Find­ing lessons fol­low­ing dis­as­ter

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Jake Sul­li­van, who was the se­nior pol­icy ad­viser to Hil­lary Clin­ton dur­ing her 2016 run for president, is search­ing for mean­ing fol­low­ing a shock­ing loss.

If all had gone as planned, and as most in Washington had ex­pected, Jake Sul­li­van would be hard at work just steps from the Oval Of­fice. He was the elite of the Washington elite: Rhodes scholar, Yale Law School grad­u­ate, clerk to a Supreme Court jus­tice, the per­son at Hil­lary Clin­ton’s side when she cir­cled the world as sec­re­tary of state, a steady voice in the Sit­u­a­tion Room for President Barack Obama.

The con­ven­tional wis­dom held that Sul­li­van was a lock to be the na­tional se­cu­rity ad­viser in a Clin­ton ad­min­is­tra­tion. At 40, he would have been the youngest to hold that po­si­tion in U.S. his­tory.

In­stead, Don­ald Trump won the pres­i­dency, and Sul­li­van says he some­times feels like a “ghoul­ish re­minder” to friends of an elec­tion that shook the Washington es­tab­lish­ment like no other in decades.

On a re­cent even­ing, he was push­ing open a bat­tered or­ange door, climb­ing stairs covered with fray­ing car­pet and strid­ing into a dimly lit apart­ment where two dozen Yale Law School stu­dents were wait­ing to hear from him. Most of them were des­per­ate for some ver­sion of the life he had led in Washington.

Sul­li­van, though, has never felt less cer­tain about where both he and his coun­try are headed. He di­vides his time be­tween an empty think tank of­fice in Washington and Yale, where he lec­tures one day a week on law and for­eign pol­icy. Al­most every­thing about his pro­fes­sional life is tran­si­tory, un­cer­tain, un­set­tled.

“I feel a keen sense of re­spon­si­bil­ity for the out­come,” he told friends in the im­me­di­ate af­ter­math of Clin­ton’s de­feat. Months later, the feel­ing had not faded.

Clin­ton and oth­ers in her in­ner­most cir­cle of ad­vis­ers of­ten speak of the elec­tion as if it had been stolen from them. They rage against Rus­sian in­ter­fer­ence, com­plain about the last-minute dis­clo­sures by for­mer FBI di­rec­tor James B. Comey, and crit­i­cize Obama’s un­will­ing­ness to take a more

With ‘the hu­mil­ity of the de­feated,’ top Clin­ton ad­viser Jake Sul­li­van searches for mean­ing in a shock­ing loss BY GREG JAFFE IN NEW HAVEN, CONN. “I am still los­ing sleep. I’m still think­ing about what I could have done dif­fer­ently.” Jake Sul­li­van, Hil­lary Clin­ton’s se­nior pol­icy ad­viser, shown be­low sit­ting for a por­trait at the Carnegie En­dow­ment for In­ter­na­tional Peace

force­ful line with Rus­sian President Vladimir Putin.

“Re­mem­ber, I did win more than 3 mil­lion votes [more] than my op­po­nent,” Clin­ton said in a re­cent in­ter­view.

Sul­li­van, more than most in the Clin­ton or­bit, has be­gun to shoul­der blame for the loss and his role in it. He wants to un­der­stand his mis­takes and fig­ure out how to fix them.

“I have the hu­mil­ity of the de­feated,” he says as if it were a mantra.

On this night, Sul­li­van set­tled into a ragged, hand-me-down chair at the front of the Yale stu­dent apart­ment and looked around at the room full of smart, am­bi­tious young peo­ple. He bal­anced a plate of greasy pizza on his lap. Some­one handed him a beer.

“You all know Jake Sul­li­van,” a sec­ond-year law stu­dent said by way of in­tro­duc­tion.

‘Have you bounced back?’

Ev­ery­one in­volved in Washington pol­icy knew Jake Sul­li­van, or at least they knew of him.

For years he had been dis­cussed as the next in a long line of gray-suited Washington wise men dat­ing back to the end of World War II. The late diplo­mat Richard Hol­brooke in­sisted that he had all the mak­ings of a fu­ture sec­re­tary of state. Clin­ton con­fided to friends that she thought he could be president.

Sul­li­van gazed out the win­dow down Hill­house Av­enue, a stretch of road that Mark Twain had called “the most beau­ti­ful street in Amer­ica,” and in the di­rec­tion of the apart­ment — three blocks away — where he had lived as a law stu­dent in the early 2000s. The stu­dents were clad mostly in jeans and sweat­shirts. Sul­li­van wore the uni­form he fa­vors when out­side of Washington — suit pants, a solid but­ton-down dress shirt and no tie. His hair was combed in a ruler-straight part.

He ran through a list of his early men­tors who had helped him find pur­chase in Washington: There was Les­lie H. Gelb, the for­mer president of the Coun­cil on For­eign Re­la­tions, where Sul­li­van had spent time as a sum­mer in­tern, as­signed by hap­pen­stance to Gelb’s of­fice.

