria have on negotiations with Rouhani?
Obama said in an interview last week that Iranian cooperation in Syria could help bring about a peaceful settlement of the civil war in which Iran is backing President Bashar Assad.
But in light of Obama’s threat to use force against Assad but then not using it, and Congress’s unwillingness to support an attack on Syria, some members of Congress are worried the Iranians might mistakenly think that Obama would shy away from using force to stop Iran from building nuclear weapons.
“I think it’s important that the Iranians not look at Syria and the process we went through there and assume that that is in any way reflective of what would be the congressional mindset or the U.S. mindset if we believe at some point they have the capacity to produce a nuclear weapon,” said Sen. Roy Blunt, R-Mo., a member of the Senate Armed Services Committee on Thursday.
Would Rouhani be a real negotiating partner for Obama?
Ken Pollack, a former CIA analyst and Middle East expert who served on the National Security Council staff under President Bill Clinton, said Monday, “I think Rouhani is the real deal, I think he wants a real deal with us.”
But he cautioned, “I don’t know whether Rouhani is going to be able to convince the Supreme Leader (Ayatollah Ali Khameni) to accept the deal that the United States would find acceptable, that the rest of the international community would find acceptable.”
He added, “We’ve got domestic politics on both sides that are going to make it very hard for us to consummate a deal.”
How has Rouhani changed the equation for Obama?
Rouhani has recently led a public relations offensive to put a less threatening image before the world than that of his often inflammatory predecessor, Mahmoud Ahmadinejad, who once said that Israel must be wiped off the map.
In an op-ed essay in the Washington Post on Friday, Rouhani called for “engaging with one’s counterparts, on the basis of equal footing and mutual respect” and defended what he called his country’s “peaceful nuclear energy program” which he said was aimed at “diversifying our energy resources.”
The Obama administration is clearly listening, but as Secretary of State John Kerry cautioned, “Rouhani's comments have been very positive, but everything needs to be put to the test.”
“Rouhani and Zarif are going to send a message that will be very different,” Columbia University Iran expert Gary Sick said in an interview with the Council on Foreign Relations. “I suspect that there will be little or no mention of Israel whatsoever in Rouhani's speech” to the UN General Assembly.
In addition, the trade sanctions which the United States and other nations imposed on Iran in response to its nuclear program are putting real pressure on the Iranian leaders.
According to Johns Hopkins University economist Steve Hanke, an expert on inflation and head of the Troubled Currencies Project at the Cato Institute, Iran’s annual inflation rate is now approaching 40 percent, one of the highest in the world.
This gives Rouhani an incentive to try to strike a deal that would lift the sanctions, at least partially. And it gives Obama an opportunity to engage diplomatically.