Conservative websites have mocked the relationship as a Kerry-Assad “bromance,” seizing on comments the Senate Foreign Relations Committee chairman has made in speeches and during his six visits to Syria.

The politically tinged criticism of President Barack Obama’s nominee fails to capture the context of Kerry’swords, his more recent statements and what has been a complicated outreach to a mercurial and defiant leader. Both Republican and Democratic administrations also have struggled to fathom the Assad family, which has kept a tight grip on power for four decades and at times has cooperated with the West.

Syria supported the Persian Gulf War in 1991 to force Iraq out of Kuwait after President George H.W. Bush’s secretary of state, James A. Baker III, made a dozen trips to Damascus, the Syrian capital. Syria was an outcast for years and the U.S. pulled its ambassador in February 2005 after the assassination of Lebanon Prime Minister Rafik Hariri. Syria was widely accused of involvement in the killing, which Damascus has denied.

The nearly two-year civil war in Syria and the anger and frustration of some Republican lawmakers with Obama’s response is likely to produce several questions for Kerry. One of the newest committee members and a Kerry friend, Sen. John McCain, R-Ariz., has been the most vocal critic of Obama on Syria, complaining that the president’s policies have proved futile in stopping the bloodshed.

The United Nations recently estimated that at least 60,000 have been killed in the war and that millions have fled their homes.

The Massachusetts senator, tapped by Obama to replace Secretary of State Hillary Rodham Clinton, is on track for a smooth confirmation by his colleagues. His hearing could come as early as the week of Jan. 21.

Kerry summed up the uncertainty in the region when he said in a speech on March 16, 2011, that the “modern Middle East has long confounded American foreign-policy makers.”

The friend-or-foe conundrum for past administrations can be found in a series of photos.

There’s one of President Ronald Reagan’s envoy, Donald Rumsfeld, shaking hands with Iraqi leader Saddam Hussein in 1983, a decade before the United States and an international coalition went to war against him. In 2008, Secretary of State Condoleezza Rice sat down with Libyan leader Moammar Gadhafi, who three years later was killed by rebels backed by the United States.

Kerry’s observation came during an appearance before the Carnegie Endowment for International Peace in which he spoke optimistically about the Syrian government and the United States making progress with Assad.

“President Assad has been very generous with me in terms of the discussions we have had,” Kerry said. “And when I last went to — the last several trips to Syria — I asked President Assad to do certain things to build the relationship with the United States.”

Kerry ticked off six requests for Assad, including purchasing land for a U.S. Embassy in Damascus and border assistance with Iraq, and said the Syrian president fulfilled all of them.

“So my judgment is Syria will move; Syria will change, as it embraces a legitimate relationship with the United States and the West and economic opportunity that comes with it and the participation comes with it,” he said.

He was quick to add, “I take nothing at face value in any relationship.”

Toward the end of the same month, and after Sen. Richard Shelby, R-Ala., had led a congressional delegation to Syria, Clinton said that “many of the members of Congress of both parties who have gone to Syria in recent months have said they believe he’s (Assad) a reformer.”

Her remark was in the context of comparing Syria and Libya.

Officials for Kerry and Shelby say neither ever referred to Assad as a “reformer.”

A few days after Clinton’s remarks, Kerry said at a hearing on Syria that “violence against peaceful protesters is unacceptable” and took Assad to task for failing to promise significant reforms.

A month later, he backed Obama’s imposition of penalties against Syria and said “what is clear is that we need to increase the political and economic pressure so President Assad understands that he must end the violence and embrace reforms.”

In August, Kerry echoed Obama’s call for Assad to step aside.

The hard-line response was a clear reflection of the international outrage over Assad’s unceasing violence against his people. He stood in contrast to previous Kerry’s statements.

Shortly after Obama took office, Kerry traveled to Syria in February 2009 to push for Assad to honor Lebanon’s independence, to gain Syria’s help in getting Hezbollah to disarm and to make inroads in ending its close relationship with Iran. Kerry met with Assad and later said, “We are going to renew diplomacy but without any illusion, without any naivety, without any misplaced belief that, just by talking, things will automatically happen.”

In April 2010, Kerry met with Assad in Damascus and described Syria as “an essential player in bringing peace and stability to the region.”

Daniel Byman, a Georgetown University professor and a senior fellow at the Saban Center for Middle East Policy, said the criticism Kerry might face in the hearing “will be couched in ‘the administration is screwing this up, how will you fix it,’ rather than — my impression is Chuck Hagel’s (nomination to be defense secretary) will be much rougher. ‘You’re part of the problem, you’re not part of the solution.’ With Kerry, I think it’s going to be we’re delighted you’re coming to fix this problem.”