This article analyzes the conditions that might facilitate the long awaited diplomatic breakthrough in the relationship between Israel and the Palestinians in the Obama presidency. In order identify ten specific factors, the article relies on the rich historical record of peace negotiations, particularly since 1967. The analysis indicates that, despite the presence of a number of the factors which have facilitated past agreements, there are others which militate against excessive optimism. The arrival of Barack Obama's administration in Washington in January 2009 generated particularly intense speculation with regard the possibility of trying resolve the Israeli-Palestinian conflict once and for all. In the year before his inauguration, a number of veterans of the Oslo peace process of the 1990s wrote how to (or hownot- to) books in impatient anticipation of a dawn in Washington with regard the Israeli-Palestinian conflict, or even with regard the Middle East as a whole. Authors included Aaron David Miller, Daniel Kurtzer with Scott Lasensky, Martin Indyk, and Dennis Ross with David Makovsky.1 All of these books combined personal experience with policy prescriptions, and all made it clear that their authors fervently hoped that the new President would reverse George W. Bush's legacy. They joined a number of predecessors,2 who have not only described and analyzed the Arab-Israeli negotiations, but also have formulated a series of learned, lessons explicitly intended be relevant for future negotiations. The new wave of policy prescriptions was grounded on the general, even universal, perception that not only might Israeli-Palestinian peacemaking be galvanized by the new administration, but that this is a particularly crucial time for peacemaking in the Middle East in general (including, in addition the issue of Israel/Palestine, the issues of Iran, Lebanon, and the Golan Heights). For much of George W. Bush's term, most observers, both in the US and abroad, believed that as long as he was President, no long-term solution the Israeli-Palestinian conflict was likely, nor would a serious attempt be made achieve such a solution. In fact, the one exception proved the rule: very few considered the November 2007 Annapolis Conference be a serious effort.3 Most observers, of whatever political persuasion, perceived Bush as an unabashedly pro-Israel politician who rarely even tried portray himself as an honest broker between the sides. While Bush touted himself as the first US President openly advocate the two-state solution, few took this pronouncement very seriously. With two bloody wars within 30 months - Israel against Hizbullah in Lebanon (2006) and against Hamas in Gaza (2008-2009) - a new urgency for dealing with the conflict was established. The Arab League made clear rather forcefully that if Israel did not accept its Peace Initiative, announced in 2002 and reconfirmed in 2007, it would soon be withdrawn. And Arab leaders, who have warned repeatedly that the key dealing with the Arab and Muslim worlds in general must be a consensual settlement of the Israeli-Palestinian conflict, clearly expected action from Obama. These near-universal expectations of a break in the diplomatic stalemate were not unreasonable. Even apart from the current collection of crises, several characteristics of candidate Obama suggested that he would be strongly inclined make the resolution of the Israeli-Palestinian conflict a high priority on his agenda: a) he is in general a very engaged, resolute man, likely prove himself be an activist President; b) he appears approach virtually all issues in a comprehensive manner, looking for fundamental solutions; and c) during the presidential campaign of 2008 he spoke about the concerns of both parties the Middle East conflict - Israelis and Palestinians - with great passion, dwelling specifically on Israel's security concerns and on Palestinian suffering. …