In early June, the morning after he became the presumptive Democratic nominee, Barack Obama gave a speech focused squarely on the Middle East and Israel. While the timing was coincidental -- his appearance at the annual gathering of the American Israel Public Affairs Committee had been scheduled long before the primary race played out -- the speech was fitting, headed into the general election. U.S. dealings in the volatile region promise to remain at the center of the race, and the next presidency. On Israel in particular, Obama faces strategic challenges in his bid for the White House: He has had to combat long-running smear campaigns painting him as anti-Israel, while his Republican opponent, John McCain, has mobilized powerful conservative allies of Israel against him, including Senator Joe Lieberman.

"Jerusalem will remain the capital of Israel," Obama told the AIPAC crowd on June 4, "and it must remain undivided." He aimed to show his unequivocal support for Israel, and his remarks were received enthusiastically by the approximately 7,000 attendees at the powerful lobbying group's event. But they also produced political blowback, including among Obama's own dovish supporters, demonstrating just how thorny of an issue America's relationship with Israel remains. Even the State Department sounded wary of Obama's comments on Jerusalem, with a spokesman stating that the matter must ultimately be left up to the two sides in the conflict to resolve. In an interview with CNN the day after the speech, Obama reframed the issue in softer terms; inevitably, this led to accusations of flip-flopping and insincerity.

Obama's views on Israel's security, and the intractable conflict with the Palestinians, have met with uncertainty among some potentially key groups of voters -- namely older Jewish Americans, as well as some Evangelical Christians and other foreign policy hard-liners. There are sizable Jewish populations in important swing states such as Pennsylvania and Ohio, where there are also significant numbers of Evangelical supporters of Israel. With about three-quarters of a million Jews, though, Florida is the crucible when it comes to Israel, assuming the state will once again see a close contest in 2008. It has the third largest Jewish population in the country, and politically important southern Florida has one of the highest concentrations of Jews anywhere outside of Israel -- many of them senior citizens. According to a recent report in the New York Times, half of the Jewish population in Broward County is over age 59, and half of the Jews in Palm Beach County are over 70.

The vast majority of American Jews don't cast their votes based on considerations for Israel. Historically, they vote mostly on domestic issues, and they vote consistently and overwhelmingly Democratic. Obama has the support of many younger Jewish voters, amid strong support from youth voters in general, around the country. It is widely believed in political circles, however, that older Jewish voters in particular can be influenced to vote on the Israel issue -- if they are motivated by fear or uncertainty.

It is especially with this demographic that there is a danger to Obama in the oft-repeated accusation that his thinking is murky on the Israeli-Palestinian conflict, and on Israel's security situation vis-à-vis Iran. The doubts among some voters seem to have risen at least in part from legitimate concerns: the young senator's relative lack of a voting record in the Senate on Israel-related matters, and what some see as a confusing message from Obama more broadly on the region. As one influential Middle East activist and Obama supporter recently told me, "Looking at it objectively, I'd say he sends mixed signals. One day he talks about meeting with Ahmadinejad. Then he recites the AIPAC talking points."

But perhaps far more important, the doubts about Obama have been expanded and exacerbated for dubious reasons -- including attacks by his political opponents, and smear campaigns that were first launched against Obama via the Internet many months ago.

Whatever the cause, the Obama campaign is taking the issue very seriously, as demonstrated by his AIPAC appearance and recent media efforts focused on highlighting his personal and policy views on Israel. (Hillary Clinton's own comments before AIPAC the same day also reflected the issue's importance; she had yet to concede the race, but her speech included her first powerful gesture of support for Obama as the presumptive nominee: "I know Senator Obama will be a good friend to Israel," she said emphatically, to a constituency that has long viewed her as a steadfast ally.) In late June, the Obama campaign announced an upcoming trip abroad that will include a visit to Israel.

Representatives of AIPAC have affirmed repeatedly that they view Obama as a staunch friend of Israel, and that they would be comfortable with either him or John McCain as president.

Jeff Ballabon, a political strategist known as the architect of the 2004 Bush campaign's outreach to orthodox Jews, describes an intriguing strategic battle taking shape. According to Ballabon, because McCain's support from Evangelicals and the traditional conservative base of the Republican Party remains weak, McCain will have to use Israel to rally this crucial demographic in key battlegrounds like Florida. But if influential Jewish groups such as AIPAC continue to give their blessing to Obama, he says, Evangelicals and other worried supporters of Israel may take that as a sign that they don't need to back McCain.

If this logic is sound, the McCain campaign either has to more aggressively paint Obama as detrimental to Israel's security, or at least foster an impression of uncertainty as to how Obama would handle the Middle East.

That's where Joe Lieberman comes in.

After Obama's controversial remarks about Jerusalem, McCain himself said in a press conference, "I can't react to every comment that Senator Obama makes, because it probably will change as it did on sitting down and talking unconditionally with Ahmadinejad and other dictators." But it is Lieberman, a key surrogate for McCain, who has great sway on the topic. The hawkish Lieberman is tremendously popular among AIPAC's membership, Evangelical supporters of Israel, and Florida's Jewish retiree population. As one of America's most high-profile Jewish politicians, who broke new ground as the first Jewish vice presidential nominee in 2000, Lieberman carries much weight.

One of his roles in the McCain campaign clearly is to raise doubts about Obama regarding Israel and the Middle East. "I appreciate many of the very good intentions toward Israel that Senator Obama expressed today," Lieberman told reporters in a conference call following Obama's appearance before AIPAC, "but I also thought, respectfully, that there was a disconnect between what he said today, particularly in regard to Iran, and things he has said and done earlier."

