Secretary of State Henry Kissinger’s first meeting with Syrian President Hafez al-Assad, in 1973, dragged on until almost eleven P.M. It ran so long, the Times reported, that the media began to speculate about whether America’s top diplomat had been kidnapped. Assad “negotiated tenaciously and daringly like a riverboat gambler to make sure he had exacted the last sliver of available concessions,” Kissinger recalled in his memoir, “Years of Upheaval.” The marathons were typical. In 1991, Secretary of State James Baker famously waved a white flag “in submission” after almost ten hours because he needed a bathroom break. Baker called negotiating with Assad “bladder diplomacy.”

Since the bloodless coup, in 1970, that brought the family to power, the Assad dynasty—the founding father, Hafez, and his heir and second son, Bashar—has exasperated nine American Presidents. “Time-consuming, nerve-racking, and bizarre,” Kissinger said of his sessions with Hafez al-Assad. Republican and Democratic Administrations alike have coaxed and cajoled, prodded and praised, and, most recently, confronted and condemned the Assads to induce policy changes.

Kissinger made twenty-eight trips to Damascus—fourteen in a single month—to deal with the fallout from the 1973 Arab-Israeli War. He finally brokered an agreement with Assad, in 1974, to disengage Syrian and Israeli troops along the Golan Heights. Less than a month later, Richard Nixon became the first President to visit Damascus. He received a twenty-one-gun salute and rode in an open car with Assad past hundreds of American flags flapping in a strong breeze. A sign along the route proclaimed, “Revolutionary Damascus welcomes President Nixon.” But neither Nixon, who was forced to resign two months later, nor Gerald Ford was able to channel that connection during Assad’s early years in power into a broader Middle East peace.

Assad means “lion,” and he played up his role as the “Lion of Damascus.” Syria had been weak and unstable after independence from France, in 1946. It witnessed twenty coups in twenty-one years. Assad’s was the last, in 1970. It was, initially, applauded. The Times reported, “Admirers of General Assad welcome his seizure of power within the ruling Baath Party as the predictable victory of pragmatism over ideology.” But, to strengthen the Syrian state and turn it into a regional power, Assad became increasingly ruthless with opponents at home and obstinate with the outside world.

Jimmy Carter met Assad in Geneva, in 1977, to explore prospects for a U.S.-Soviet conference on Middle East peace. Assad was unyielding. He demanded the return of territory seized by Israel and strategic parity for the Arab world. He was willing, Carter recalled, to “face serious political and military confrontations rather than yield on this principle.” Carter even invited the Syrian leader to visit Washington. The optics of a White House photo op did not entice Assad. “He replied that he had no interest ever to visit the United States,” Carter later wrote. A year later, when Carter brokered the Camp David Accords, between the Egyptian President, Anwar Sadat, and the Israeli Prime Minister, Menachem Begin, Assad countered by deepening ties to Moscow.

Assad repeatedly played the spoiler to peace during the Reagan Administration. In 1981, I covered the Arab League summit in Fez, Morocco, where Saudi Crown Prince Fahd was to present his eight-point plan, supported by Washington, to recognize Israel’s right to “live in peace” in exchange for the return of territory. Twenty-one delegations arrived in Fez and waited for Assad. I was at the airport when the Syrian plane carrying his bodyguards and staff arrived. Assad never showed. The summit collapsed.

Tensions between Reagan and Assad turned openly hostile after Israel’s 1982 invasion of Lebanon, where Syria had thousands of troops deployed. The Secretary of State, George Shultz, brokered a formal peace treaty between Israel and Lebanon, but Assad effectively torpedoed the deal by refusing to pull out his own forces—a condition for Israel’s withdrawal.

Assad played brazen strategic games to sustain Syrian leverage. During the Israeli invasion, he supported the deployment of Iranian Revolutionary Guards in Lebanon—and the creation of a new Shiite militia that grew into Hezbollah. It was blamed, in April, 1983, for the bombing of the U.S. Embassy in Beirut, the first suicide attack against an American target anywhere. It was followed by attacks on U.S. Marine peacekeepers deployed in Lebanon, where more than two hundred Navy personnel were killed, and on a second U.S. Embassy. The United States held Assad as responsible as Iran and Hezbollah for introducing a whole new genre of warfare. Thirty-five years later, Hezbollah is one of the most powerful militias in the Middle East. Tens of thousands of its fighters are now helping the Assad dynasty hold on to power.

“Assad did not hesitate to use violence or terrorism to further his ends,” Shultz later wrote, in “Turmoil and Triumph,” his memoir. Yet the Reagan Administration maintained diplomatic ties with Damascus—and contact with Assad. Shultz went back to Syria to see him during another bid for Middle East peace, in 1988. “I also knew that it was important to the other Arabs that I consult with him,” Shultz wrote. The outreach, again, proved futile. Asked by the travelling press whether he held out any hope, Shultz replied, “I’m overwhelmed by your sense of humor.”

Saddam Hussein’s invasion of Kuwait, in August, 1990, provided a rare intersection of interests between Washington and Damascus. Syria and Iraq were rivals, and Assad committed thousands of troops to the U.S.-led coalition for Operation Desert Storm to push Iraq out of oil-rich Kuwait. As part of his plan to forge a “new world order” after the Gulf War, President George H. W. Bush met Assad in Geneva and won his buy-in for a joint U.S.-Soviet peace conference in Madrid. But Assad did not attend; the momentum stalled.

The demise of the Soviet Union, in 1991, cost Assad his most important ally. The 1993 Oslo Accords, between Israel and the Palestinians, followed by the 1994 peace treaty between Jordan and Israel, also made him look like the odd man out in the region. President Clinton tried to exploit Assad’s diminished leverage. Between 1993 and 1996, Secretary of State Warren Christopher made almost thirty trips to Damascus, to broker a deal on the Golan Heights. I was on most of them. Several times, Christopher told the travelling press that he was close, very close. Clinton called on Assad in Damascus—the first Presidential visit since Nixon’s trip—in 1994. But a deal never jelled. In a last-ditch gamble before leaving office, Clinton met Assad again, in Geneva, in 2000. Assad spent much of the session lecturing the younger U.S. President about the history of Syria’s border with Israel and reiterating his demand for the return of the entire Golan Heights as a condition for peace.

An Arab envoy told the Times, ''He would rather die than not get full withdrawal. He hasn't changed his mind in thirty years, and he is not going to change his mind in a couple of hours in Geneva.'' Assad died just three months later. “He was a ruthless but brilliant man who had once wiped out a whole village as a lesson to his opponents,” Clinton wrote in “My Life.”