Candidate Obama pledged that his Middle East policy would include re-engagement with Syria; President Obama will find that the past is not easily overcome. The reasons behind his vow remain pertinent. Syria holds important cards in Lebanon, Iraq and Palestine, is Iran’s most important Arab ally and has substantial influence over Hamas and Hizbollah. There are indications of potential common ground on which to build, from resuming Israeli-Syrian negotiations, to consolidating progress in Iraq to blunting the rise of jihadi militancy and sectarianism. But significant obstacles to healthy, mutually beneficial relations remain, along with a legacy of estrangement and distrust. They dictate the need for a prudent approach that seeks first to rebuild ties and restore confidence. It will be critical to reassure Damascus that the U.S. is interested in improving relations and resolving the Israeli-Arab conflict, not in regime change. It is also equally critical not to compromise on core principles such as Lebanon’s sovereignty or the integrity of the international tribunal investigating the assassination of former Prime Minister Rafiq Hariri.

President Bush’s policy was premised on the belief that isolation and pressure would lead to substantial changes in Syrian behaviour. It failed on both counts. The policy crumbled, and the sought-after behavioural changes never truly materialised. Awareness of this outcome, coupled with Senator Obama’s own conviction that engagement – far from being a sign of weakness – was the mark of diplomatic strength, formed the backdrop to his campaign pledge and is likely to inform his presidential policy. The question no longer is whether to engage Syria but how.

That is where the hard part begins, for engagement is easier said than done. Although the open hostility witnessed under the Bush administration was an anomaly in U.S.-Syrian relations, the ordinary state of affairs hardly has been the reverse. Even prior to the Bush presidency, whether under President Clinton or his predecessors, the relationship had been problematic, marked by disagreement as much as dialogue. From Washington’s perspective, Syria continued to support militant Palestinian and Lebanese groups; from Damascus’s, the U.S. continued to harbour a regional agenda inconsistent with its own aspirations and interests. In short, while breaking with the Bush legacy is part of the solution, simply reverting to what preceded it is not.

Nor, even if it were advisable, would it be possible to rewind the tape. The last eight years have left their imprint in several, at times indelible ways. The legacy is threefold. First is the web of legal or administrative measures aimed at Syria. These include an array of binding UN Security Council resolutions related to Damascus’s role in Lebanon, the establishment of the international tribunal regarding the Hariri assassination and an assortment of U.S. economic sanctions. They undoubtedly will continue to shape U.S.-Syrian relations; for the most part, their relaxation will occur, if at all, as a by-product of improved relations rather than as a means of achieving them.

Secondly, U.S. policy has deepened estrangement between the two countries. As Washington recalled its ambassador, downgraded its representation in Damascus and shunned routine encounters with Syrian representatives, Damascus responded by boycotting what remained of the U.S. embassy. Syria has undergone significant change since the U.S. last had sustained interaction. It will take time for policy-makers to come to terms with transformations in the regime’s governance style, power structure, threat perceptions, regional positioning and socio-economic constraints. A policy shift will be all the more difficult to undertake as these years coincided with a hardening of public and congressional attitudes toward Syria that inevitably will influence the new team. Most of the president’s advisers, although in favour of a policy of engagement, bore witness to Syrian action in Iraq and Lebanon, are sceptical about the nature of the regime, question prospects for a genuine shift in its regional posture and sense that Damascus is more likely to move when ignored than when courted.

A third constraint stems from changes in the regional landscape. The Iraq invasion fuelled sectarian tensions and boosted Iran’s influence; neglect and mismanagement of the Arab-Israeli conflict bolstered Palestinian and other rejectionists; Lebanon’s polarisation and the 2006 war enhanced Hizbollah’s influence; attempts to isolate Syria strengthened its ties to Iran; jihadi militancy is on the rise; and the Arab world is as divided as ever. The net result will be to complicate any putative Syrian strategic repositioning.

But there are promising signs, too. For several reasons – most having little or nothing to do with the U.S. – Damascus appears to be softening its posture on Iraq and Lebanon, undertaking at least some effort to control its border with the former while establishing diplomatic relations with the latter. Talks with Israel, although halted due to the war in Gaza and the elections in Israel, might well resume with U.S. participation. Relations with Turkey have become a central element of Syrian foreign policy, offsetting Iran’s exclusive influence and providing Ankara with real leverage. Signs of unease already can be detected in Syrian-Iranian relations; with patience and deft management, they might be substantially transformed.

How the two sides first engage one another will be critical; mistakes, miscalculations or mismatched expectations could do significant damage. In this, the second of three companion reports, Crisis Group examines in greater depth the last eight years’ legacy, drawing lessons for the new administration’s Syria policy. It concludes that, in order to pave the way for a more fruitful relationship, the U.S. early on should take the following steps:

• Clearly articulate a set of guiding core principles, including:

­– support for and participation in renewed peace negotiations on all tracks;

– consistent with past Israeli-Syrian negotiations, any final agreement should entail full Israeli withdrawal from the Golan Heights, firm security arrangements and the establishment of normal, peaceful bilateral relations;

– no arrangement or compromise over the international tribunal or Lebanon’s sovereignty;

– respect for such international norms should not be read as a desire to destabilise or change Syria’s regime; and

– open acknowledgment of positive Syrian measures.

• Set in place effective channels of communication, by:

– nominating an ambassador;

– requesting that Syria treat U.S. diplomats respectfully and doing likewise with Syrian diplomats posted in the U.S.;

– establishing a privileged, personal and direct channel between President Obama and President Assad, possible through Middle East Peace Envoy George Mitchell; and

– conducting a relatively early visit by a high-level U.S. military official in order to establish U.S.-Syrian-Iraqi security cooperation.

• Carefully rethink sanctions in line with clear policy objectives, streamline licensing procedures and loosen restrictions on humanitarian or public safety grounds, such as for medical items or civil aviation-related goods to help replace an ageing and dangerous national fleet.

The initial briefing in this series described lessons from the French experience at re-engagement with Syria. The third and final report will consider evolutions on the Syrian side and propose broader policy recommendations for Washington and Damascus.

Damascus/Washington/Brussels, 11 February 2009