As President Barack Obama unveils his strategy to “degrade and destroy” the self-declared Islamic State, he will hope to capitalize upon widespread disgust in the Middle East against the group’s brutal ways.

But Mr. Obama also faces a daunting challenge in selling his plans for a regional coalition to leaders skeptical of White House readiness to follow through on his latest promises on Syria and Iraq.

The president is reportedly ready to expand into Syria the US military airstrikes that since last month have helped stop the advance of Sunni militants in Iraq. But analysts say the US track record of lukewarm and mutable engagement in Syria’s civil war has unsettled allies like Turkey, Jordan, Qatar, and Saudi Arabia, which all oppose Syrian President Bashar al-Assad.

“When you speak to senior decision makers in Riyadh, in Amman, it is shocking how deep their mistrust and disillusionment of the Obama administration is,” says Prof. Toby Dodge, director of the Middle East Center at the London School of Economics.

Moreover, these countries have favored, in various ways, the same anti-Assad rebels that Washington would like to prevail, but also the Islamists that spawned the Islamic State (IS) and other jihadi groups that are now beyond their control. That complicates any US-led coalition against radicalism.

Regional players note how Obama declared President Assad “must go” but did little to make it happen, with on-and-off-again support for “moderate” anti-Assad rebels.

And they point especially to August last year, when the US president failed to enforce his own explicit red line after Mr. Assad’s units used chemical weapons against civilians. Instead, a deal was brokered to remove and destroy Syria’s chemical weapons arsenal, but at the expense – in the perceptions of Middle East capitals, at least – of US credibility.

That makes Obama’s coalition-building challenge as tricky as any orchestrated by his predecessors in the past quarter-century, since President George H.W. Bush spent months lobbying regional leaders – even getting Syrian troops into the mix – to oust Saddam Hussein’s forces from Kuwait in 1990-1991.

“Collectively the whole of the Arab Middle East is a region coming to terms and reacting to what they feel to be an absent hegemon,” says Prof. Dodge. “Now our friends in the White House and Democrats everywhere will leap forward and say, ‘No, no, we’re not absent. We’re just avoiding the mistakes of Bush II, we’ve got a war-weary population.’ But in all my years traveling to the region, I have not seen a series of supposed allies of Washington so uneasy.”

Diplomatic outreach

While Obama is making his prime-time address tonight, the diplomatic outreach is already under way. US Secretary of State John Kerry arrived yesterday in Baghdad, where a new government was formed Monday night after the departure of former Prime Minister Nouri al-Maliki, whose Shiite-first policies did much to alienate Iraq’s Sunni tribes, who as a result partly backed the IS advance. IS was formerly known as ISIS; US officials often refer to ISIL, an alternative acronym.

Mr. Kerry will be in Jordan today, and in Riyadh tomorrow will convene a regional security meeting aimed at marshaling coalition partners.

While Washington’s Arab allies would likely welcome an expansion of the US bombing campaign to Syria, their agenda may be more about regime change in Damascus than disrupting the IS’s reign in the badlands of northeast Syria.

“If there is a sense that the fight against ISIS in Syria is being seen in isolation from the bigger need, or the equal need, to have change in Syria from Assad, then I think we will start to see this coalition really start to fray,” says Salman Shaikh, director of the Brookings Doha Center in Qatar.

While that may be a secondary goal for the White House, many in any anti-IS coalition will want to see the US apply the same resolve to Syria’s regime that it has applied to Iraq and its fight against IS.

“There is really a lot of residual anger towards the United States and its motivations in Syria over the last three years – first and foremost among Syrians on the ground,” says Mr. Shaikh. “There is a danger that if people are asked to choose, especially on the ground in Syria, they might decide, ‘Well, we’re not going to fight [IS] and leave Assad alone, we’d rather walk away.’”

Risk of backlash

As successive US presidents have discovered, military interventions in Arab lands, even on the back of regional coalitions, are fraught with political risks and can quickly generate violent reactions.

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That’s why certain players like Qatar and Saudi Arabia are likely to hedge their bets to see how the US manages the coalition and its own objectives. A division of labor could emerge such that Arab members provide logistical and other support, but stop far short of the active military roles some like Qatar played in Libya to bring down Qaddafi in 2011.

In 2003, President George W. Bush’s “coalition of the willing” for the Iraq invasion was often mocked for the number of token deployments meant to provide political cover and little else. “Kerry [may] have a kind of Colin Powell-style-like grand coalition in mind, but I don’t think he’s selling much,” says Dodge.