There was Strobe Tal­bott, who runs the Brook­ings In­sti­tu­tion. In 2000, when Sul­li­van was start­ing law school, Tal­bott had just been cho­sen to lead the newly formed Yale Cen­ter for the Study of Glob­al­iza­tion. “Those were the heady days when the main­stream for­eign pol­icy con­sen­sus was that glob­al­iza­tion was a force for good,” Sul­li­van re­called. He had sought out Tal­bott af­ter learn­ing that they had both been Rhodes schol­ars and edited the Yale Daily News.

There was Hol­brooke, who on Gelb’s rec­om­men­da­tion had sug­gested Sul­li­van to Clin­ton when she was run­ning for president the first time. And fi­nally, there was Clin­ton her­self, who adored and trusted Sul­li­van and had made him part of her in­ner­most cir­cle of ad­vis­ers.

“It’s about seiz­ing op­por­tu­ni­ties and say­ing ‘yes,’ ” Sul­li­van said of his ca­reer and two un­suc­cess­ful Clin­ton pres­i­den­tial runs. He paused and added wryly: “If you do that, you can take part in not one but two elec­tion catas­tro­phes.”

Clin­ton tapped him in 2012 to help start se­cret talks with Iran over its nu­clear pro­gram, and when she left gov­ern­ment, Obama brought him to the White House, where Sul­li­van was part of the small group in the Oval Of­fice each morn­ing for the president’s daily in­tel­li­gence brief­ing.

The stu­dents pep­pered Sul­li­van with ques­tions about the Iran ne­go­ti­a­tions. Those ques­tions, though, were largely a pre­lude to the sub­ject that was re­ally on their minds: the elec­tion, its af­ter­math and the longterm prospects for peo­ple like them in Washington.

“We were all dev­as­tated by the elec­tion,” a third-year law stu­dent said. “Have you bounced back?”

“If fill-in-the-blank Repub­li­can had won, I would feel like things were pretty good for me,” Sul­li­van replied.

For the first time in a decade, he had week­ends off. He loved teach­ing. He was newly mar­ried. “But, the Trump fac­tor makes it hard,” he said. “I am still los­ing sleep. I’m still think­ing about what I could have done dif­fer­ently.”

An­other law stu­dent pressed harder on the wound. “Do you have a the­ory about what hap­pened?”

“I don’t know,” Sul­li­van said. He paused and stared at the ceil­ing.

“You don’t have to . . .” the stu­dent added, fear­ful that he had pushed too far. Sul­li­van con­sid­ered his an­swer for a few more awk­ward sec­onds.

“It’s a con­ver­sa­tion for bet­ter pizza,” he replied.

In other fo­rums and at other din­ners Sul­li­van was some­times will­ing to wres­tle with a ver­sion of the stu­dent’s ques­tion. At the Har­vard Fac­ulty Club a few weeks ear­lier, a for­mer Bri­tish par­lia­men­tar­ian, who in 2015 had lost his seat to a 20-year-old Scot­tish Na­tion­al­ist, de­scribed the prob­lem as he saw it.

“It’s a fight be­tween politi­cians with an­swers and politi­cians with anger,” he had said.

“I get PTSD just hear­ing that,” Sul­li­van had replied.

Sul­li­van’s post-trau­matic stress dis­or­der that night led him to flash back to an ar­gu­ment with Clin­ton on her cam­paign plane. He was her se­nior pol­icy ad­viser but was wor­ried that her pre­scrip­tion-heavy speeches were miss­ing the point of the elec­tion.

“Maybe we should just fo­cus on di­ag­nos­ing the prob­lem and re­lat­ing to peo­ple’s pain?” he re­called sug­gest­ing to her dur­ing her pri­mary bat­tle with Sen. Bernie San­ders of Ver­mont.

“No,” Clin­ton had replied. “This is a job in­ter­view. Peo­ple want to know how I am go­ing to fix it.”

Sul­li­van said he re­grets not push­ing the is­sue, even as it be­came more and more ev­i­dent that the gen­eral elec­tion wasn’t go­ing to be de­cided on pol­icy.

In the cam­paign’s fi­nal days, Sul­li­van was more ner­vous than most on the Clin­ton team that the elec­tion was slip­ping away. His col­leagues chalked it up to his fret­ful and fre­quently self­crit­i­cal na­ture. “He has a ten­dency to wear the hair shirt,” one for­mer col­league said.

Now Sul­li­van won­ders whether he should have pressed Clin­ton harder to dial back the pol­icy pre­scrip­tions in fa­vor of em­pa­thy or pos­si­bly even a lit­tle out­rage. “I mean, ‘ Build the wall’ is not re­ally a pol­icy so­lu­tion,” he said. “It’s a state­ment that gets to the heart of peo­ple’s con­cerns about im­mi­gra­tion and . . . iden­tity.”

