“Just over there,” said the tall, dreary-looking man in the raincoat, gray hair topping his deep-set eyes and long face. He was standing just west of the Brandenburg Gate, beneath Berlin’s overcast sky, his finger pointing at something. “It was 1954,” he added, but that was all you could hear. Following in the Man’s wake was an amorphous mob that included a dozen photographers, American and German, snapping away on their $7,000 Canon 1D Xs. Others were Foreign Service Officers, or FSOs, divisible into three subspecies: the pony-tailed sci-fi nerds, who talked your ear off on the van ride from the airport; the slim-fit Thomas Pink metrosexuals, who scarcely looked at you while massaging their iPhones; and the liver-spotted lifers, who got their starts under Jimmy Carter and swore this would be their last posting. Also in tow were Diplomatic Security officers, their eyes hidden behind aviator shades as they muttered into miniaturized microphones, and their German counterparts, ripped dudes in pea-green vests with Polizei emblazoned across their backs.

Traveling press walks in the street! Herding us like cats was the State Department’s Ashley Yehl, a brown-haired Texan, 27 and already a veteran of VIP trips to 99 countries. Yehl was enjoining the American reporters from even thinking about walking on the cobblestones where the Man was leading the mob along a lordly half inch above the rest of us. Suddenly the Man—John Forbes Kerry, America’s 68th secretary of state—resumed his slow march across the Pariser Platz, and the mob slowly followed. Kerry was headed for the prime real estate just beside the gate that is home to the U.S. Embassy in Berlin.

Even amid the din, reporters understood Kerry’s reference to 1954. We called it the Bicycle Story. Kerry was 10 years old, the son of an American lawyer and FSO then serving as a legal advisor to the high commissioner of Germany. Clutching his diplomatic passport, the young Kerry, four-foot-11, mischievously pedaled through the Brandenburg Gate and a checkpoint, where he got an eyeful of how the other half lived in what was then, at the height of the Cold War, called East Berlin. “[I] noticed very quickly how dark and unpopulated and sort of unhappy people looked,” Kerry told the embassy staffers. After the wayward boy had apprised his father of his travels, the elder Kerry yelled his head off—“You could have been an international incident! I could have lost my job!”—grounded the kid and yanked his passport.

We had all heard the Bicycle Story multiple times by this point. The day before, at a news conference in London with British foreign secretary William Hague—at which the five-foot-10 and balding Hague, to reach height parity with the six-foot-four Kerry, had to stand on a concealed box—the secretary unspooled a different but similar yarn, this time about his having gotten lost, as a child, in the London Zoo. “I want to thank somebody for finding me,” he joked. The bonhomie continued when Kerry told Hague, “This day, I must say, was made much easier. It was impossible for me to get lost, Mr. Secretary. Thank you.”

These anecdotes were meant to be endearing: a conjuring of bygone childhood innocence amid the jangly nerves of the Cold War and a reminder to all listeners, in every venue, that Kerry was the first child of an FSO to lead the State Department. Surely it was proper for the new secretary to bring along three dozen policy aides and FSOs, a small battalion of photographers and the CBS News pool crew, plus the traveling press and all the DS agents and stern-faced Polizei in order that this august event, this perfectly poignant moment, should be recorded for posterity, no?

Except that the secretary had already performed this exercise the night before, when he had bolted from Berlin’s Hotel Adlon—where visitors pay $19,500 a night to stay in the Royal Suite (“host to political leaders and rock stars”)—and taken a handful of aides to do the same thing: walk to the Brandenburg Gate and wistfully recall the Bicycle Story. Kerry’s staff had even tweeted a photograph of it. So the presence the following morning of the mob was necessary solely to breathe oxygen into a pseudo-event, a photo op in which John Kerry, that act we in the press have known for years, feigned nostalgia.

It was a fitting prelude to the steeper plunge into unreality that awaited us. Germany was the second leg of our 11-day trek to 10 European and Middle Eastern countries, a grueling marathon that marked Kerry’s first overseas trip as America’s top diplomat. As a White House and State Department correspondent for Fox News, I had logged hundreds of thousands of miles on similar trips, accompanying presidents and vice presidents, secretaries of state and defense, over the preceding decade. But this time was different. Never before had the world seemed so in flux and the American economy so hobbled by self-inflicted wounds. This toxic cocktail of weakness at home and upheaval abroad—the Arab Spring, the Syrian civil war, Iran’s march toward nuclear weapons, the Israeli-Palestinian conflict, lawlessness in Afghanistan and Pakistan—would make anxiety and frustration our constant traveling companions. As John Kerry and I were to learn together, it’s just not a fun time to be secretary of state.

