The Obama administration pursued secret communications with elements of Syria’s regime over several years in a failed attempt to limit violence and get President Bashar al-Assad to relinquish power, according to U.S. and Arab officials.
Early on, the U.S. looked for cracks in the regime it could exploit to encourage a military coup, but found few.
The efforts reflect how President Barack Obama’s administration has grappled to understand and interact with an opaque Middle East dictatorship run for 45 years by the Assad family.
Unlike the secret White House back channel to Iran, however, the Syria effort never gained momentum and communication was limited. This account is based on interviews with more than two dozen people, including current and former U.S. officials, Arab officials and diplomats. Most of these contacts haven’t been previously reported.
U.S. officials said communications with the regime came in fits and starts and were focused on specific issues. At times, senior officials spoke directly to each other and at others, they sent messages through intermediaries such as Mr. Assad’s main allies Russia and Iran.
Mr. Assad tried at different times to reach out to the administration to say the U.S. should unite with him to fight terrorism.
In 2011, as the regime began to crack down on protests and soldiers began to peel away from the army, U.S. intelligence officials identified officers from Mr. Assad’s minority Alawite sect who potentially could lead a regime change, according to former U.S. officials and current European officials.
“The White House’s policy in 2011 was to get to the point of a transition in Syria by finding cracks in the regime and offering incentives for people to abandon Assad,” a former senior administration official said.
But regime cohesiveness held, and the crackdown continued.
In August 2011, Mr. Obama publicly called for Mr. Assad to step down.
The administration’s core message never strayedfrom the U.S. line that Mr. Assad ultimately has to step down. But instead of persuading Mr. Assad to exit, the covert communications may have fed his sense of legitimacy and impunity.
That helped fuel the current wrangling among world powers over the Syrian leader’s future in any settlement. It also hampered the effort to consolidate the international fight against Islamic State.
“We have had times where we’ve said: ‘You could create a better environment for cease-fires if you stop dropping barrel bombs,’ ” a senior U.S. official said. “There’s communicating on specific issues,” the official added. “It’s not like Cuba or Iran, where we thought that we would essentially, in a secret bilateral negotiation, resolve the issue.”
Questions sent to the office of Assad adviser Bouthaina Shaaban about communication with the Obama administration were unanswered.
Throughout the conflict, two core elements of the administration’s Syria strategy—political and military pressure on the Assad regime—often hit a wall, forcing repeated shifts in tactics.
“This is a regime that is very supple politically. They’re very smart,” said Robert Ford, former U.S. ambassador to Damascus. “They’re always testing for weaknesses and pushing the envelope.”
By the summer of 2012, the White House strategy of orchestrating regime change had failed. The U.S. moved to support the rebels, but the effort ramped up too slowly.
“Russia doubled down and Iran doubled down, and it didn’t really have an effect,” a former administration official said.
In the summer of 2012, the administration sent warnings, through Russian and Iranian officials, to Mr. Assad not to use chemical weapons on a large scale, U.S. officials have said.
U.S. officials also talked to Syrian counterparts directly. Deputy Secretary of State William Burns, who retired last year, made two phone calls to Syrian foreign minister Walid al-Moallem to relay the warnings, U.S. officials said.
Fearing Mr. Assad would still escalate, Mr. Obama drew a public red line on chemical weapons in August 2012. Despite the warnings, sarin attacks in August 2013 killed an estimated 1,400 people. And while Mr. Obama threatened military action in response, he instead cut a deal with the regime to remove its chemical weapons stockpile.
For the next two years, Washington shifted its messaging to Damascus to focus on containing the conflict.
There was another reason to keep communication lines open: Five American citizens remain missing or in detention in Syria. Assistant Secretary of State Anne Patterson has talked with Syrian deputy foreign minister Faisal Mekdad at least twice about their fate.
The Obama administration later shifted gears back to diplomacy to get the Syrian government to the negotiating table.
At the center of that effort was a businessman and confidante of Mr. Assad, Khaled Ahmad, who has served as the Syrian leader’s main interlocutor in recent years with Western officials, including U.S. diplomats. Mr. Ahmad didn’t respond to questions sent by The Wall Street Journal.
“Assad was looking for ways to talk to the White House,” said Joshua Landis, a Syria expert and professor at the University of Oklahoma. Mr. Ahmad, a businessman from Homs province, was his point man.
In late 2013, the former ambassador to Damascus Mr. Ford—then a special administration envoy on Syria—met Mr. Ahmad in Geneva ahead of planned peace talks there. Mr. Ford told Mr. Ahmad the U.S. was still seeking a political transition away from Mr. Assad’s rule.
Mr. Ahmad countered that the U.S. and the West should help the Syrian government fight terrorism.
The rise of Islamic State in 2013 caught the U.S. administration off guard. Mr. Assad found in it a better opening to position himself as a partner in a fight against terror consuming the region, and rippling to the West.
By 2014, when the U.S. expanded airstrikes against the militants from Iraq to Syria, State Department officials were making phone calls to their counterparts at the Syrian foreign ministry to make sure Damascus steered clear of U.S. jets in Syrian skies, U.S. officials and others familiar the communications said.
Today, when Washington wants to notify Damascus where it is deploying U.S.-trained Syrian fighters to battle Islamic State so the fighters aren’t mistaken for rebels, Samantha Power, the U.S. envoy to the U.N., dispatches a deputy to talk to the Syrian envoy, Bashar Jaafari, these people said.
The White House says the notifications are not collaboration with the regime. But Mr. Assad has used them to his advantage.
“The regime was re-legitimized,” said Ibrahim Hamidi, a Syrian journalist who until 2013 ran the Damascus bureau for Al Hayat, a major pan-Arab newspaper. “Any communication with the U.S.—even the perception of it—gives them the upper hand.”
This spring, a former senior White House official, Steve Simon, met Mr. Assad in Damascus in a visit initiated and arranged by Mr. Ahmad.
Mr. Simon, who left the White House in 2014, had met Mr. Ahmad at least twice before the Damascus trip, which he portrayed to former colleagues and others as an individual initiative, not made on behalf of the government, according to several people familiar with the meetings.
Mr. Simon portrayed the trip to his former colleagues and others as an individual initiative, made in no formal administration capacity, in response to an invitation by Damascus, those familiar with the meetings said.
He notified former colleagues at the White House and State Department officials of his plans to meet the Syrian leader, these people said. He met former colleagues from the National Security Council, including senior director Robert Malley, before and after his meeting with Mr. Assad.
Mr. Simon outlined steps the regime could immediately take to generate goodwill with the international community: stop dropping barrel bombs; do more to fight Islamic State rather than antigovernment rebels; and cooperate with a United Nations-led effort for local cease-fires.
Mr. Assad responded with familiar talking points, focusing on his fight against terrorism. He showed some openness to local cease-fires on the government’s terms, two people familiar with the meeting said.
In the months that followed, a debate within the White House emerged on whether to redouble U.S. opposition to Mr. Assad or prioritize the Islamic State fight at the expense of the mission to go after the regime.
Write to Nour Malas at nour.malas@wsj.com and Carol E. Lee atcarol.lee@wsj.com