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Security forces loyal to Syrian leader Bashar al-Assad pressed a sustained assault against protesters Thursday in one of the bloodiest episodes in the so-called Arab Spring, exposing the quandary that President Barack Obama faces in trying to deal with a man he once thought he could convert into an ally.

The killing of at least 70 people around the central town of Homs in the past five days, according to activists, brought to an estimated 1,100 the total toll in Mr. Assad's months-long crackdown and sparked tougher condemnation from the Obama administration. Secretary of State Hillary Clinton urged other Arab states, Russia and China to join in protesting the violence.

But the Obama administration still wasn't quite ready to give up on Mr. Assad.

"The legitimacy that is necessary for anyone to expect change to occur under this current government is, if not gone, nearly run out," Mrs. Clinton told reporters. "If he's not going to lead the reform, he needs to get out of the way."

Mrs. Clinton's ambiguity highlights the frustrating U.S. courtship of Bashar al-Assad. For more than two years, Mr. Obama's foreign-policy team has tried to woo Mr. Assad away from America's regional nemesis, Iran, and persuade him to resume peace talks with America's regional friend, Israel. For more than two years, Mr. Assad has frustrated the U.S. with the promise of reform and the practice of repression.

At one point Sen. John Kerry, the president's informal envoy to Mr. Assad, even secretly negotiated an agreement with the Syrians to restart peace talks with Israel, according to people briefed on the matter. Having harbored such lofty aspirations, the Obama administration is finding it hard to cut loose the 45-year-old, London-trained ophthalmologist.

As democratic protests swept the Middle East and North Africa, Mr. Obama ushered Egyptian President Hosni Mubarak out the door and sent U.S. jets to try to topple Libyan leader Moammar Gadhafi. But so far nobody in the Obama administration has publicly urged Mr. Assad to surrender power.

Mr. Obama entered the Oval Office in 2009 determined to engage some of Washington's most intractable foes, including Iranian President Mahmoud Ahmadinejad and Venezuelan leader Hugo Chavez. But many of Mr. Obama's foreign-affairs advisers saw Mr. Assad as the most promising target.

The Syrian president had suggested to U.S. officials a willingness to break his military alliance with Tehran, forge peace with Israel and diminish Syrian support for the militant groups Hezbollah and Hamas.

The White House put in place a foreign-policy team with vast experience dealing with Mr. Assad and his late father, President Hafez al-Assad. And in Mr. Kerry, chairman of the Senate Foreign Relations Committee, the White House found a key ally in pursuing Mr. Assad: In repeated trips to Damascus, the Massachusetts Democrat had established something approaching a friendship with Mr. Assad.

Mr. Obama quickly ran into opposition from lawmakers who argued that Mr. Assad was only feigning interest in U.S. outreach. Now they worry that the administration has waited too long to seek his ouster.

"One of the game-changers for the Middle East is the fall of Assad," says Sen. John McCain (R., Ariz.). "It's just baffling to me how it's not in the U.S.'s interest to seek the removal of Bashar Assad."

Senior U.S. officials say Washington's tempered response to the Syrian crackdown has been driven by fears that Mr. Assad's overthrow could unleash even wider sectarian violence. American allies in Turkey, Saudi Arabia and Israel have expressed similar fears. There's also a belief among some in the U.S. government that Mr. Assad will weather the current storm no matter what the U.S. does.

"He probably has the wherewithal to be sitting in the palace for quite some time," said a senior administration official.

U.S. relations with Syria were at a low when Mr. Obama took office pledging to re-engage Damascus. The George W. Bush administration had accused Mr. Assad of facilitating the flow of al Qaeda fighters into Iraq and secretly pursuing nuclear weapons in cahoots with North Korea.

President Obama's early signals were mixed. In March of 2009, Messrs. Kerry and Assad and their wives dined together in the ancient heart of Damascus, just down the street from where the head of John the Baptist is thought to be entombed. For hours the men talked bilateral relations and Mideast peace, forging a strong working relationship, according to Syrian officials and congressional aides. Mr. Kerry says he acted independently but coordinated the visit with the White House.

The mood quickly soured. In May 2009, Mr. Obama renewed extensive White House sanctions on the Syrian regime, citing its support for militant groups. A few days earlier, a White House mission to Damascus failed to secure better Syrian cooperation in policing the Iraqi border.

It took an intervention by Mr. Kerry to help revive the engagement. Mr. Kerry organized a phone call between Mrs. Clinton and her Syrian counterpart, Walid Moallem. That led to a higher-level visit to Damascus later in the year, headed by George Mitchell, then the special Mideast envoy. The White House agreed to ease some sanctions. The Syrians promised to better police the Syrian-Iraq border.

The Obama administration and Mr. Kerry accelerated efforts in 2010 to woo Syria, according to officials. Mr. Mitchell's team had a detailed plan for ending the Israeli-Syrian dispute over the Golan Heights. A former U.S. army attaché in Beirut, Fred Hof, began making regular trips to Damascus on the administration's behalf.