As chairman of the Senate Foreign Relations Committee the previous four years, Kerry had roamed the globe as an ex­officio envoy on behalf of President Obama. He met with implacable dictators, such as Bashar al-Assad of Syria, and prickly allies, such as Hamid Karzai of Afghanistan. The chairmanship capped Kerry’s nearly three decades in the Senate, which in turn followed his decorated service in Vietnam and celebrated conversion to leader of Vietnam Veterans Against the War. The Man, in short, knew his way around the world. Of the 40 leaders he met with on this trip—kings, presidents, prime ministers, foreign ministers—all but one he had met before. “I’ve known him for so long,” the U.S. ambassador in one of the European nations could be overheard telling a senior Kerry aide. “And I like him. He’s better at this”—meaning diplomacy—“than the president, in some ways.”

Kerry had maintained a constant presence in American political life. He introduced John Lennon to antiwar crowds, led the early congressional investigations into Iran-contra, spent decades as Massachusetts’s junior senator, laboring in the ever­expanding shadow of Ted Kennedy. But of all Kerry’s guises, the one most familiar to Americans in the 21st century is, let’s face it, that of loser—loser of the 2004 presidential election, the man who failed to oust George W. Bush from the White House, another in a long line of Democratic nominees painted, justly or unjustly, as soft, weak, indecisive: “I was for it before I was against it.” What few remember about 2004, however, is that if 60,000 Ohioans had gone the other way, President Kerry would have stretched out those long legs in the Oval Office.

As it happened, Kerry succeeded at State another well-known loser: Hillary Clinton, vanquished in the 2008 Democratic primaries by Barack Obama. Except no one sees Clinton that way. She left Foggy Bottom with record approval ratings, as well positioned today for the Democratic primaries of 2016 as she stood back in 2005, after Kerry’s defeat at the hands of Bush, for the 2008 contest. And while Clinton’s record as secretary is far from great—she logged the most miles and countries, yes, but no major peace accords or foreign-policy doctrines bear her name, and the threats posed by Iran, North Korea and Al­Qaeda’s evil stepchildren loom larger today than four years ago—her cautious, lawyerly demeanor, her focus on “safe” issues such as women’s empowerment and the veneration of the Washington intelligentsia make it common to hear the former first lady described as a “rock star” on the world stage: an exalted status that Kerry, whose rhetoric leans toward unlistenable, could never hope to match. “I have,” he quipped on his first day on the job, “big heels to fill.”

For Kerry’s aides, some imported from the Senate, others inherited from Clinton, the first order of business was to brand the new secretary’s interactions with overseas audiences. Clinton’s press wizard, the roguish Philippe Reines, had combined “town hall” and “interview” to dub Clinton’s road shows “townterviews,” a clumsy coinage that never stuck. At Base Camp, a hipster coffee bar in downtown Berlin where Kerry was to hold his first Q&A with young foreigners, a snazzy banner ginned up by embassy employees the day before our arrival signaled the path Kerry’s communications team had chosen. youth connect: berlin it read, with the Twitter logo and the inscriptions “#YouthConnect” and “#SecKerry.” The event was partially sponsored by Facebook. So that was the ticket: Sixty-nine-year-old John Kerry was to be repackaged as an avatar of the digital age.

FSOs had spent two days scouring Berlin for just the right venue. Told that the Youth Connect event seemed “Clintonesque,” an FSO confided, “I think that’s what they’re trying for.” Dotting the wall behind Kerry were electronic scoreboards, each blaring a one-word slogan such as Innovate or Botschaft (“message”), the lot of them linked by an ostentatious network of black cables that underscored the connectivity theme. The moderator was German TV personality Cherno Jobatey, a smiley-faced man with dark wavy hair, dark blazer, dark shirt, dark jeans and dark Chuck Taylors. Kerry, who has a gift for foreign languages—he demonstrated fluency in at least three on the trip—delighted the students with some German off the top. “Sehr gut, danke. Alles gut. Deine Schuhe sind fantastisch, ja?” (“Very good, thank you. All is good. Your shoes are fan­tastic, yes?”)