In March, Lieberman accompanied McCain on a trip to Israel, a fact McCain highlighted in his own speech at the AIPAC convention. More recently, Lieberman launched an initiative called "Citizens for McCain," whose goal is to lure centrist Democratic voters into the McCain camp. A key focus for the group is foreign policy, and it has reportedly helped to attract Jewish Democratic donors to McCain. Although Lieberman is not a Republican, he also has offered to speak at the Republican National Convention at the end of the summer, a key moment for McCain to present his case for the White House to the national electorate.

Obama has his own high-profile Jewish lawmaker fighting on the front lines. Florida congressman Robert Wexler, who is co-chairman of Obama's campaign there, has been stumping for Obama in key areas of the state and working to counter the sway of Lieberman. He has been appealing in particular to older Jewish voters who, according to a recent article in the Miami Herald, see Wexler "more like a son than a congressman." In late May, Wexler brought Obama to speak at the synagogue in Boca Raton where he got married.

Looking ahead to November, Wexler told Salon in a phone interview that Obama's "steadfast and unequivocal support for Israel will be a major issue for Senator Obama in Florida and throughout the country, because it's a primary plank of his foreign policy."

Views on Obama and the Middle East continue to cut sharply in both directions, depending on who you talk to. Gidon Remba, president of an advocacy organization now sponsoring an initiative called "Jews for Obama" -- which is not affiliated with the Obama campaign -- says the idea that Obama has been vague on Israel is simply "what those who are trying to sow fear and doubt about Obama want the American Jewish community to believe." According to Remba, Obama has been "crystal clear" on the Middle East. "Obama would provide full economic, political, and diplomatic support for Israel, and stand by Israel's right to self-defense," Remba said. "But he would also clear a layer of rot that President Bush has dressed up in a way that appeals to some in the Jewish community. Sometimes a military policy is the worst thing for U.S. national security or Israel's security. We learned that in Iraq, and Israel learned that in Lebanon."

A political strategist close to the Obama campaign offered a similar view. On the Israeli-Palestinian conflict in particular, he told Salon that Obama "has every intention, from the beginning of his presidency, of making a concerted effort to help Israelis and Palestinians reach an agreement. This requires early commitment, and a sustained top-level diplomatic team working regularly both in the region and in Washington."

From the other end of the political spectrum, Jeff Ballabon agrees about the clarity, at least, of Obama's views on Middle East policy. He calls them "fantastically obvious." Obama would push the Israeli government to make concessions, he said, adding that "Israel is under enough pressure as it is, and doesn't need more from its best friend."

The particularly incendiary issue of whether to share Jerusalem, as well as the question of how best to deal with a rising Iran, are central to the debate. Jeremy Ben-Ami, executive director of J-Street, a new, dovish lobbying group in Washington, said that Obama's comment about an undivided Jerusalem at AIPAC was "distinctly unhelpful." "There has got to be a way to share the city," he said, "and an American president's role has to be to facilitate discussion between the parties, rather than have a foregone conclusion." (Ben-Ami said he was pleased when the Obama campaign softened its position on the Jerusalem issue.)

On the Iran front, J-Street applauds Obama's emphasis on diplomacy. "From day one," Ben-Ami says, "the next president has to send a completely different set of signals to Iran and the rest of the world. He has to put some carrots on the table, making it a carrot and stick approach."

In a tidy inversion of the Bush-McCain doctrine for Iran, the political strategist close to the Obama campaign said that Obama would "not tie his hands by taking certain tools that we have at our disposal off the table -- including diplomacy." He said that Obama would be willing "to meet with Iran at a time of his choosing," and, in addition to stating U.S. requirements, would offer the Iranians real incentives for their cooperation.

Ballabon's response is that "Obama's whole approach to Iran seems absolutely vapid and clueless. America doesn't need a touchy-feely leader."

The efforts by the McCain campaign and its surrogates to discredit Obama on the Middle East have been bolstered by the continuing smear campaigns directed against Obama by shadowy right-wing activists. (There is no evidence that these operatives are in any way connected with the McCain campaign.) The libelous emails, some of which even attempt to link Obama with Islamic terrorists, have spread virally since he emerged as a viable presidential candidate in 2007. By some accounts they have been targeted specifically at the American Jewish community using organized e-mail lists, although those rumors have not been proven.

Anecdotal evidence suggests that the e-mails have had an effect -- especially among the older Jewish voters in Florida who could end up being influential in a close contest. "There was no other evidence, so I believed the e-mails," Elizabeth Sadwith, a 90-year-old Jewish Floridian told the New York Times recently, adding that even though her children had assured her that the e-mails contained misinformation, "I still have doubts about him."

Both the Obama campaign and the unaffiliated Jews for Obama have rolled out websites to counter the smear campaign by rebutting assertions made in the e-mails. Jews for Obama is even planning to send Orthodox Jewish supporters of Obama to Florida to go door to door and persuade their co-religionists that the candidate would serve their interests.

The libelous attacks are unlikely to stop. "We're seeing as many smears every day as before," Remba, of Jews for Obama, says. "I fully expect that it will continue as quickly as whoever is coming up with them dishes them out."

"The right wing never gets exhausted of smear campaigns," agrees J-Street's Ben-Ami. "They would be falling down on their job if they did."

The net effect of widespread efforts to tarnish Obama's reputation in the eyes of pro-Israel voters -- and how important these voters actually will be in the overall electoral results -- will only be fully known in November. What is clear already, though, is that both campaigns, as well as their surrogates and proxies, are treating the Israel issue with great seriousness. They can't afford not to.