Mr. Kerry, meanwhile, became Mr. Assad's champion in the U.S., urging lawmakers and policymakers to embrace the Syrian leader as a partner in stabilizing the Mideast. At a dinner in Washington in late 2009, Mr. Kerry described how the Syrian leader bemoaned the growing conservatism in his country. Mr. Assad's London-born wife, Asma, had to wear a head-scarf when visiting Damascus's historic Umayyad mosque, while his mother hadn't decades earlier, Mr. Kerry recounted Syria's leader saying.

"He doesn't want to lead a religious-based country," Mr. Kerry told the audience.

Some at the dinner, though, were Lebanese-Americans, who knew Damascus funded such Islamist organizations as Hezbollah and Hamas. "Kerry's characterization of Assad seemed grossly exaggerated," said one attendee at the dinner. "But the senator promoted it unchecked."

Some in the U.S. government also doubted this rosy view of Mr. Assad. Damascus continued to stonewall investigators from the U.N.'s nuclear watchdog, which suspected Syria of a covert program to produce plutonium for nuclear bombs. Mr. Assad showed no signs of weakening his alliance with Tehran. And U.S. intelligence services were alarmed to view satellite photos in early 2010 showing Syrian military units transferring long-range Scud missile systems to Hezbollah, which the U.S. designates a terrorist organization.

Sen. Kerry says he harbored no illusions about the Syrian president. "I never argued Assad was a reformer so far as the internal political affairs of Syria," he said in an interview. "But there was an opportunity staring us in the face on foreign affairs."

The White House dispatched Mr. Kerry back to Damascus in the spring of 2010 to confront Mr. Assad on the Scud issue, but Syria's dictator denied the charges. Secretary of State Clinton, while committed to engagement, complained to aides about Syrian duplicity, according to U.S. officials. She summoned Syrian diplomats to the State Department four times that spring to protest the alleged weapons shipments.

Nonetheless, Messrs. Kerry and Mitchell pressed ahead to restart peace talks. The Syrian leader stressed that reclaiming the Golan Heights from Israel, rather than advancing Iran's regional ambitions, remained his main foreign-policy objective.

"If I have everything I need as Syria, I cannot say no to the [peace] treaty," Mr. Assad said in January in an interview with The Wall Street Journal.

In the second half of last year, Mr. Kerry began shuttling between the Syrians and the Israelis, according to people briefed on the diplomacy. The senator believed the talks were progressing so well that last fall he and Mr. Assad's aides secretly drafted terms they hoped would allow for the resumption of direct Israeli-Syrian peace talks, according to people familiar with their work. The plan: Israelis would agree to resume talks and commit to returning all Syrian lands seized during the 1967 Six Day War. Mr. Assad would pledge to distance himself from Iran and Hezbollah.

"I thought what I brought back in writing was sufficiently powerful and real that it merited any administration to follow up on it," Mr. Kerry recalls.

This January, however, the U.S. diplomatic pursuit of Damascus began to fray. American officials and French President Nicolas Sarkozy had pressed Mr. Assad to help stabilize Lebanon. But that month, Hezbollah and Syria's other Lebanese allies engineered the ouster of Prime Minister Saad Hariri, a close Western ally.

Mr. Kerry was booked into Damascus's Four Seasons Hotel in anticipation of his seventh meeting with the Syrian leader. But days before the senator's trip, the White House and French government intervened to block the meeting, according to U.S. and European officials. They didn't want to give Syria's strongman the stamp of approval that a visit from the powerful senator would imply.

Neither the Obama administration nor Mr. Kerry appeared prepared for the political uprising that rocked Syria just weeks later. Many U.S. officials believed Syria's rulers had so repressed political dissent that the country wasn't susceptible to the type of people-power movement that overthrew Egyptian and Tunisian leaders.

Mr. Kerry gave an address on the Middle East on March 19 in Washington and again raised eyebrows by heaping praise on Mr. Assad. A few days later, Mrs. Clinton fueled even greater anger among Syrian human-rights activists by echoing Mr. Kerry's line that Mr. Assad might yet embrace reform.

The Obama administration has distanced itself from Mr. Assad as more protesters have fallen to the Assad regime's snipers and tanks in recent weeks. The White House has sanctioned Mr. Assad and many of his top advisers. And U.S. officials have acknowledged that the time for cutting a peace deal between Mr. Assad and Israel has probably passed.

Still, Syrian democracy activists, many of whom gathered in Turkey this week, voiced concern that Washington continues to cling to a hope that the Syrian leader could be rehabilitated.

"The problem here is that this policy of the U.S. still legitimates the position of Bashar al-Assad, and isn't commensurate with the position of the people demonstrating in the streets," said Ammar Abdulhamid, a Washington-based activist.
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