But it wasn’t long before Quintessential Kerry leaped to the fore. A pretty blonde student rose to ask about the emerging economies of Asia and Africa. Kerry’s response extended to almost 700 words, droning on for long and stifling minutes about the imbalance of agricultural regulations between East and West and the need for “the appropriate application of standards” to China’s health and environmental systems. The student was almost instantly lost and could soon be observed texting her friends. It brought back memories of the 2004 campaign, when TV reporters complained to Kerry’s press aides about his penchant for complex rhetorical constructions, his stately senatorial stacking of clause upon clause in great, wobbly towers of soaring Kennedyesque verbiage that became impossible to edit down and get on the six o’clock news. Kerry’s aides would shrug: “You’re preaching to the choir, dude.”

Now a Muslim woman, wearing the traditional cover and excited about her work with JUMA—a group for young followers of Islam who, as she put it, “stand up for righteousness, equality and tolerance”—wanted Kerry’s evaluation of religious tolerance in the United States. Kerry worked his way around to saying that Americans “live and breathe the idea of religious freedom and religious tolerance”—but not before tying himself into pretzels: “Because in America, we have total—occasionally, you have; I can’t tell you that a hundred percent—sometimes you have somebody who’s a little…not as tolerant as somebody else.”

To recover, the secretary figured he would acquaint these starry-eyed Berliners with the American legal tradition of respecting those forms of speech we find most obnoxious. He’d have been better advised to make merry again with host Jobatey, who mostly stood around looking befuddled and bored. “Some people have sometimes wondered about why our Supreme Court allows one group or another to march in a parade,” Kerry said, “even though it’s the most provocative thing in the world and they carry signs that are an insult to one group or another. And the reason is that that’s freedom—freedom of speech.”

Somewhere down in his soul, Kerry likely grasped that he had lost his audience, knew he was already closing in on 250 words in this answer and had failed to strike a chord, failed to #YouthConnect. The moment called for something dramatic, something the kids could relate to. Now Kerry thought he had it: “In America, you have a right to be stupid.” Nervous laughter ricocheted across the room. Immediately Kerry was off again, trying to explain what he’d meant, blathering something about how “you have a right to be disconnected to somebody else.” But the American reporters were all wincing.

#Yikes. From the whole two-hour event, “the right to be stupid” offered the only sound bite Reuters news agency fed to U.S. news markets across the Atlantic. It was not the kind of thing one expects to hear passing the lips of the U.S. secretary of state on foreign soil, let alone on his first overseas trip, and it definitely wasn’t Clintonesque.

For more than two years Syrian president Bashar al-Assad, a mass murderer like his father, had sought to quash a popular uprising against his tyrannical rule. The dictator had used virtually every military asset at his disposal: hundreds of thousands of soldiers, armored fighting vehicles, fighter jets, Scud missiles, heavy artillery. Many believed it was only a matter of time before Assad, increasingly desperate, unleashed the massive arsenal of biological and chemical weapons he was believed to possess. (Indeed, credible reports of chemical weapons use in Syria began to surface after our return to the U.S.) The United Nations estimated the conflict had already claimed 70,000 lives and sent more than 1 million Syrians fleeing to neighboring countries.

Yet Assad’s reduction of whole cities to rubble had only emboldened the Syrian rebels. That term, however—Syrian rebels—is a fiction, an umbrella term for a fractious coalition of fighters and civilians that hardly constitutes an organized opposition force, politically or militarily. At any given moment, the “rebels” will include democratic-minded revolutionaries Americans would approve of; ad hoc local brigades that scour abandoned armories for weapons and answer to no one; and hardened battle units such as the al-Nusra Front, probably the most effective fighting force currently confronting Assad’s troops. The only problem with al-Nusra is that it is openly allied with Al Qaeda. This has created a paradox: As Assad’s military position worsens, suffering high-level defections and surrendering control of provincial capitals and border regions, the situation grows more worrisome for the United States. As the U.S. ambassador to Syria, Robert Ford, testified before Congress, “The longer the conflict continues, the greater the influence of extremists on the ground.”

By the time Kerry was sworn in, the entire civilized world had condemned Assad’s butchery. Seated alongside Kerry in Riyadh, Saudi Arabia’s Prince Saud al-Faisal—the world’s longest-serving foreign minister, in his post since 1975—brandished for Assad words of contempt even the Israelis had never elicited. “I have never heard or seen in history,” the prince said, his speech slowed by advanced age and Parkinson’s disease, “that a regime would use a strategic missile toward his people. And [Assad] is killing innocent children, innocent women and old men. Nobody who has done that to his citizens can claim a right to lead a country.”

