advantage,” one former official said. “They didn’t have to do much to have a strategic effect.”

Richard Olson, who served as top envoy to Afghanistan and Pakistan under Obama, said other countries also engaged in hedging behavior as they scrambled to protect themselves from a possible breakdown.

“Everyone in the region has their links to the Taliban, so the U.S. needs to pursue a settlement that includes all of those players,” he said.

In August 2014, as the United States and its European allies imposed intensifying sanctions on Russia for its annexation of Crimea and support of separatists in eastern Ukraine, a small team of U.S. diplomats boarded a plane for Moscow.

With U.S.-Russia tensions skyrocketing, the diplomats had secured special White House permission to attend the first Moscow meeting of theRussian-initiated talks. Their instructions: Keep the gathering secret, and stay only as long as necessary.

Overseeing the discussion at the Foreign Ministry guesthouse, which also included Pakistan, India, China and Afghanistan, was Kabulov.

With his gruff humor, penchant for boozy meetings and ready catalogue of American stumbles overseas, U.S. diplomats saw Kabulov as the ultimate “Cold Warrior.”

The veteran diplomat had served at the Soviet Embassy in Kabul in the 1980s and 1990s and returned as Russia’s ambassador after the Taliban’s fall in 2001. He was one of a handful of outsiders to have met Mohammad Omar, the Taliban’s one-eyed leader, during a negotiation for a captured Russian aircrew in the 1990s.

Soviet troops near the city of Jalalabad in October 1986. (Viktor Habarov/PhotoXPress)

Johnny Walsh, a former State Department official focused on