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.