Worried about supplying weapons that would fall into the hands of al-Nusra fighters and eventually be turned against us—or against the Israelis—the Obama administration had long refused to help the rebels militarily (even though then Senator Kerry, in May of last year, had so urged). No such qualms have inhibited the Saudis, how­ever. Once Assad looked vulnerable, Riyadh swiftly assumed a lead role in arming and funding the Syrian opposition. In this the Saudis were joined by other oil-rich Sunni Arab nations in the Persian Gulf, most of which are eager to see the Shi’ite regime in Damascus collapse. The toppling of Assad would deal a huge strategic setback to Iran, the Shi’ite power whose regional bullying and pursuit of nuclear weapons have long posed a threat to the Sunni states.

Yet Iran was not the only authoritarian government propping up Assad. So was Russia. Despite having signed on to the Geneva Communiqué, a multilateral accord that calls for an orderly transition to a new and democratic Syria—i.e., one that does not include Assad—the Kremlin had steadfastly continued to back the regime throughout the crisis. Since the Soviet era, Kremlin warships have docked at a Russian naval base in the Syrian coastal city of Tartus, and military contracts between the two capitals are now estimated to be worth $4 billion. For these reasons, the Russians have consistently blocked meaningful action against Assad at the UN Security Council and kept up their deliveries of weapons to Assad’s forces. The Cold War is over, but Mother Russia remains strong, and President Vladimir Putin remains determined to check American power and influence wherever possible.

Accordingly, shaping up as one of the critical events on Kerry’s itinerary was his first sit-down as secretary with Russia’s notoriously acerbic foreign minister, Sergey Lavrov. Tall and bespectacled, an imposing figure with a deep voice and scowling mien, Lavrov has held his post for nearly a decade and has chewed up one secretary of state after another. At the Adlon in Berlin, a long table covered in white linen was set up in a conference room for the American and Russian sides, suitable for a major arms-control negotiation. Flanking Kerry, who was placed at the middle of the table, was State Department spokesperson Victoria Nuland; Phil Gordon, the assistant secretary for Europe and Eurasia, soon to move over to the National Security Council; Elizabeth Sherwood-Randall, a tall, blonde NSC officer, soon to receive a promotion to a more senior NSC post; Cynthia Doell, the official “note taker” for the American side; and U.S. Navy Vice Admiral Harry B. Harris Jr., a Tennessean with a chest full of medals and ribbons who was representing the Joint Chiefs of Staff. On Lavrov’s side, chairs were reserved for Alexander A. Tokovinin, director of the Russian foreign ministry’s Policy Planning Department; Evgeny S. Ivanov, Lavrov’s staff secretary; and note taker Oleg V. ­Pozdnyakov, among others. These officials are seldom glimpsed by the American press.

For an hour, Russian and American reporters rocked on their heels, waiting for the principals to appear and hungrily eyeing a platter of coffee and pastries that the Adlon’s German waitstaff had made clear was verboten. Then, suddenly, movement: Kerry and Lavrov shook hands and ambled over to a pair of microphones and flags set up in a corner so they could repeat the exercise for photographers. “We are happy to see each other,” Kerry said jovially. “We know each other and have had some good discussions.” Lavrov was in no mood for it, though, and swiftly administered poison gas to the merriment. He scowled at the reporters and said, in English, “If they get out, I will be able to get to my chair.”

With the reporters ushered out, sources said later, Kerry played possum while Lavrov harangued him with a long list of Kremlin grievances—not just on big topics such as Syria and Iran and Moscow’s recent decision to block Americans from adopting Russian children, but on small stuff, criminal cases unworthy of the occasion. Kerry, of course, has long experience with foreign leaders fond of lecturing Americans. There was good reason to believe the new secretary of state handled this moment with considerable deftness—or about as well as Sergey Lavrov can be handled—by structuring the nearly two-hour session in a way that maximized, at least in theory, the chances that Lavrov would honor his promises. When it was over, Kerry scooted off to more closed-door meetings. Lavrov, however, spoke to the news media—with his usual edge. “The discussion was, to my mind, constructive and in the spirit of partnership,” he said, “without, of course, ignoring the questions which are irritating these relations.”

What President Obama and Kerry wanted from the Russians, above all, was for President Putin to make a final break with Assad: to recognize that the dictator’s days were indeed numbered, as Obama had been saying since early 2012, and for Moscow to cease its supplies of arms and cash to the Syrian regime. The American message boiled down to this: If the Kremlin doesn’t wake up, it will soon find itself sharing with Washington the burden of dealing with a new Syrian government run by al-Nusra. Surely Russia’s billionaire oligarchs and the executives at Gazprom, the national gas behemoth, could be persuaded that the emergence of an Al Qaeda state in the heart of the Middle East would be bad for business.

The true measure of Kerry’s success in this opening duel with Lavrov would emerge a month later, on March 20, when Ambassador Ford told the House Foreign Affairs Committee,“We would like Russia, first of all, to stop delivering arms systems to the Syrian government. This is an ongoing conversation that we have with them.”

Kerry’s a toucher. The physical contact he initiated during our first 15 minutes on the plane together, as he strode the cabin and chatted with his new press corps, easily exceeded the sum total of my physical contact with cabinet officers in the previous 15 years. He would scrunch your shoulder while talking to someone else, like a kindly uncle. When he and a foreign counterpart shuffled offstage after a news conference, Kerry, invariably the taller man, would place his hand on his colleague’s back or shoulder, gently guiding his host out—in the host’s own foreign ministry. Near the end of the trip, when I arrived for our one-on-one interview, Kerry shook my hand, then drew me in for a bear hug, like a fraternity brother.

Far from displaying the cruelty some politicians are given to, Kerry is gentle in nature. He follows up jokes with “Only joking!” and strives to do all the right things. On a recent trip he traipsed down the aisle toting a birthday cake for Margaret Brennan of CBS News. On the last stop of our marathon, a refueling mission at the duty-free shoppers’ paradise of Shannon Airport in Ireland, Kerry returned to the cabin carrying shopping bags stuffed with tins of Irish toffee and chocolates, and tossed the sweets to us like Santa Claus. There were few people of consequence Kerry hadn’t met and about whom he couldn’t produce, on cue, a pleasing anecdote. Standing in the airplane aisle or seated over wine in a Middle Eastern hotel courtyard, Kerry might still be wearing the pin-striped pants from his suit or might have changed into jeans. He regularly wore a black alligator belt with a silver buckle; a button-down shirt open at the neck, sometimes denim with brown pearl buttons; and for warmth a salmon-colored Polo hoodie adorned with Native American stitching. Sometimes his history of knee troubles could be observed, but mostly Kerry still moved, at 69, with a kind of preppy athleticism. It gave you a sense of what he must have been like at St. Paul’s or Yale in the 1960s. I liked him.

But for someone with Kerry’s knowledge of the world and its leaders, his long experience in the fine art and crude realities of high-stakes international diplomacy, he made on this trip a surprising number of—there’s no other way to put it—rookie mistakes. The Americans as “stupid” business was only the beginning. At the Quai d’Orsay in Paris, where he fielded questions alongside French foreign minister Laurent Fabius, Kerry said, “Iran is a country with a government that was elected and that sits in the United Nations.” Again, the reporters cocked their heads. Was Kerry forgetting how the regime bloodied the streets of Tehran when the citizenry protested rigged elections in 2009?

Sometimes it was a matter of craft. Kerry routinely wound up talking longer than his hosts. His well-known weakness is wordiness: He is forever hoping people will “have the ability to be able to” do this or fretting something will “undermine our ability to be able to” do that. “The ability to be able to” was like a virus that followed us from country to country.

And in Ankara, appearing with Turkish foreign minister Ahmet Davutoglu, Kerry simply spaced out and forgot to wear his headphones while Davutoglu was speaking in Turkish. After realizing Kerry wasn’t listening to him, the foreign minister stopped and mused, “I think you start to understand Turkish.” Amid peals of laughter, Kerry hurriedly fumbled with the headphones. Davutoglu strained for something unifying (“We are speaking not from the tongue to the ear but from the mind to the mind”) and moved on.

Only once did Kerry get testy with a reporter. The undeserving victim was NBC State Department producer Catherine Chomiak. Chestnut-haired and slender, with impeccable manners and large eyes framed by exquisite features, Chomiak is the very picture of a stylish young professional. At the news conference in Riyadh she followed up a question about Iran with a routine query about what Kerry planned to discuss during his upcoming lunch with Palestinian president Mahmoud Abbas. “What do you think I might discuss with him?” Kerry snapped. A shudder rippled through the diplomatic corps; this was a guise we hadn’t seen. Kerry seemed to realize orneriness had gotten the better of him. The moment called for him to snap out of his funk and give Chomiak a substantive preview of the Abbas luncheon—something long enough, in any case, to dim the memory of his rudeness. But Kerry, perhaps fatigued in this, our seventh country in eight days, couldn’t be bothered. He mumbled perfunctorily about looking forward to the meeting and volunteered only that he and Abbas would discuss “all the obvious issues.”

Kerry’s frustration could perhaps be forgiven. At his Senate confirmation hearing on January 24 he had conveyed his belief that things were changing rapidly and profoundly and in such unpredictable ways, to the point that he seemed to be hinting at the unspeakable, namely that the challenges confronting American diplomats might be insurmountable. “Today’s world is more complicated than anything we have experienced,” Kerry told his old colleagues on the Foreign Relations Committee. He quoted his old nemesis from the Vietnam era, Henry Kissinger: “None of the most important countries which must build a new world order have had any experience with the multistate system that is emerging. Never before has a new world order had to be assembled from so many different perceptions or on so global a scale. Nor has any previous order had to combine the attributes of the historic balance-of-power system with global democratic opinion and the exploding technology of the contemporary period.”

In lay terms, this means the old framework that has effectively governed international relations since World War II is coming apart. Leading nations, no less than internet giants, terrorist groups and criminal syndicates, blithely brush aside UN Security Council resolutions and other unenforceable constructs of international law. There’s no unwritten pecking order of states anymore, no impenetrable nuclear club. The old order installed by FDR, Stalin, Churchill and de Gaulle in 1945 is being replaced by—who the hell knows? The post-9/11 era is proving to be just shy of anarchic. At the hearing, Kerry, in his usual style, reeled off 10 modern developments that herald this death of the old order: “the emergence of China; the Arab Awakening; inextricably linked economic, health, environmental and demographic issues; [WMD] proliferation; poverty; pandemic disease; refugees; conflict ongoing in Afghanistan; entire populations and faiths struggling with the demands of modernity; and the accelerating pace of technological innovation invading all of that, shifting power from nation-states to individuals.”

All this, in short, is why no American secretary of state, upon assuming office, really expects to succeed anymore, to forge demonstrable progress on the major problems, or “challenges,” of our time, the way secretaries of state from both parties once appeared able to do. Moreover, Kerry’s ascent to the pinnacle of American diplomacy comes in the #epicfail era, an epoch of suffocating U.S. debt, an almost comically dysfunctional slog through slowdowns and sequesters, fiscal cliffs and ratings downgrades, perpetually uneven job creation and quarterly growth. Secretary Clinton had warned about the constricting effect our nation’s dismal finances, including the large share of our debt owned by China, can have on America’s ability to influence people and events overseas: the very mission of the State Department. In such a time, American swagger abroad ain’t what it used to be.

Secretary Kerry found this out the hard way. From London he’d been forced to plead, in a desperate telephone call, for Sheikh Moaz al-Khatib, the civilian leader of the “Syrian rebels,” to show up at a major conference in Rome—the centerpiece of Kerry’s trip—at which the U.S. was to announce a fresh pledge of $60 million in nonlethal aid to the opposition. To recap: At a time when Washington lawmakers were debating which vital domestic spending programs to cut, the U.S. wanted to give the Syrian rebels $60 million worth of stuff—and the secretary of state practically had to beg their leader to show up. And when the wiry al-Khatib arrived at Villa Madama, the bucolic Italian foreign ministry, he scarcely grunted out a thank-you to Kerry or to the Italian foreign minister, Giulio Terzi, before launching into an Arabic rant that rebuked the allies for their preoccupation with al-Nusra. “I am tired of [this],” al-Khatib said, close to shouting, through his translator. “The mass media pay more attention to the length of the beard of a fighter than to the [government’s] massacres. No terrorists in the world have such a savage nature as that of the Syrian regime.” Kerry could only stand there, occasionally stiffening his spine and blinking with annoyance. Three weeks later al-Khatib announced his resignation.

In Cairo, Kerry’s feckless interlocutor was the Muslim Brotherhood government led by Egyptian president Mohamed Morsi, whose poor economic stewardship and ham-fisted power grabs had given rise to bloody unrest in major cities. A few months earlier a videotape from 2010 had surfaced in which Morsi, a bearded man with thick eyeglasses and a deceptively benign visage, declared Jews “the descendants of apes and pigs” and urged Egyptians to “nurse our children and grandchildren on hatred” for them. The leaders of the major civil-society opposition groups in Egypt—the individuals who represented Washington’s best hopes for displacing Morsi and the Brotherhood and restoring to power a more reliable ally in the world’s most populous Arab nation—refused to be seen with Kerry. One opposition figure skulked into a private session with the secretary of state; the other spoke with him by phone. The interior minister refused to provide Kerry’s motorcade with an escort from the airport to the Cairo Sheraton. And neither Morsi nor his foreign minister held a news conference with Kerry.

The secretary’s mission in Cairo was to prod major interest groups there to take shared risks to stop Egypt’s downward spiral since the heady days of Tahrir Square. “It is paramount, essential, urgent that the Egyptian economy get stronger,” Kerry told the business leaders. “You have to get people back to work, and the energy of this country needs to hopefully be able to move from the streets to enterprise.” He urged the opposition not to boycott parliamentary elections set for April. He implored the financial community to invest more in women and education. Most important, he leaned on Morsi to press forward with some unpopular economic measures—raising taxes, eliminating sacred-cow subsidies—so Egypt could qualify for a $4.8 billion International Monetary Fund loan, a deal the Obama administration was eager to advance. Until now, though, Morsi’s true intentions—toward the IMF, America, Israel, Jews, democracy, you name it—remained difficult for Kerry and his aides to discern.

State Department officials later said the principals’ session lasted two and a half hours, including an hour of one-on-one time. Kerry emerged from it so persuaded of Morsi’s sincerity in pledging to administer the IMF reforms and extend an olive branch to his political opponents that Kerry decided on the spot to unlock $250 million in frozen U.S. aid. Within 72 hours the same aides stood in the same airplane cabin and informed us that the Egyptian Supreme Court had just canceled the parliamentary elections set for April and that the intentions of Morsi and the Brotherhood were again proving difficult to discern.

The final leg, a tour of Persian Gulf nations, proved anticlimactic. Nothing in Saudi Arabia, the United Arab Emirates or Qatar matched the architecture: sprawling hotel complexes with hundred-foot ceilings, turrets and arches, brand-new Disneyesque castles with Bellagio-style fountains and hypnotic Arabic design swirls. On our return, little from the trip seemed to have exerted a lasting impact on world affairs. In April a 25-year-old FSO from the Chicago area named Anne Smedinghoff was killed during a suicide-bomb attack in Afghanistan just days after she had served as support staff for a Kerry visit there. For many the episode, which moved Kerry deeply, conjured the killings at Benghazi on September 11, 2012, the last time U.S. diplomatic personnel had been lost to violence. I recalled my conversation with two FSOs in a Middle Eastern country during the trip. A young woman, probably Smedinghoff’s age, was lamenting how little attention Americans pay to the work of their diplomats. “How do we change that?” she asked. “Easy,” said her colleague, a sci-fi nerd. “Get killed in the line of duty.” Leading these dazed shock troops in the titanic struggle of ideologies—what Kerry likes to call “the clash of modernity”—is a secretary of state who, regardless of how you feel about his politics, was born for the job, has all the experience and tools, knows the geography and players, sailed through his Senate confirmation 94–3 and who, despite all that, represents a dysfunctional government and encounters a world whose hostility seems only to grow.

Every sign of progress in establishing a new order that Kerry might have “the ability to be able to” observe yields, sooner or later, to encroaching anarchy. America still has some money to give away, but as Kerry wanders the boneyard of ideas between engagement and isolation, brandishing his carrots and sticks and making his 10-point arguments for why the developing world should embrace liberal democracy over authoritarianism and radical Islam, the response is too often rooted in sheer perversity, a Bizarro World inversion of, or just plain disregard for, everything the West considers the inherited wisdom of the ages. Up is down! maintain the Russians and the Chinese, the mullahs in Iran, Assad, al-Nusra, Morsi, Karzai. Black is white! God is on our side! The old order is dead!

The diplomat who understands this best is Prince Saud al-Faisal, the dean of foreign ministers. On Hillary Clinton’s last visit to Riyadh, a year before Kerry arrived there, the prince told her, “We are living in a world where truth and falsehood have become mixed.”