But, be­fore he goes too far, a de­fen­sive­ness of Clin­ton and his role in the cam­paign takes hold. “It’s all about telling peo­ple that you get what they are go­ing through and Hil­lary was cer­tainly ca­pa­ble of that and had some in­cred­i­ble mo­ments and dis­plays of that,” Sul­li­van con­tin­ued. He played down the sig­nif­i­cance of his ex­change with Clin­ton on the plane.

“That’s more of cam­paign tac­tics is­sue,” he said.

Some­thing au­da­cious

Some­times when he’s search­ing for an­swers, Sul­li­van thinks back to the fourth night of the Demo­cratic Na­tional Con­ven­tion, when Khizr Khan, whose son was killed in Iraq, pulled a pocket-size Con­sti­tu­tion from his suit jacket and scolded Trump for tram­pling Amer­ica’s high­est ideals.

“We had our an­swer,” Sul­li­van told the Yale stu­dents. “The flag sig­ni­fied a great coun­try, an in­clu­sive coun­try, a gen­er­ous coun­try.”

But the cam­paign never suc­ceeded in turn­ing that mo­ment into a uni­fy­ing mes­sage, and the pres­i­den­tial de­bate soon re­turned to di­vi­sive is­sues of race, im­mi­gra­tion, in­equal­ity, abor­tion and trans­gen­der bath­rooms, he said.

“I used to be­lieve we just needed to take that night and stretch it over the span of the cam­paign,” Sul­li­van said. “But that’s not a so­lu­tion, be­cause you still have to deal with real is­sues. Our agenda in­volves a lot of ideas that are still con­tro­ver­sial.”

Sul­li­van was go­ing on about the “grow­ing” and “scary” di­vide in the coun­try when a law stu­dent from a ru­ral town in Ken­tucky in­ter­rupted his mono­logue: “Com­ing from a fly­over state, it is dif­fi­cult for me to even be on the same wave­length as the peo­ple I grew up with.”

The stu­dent’s con­fes­sion brought Sul­li­van back to his own up­bring­ing in Min­nesota. He was 13 when the Ber­lin Wall fell in 1989. A few months later, Soviet leader Mikhail Gor­bachev, ea­ger to meet with some av­er­age Amer­i­cans, vis­ited a home in Sul­li­van’s Minneapolis neigh­bor­hood. Sul­li­van re­mem­bered Lat­vian and Es­to­nian Amer­i­cans protest­ing for Baltic in­de­pen­dence along the Soviet pre­mier’s mo­tor­cade route. He felt a sense of what Amer­ica could mean to the world.

As a can­di­date, Trump had re­jected the very idea of American ex­cep­tion­al­ism as an un­nec­es­sary bur­den. “I don’t think it’s a very nice term. We’re ex­cep­tional. You’re not,” Trump had said at a tea party rally in Texas. “I want to take every­thing back from the world that we’ve given them. We’ve given them so much, "Sul­li­van in­creas­ingly thought that the an­ti­dote to Trump­ism was a full-on em­brace of American ex­cep­tion­al­ism of the sort he had felt in Min­nesota. “We need some­thing au­da­cious that’s rooted in our na­tional DNA; who we are as a peo­ple,” he said. “There needs to be a call to arms that can mo­ti­vate peo­ple.”

But he strug­gled to de­scribe his idea in de­tail. To spur his think­ing, he read a dense 1890 es­say by mil­i­tary strate­gist Al­fred Thayer Ma­han, mak­ing the case for Amer­ica as a global naval power. He stud­ied his­to­rian Stephen Kinzer’s book, “The True Flag,” on Theodore Roo­sevelt, Mark Twain and the birth of the American em­pire.

He played with ideas that he hoped might res­onate in Min­nesota or Ken­tucky. “Our ex­cep­tion­al­ism is rooted in the idea that we have the abil­ity to in­no­vate and solve hard prob­lems — cli­mate change, pan­demics, nu­clear pro­lif­er­a­tion,” he posited at one point. Maybe Amer­ica’s ex­cep­tional mis­sion was rooted in an un­shak­able com­mit­ment to a strong and grow­ing mid­dle class, he sug­gested a few weeks later.

But none of these for­mu­la­tions seemed big, au­da­cious or in­spir­ing enough.

Sul­li­van of­ten in­sisted that he had de­vel­oped his views about the world at “a public high school in Minneapolis.” But he is also un­ques­tion­ably a prod­uct of Washington’s in­su­lar for­eign pol­icy elite.

Even as par­ti­san ran­cor took hold in the coun­try, these Repub­li­can and Demo­cratic in­ter­na­tion­al­ists had long in­sisted that they were dif­fer­ent. They agreed on the big­gest is­sues: The United States had a unique moral au­thor­ity in the world and bore a spe­cial lead­er­ship bur­den. Al­most the en­tirety of the Repub­li­can for­eign pol­icy es­tab­lish­ment had signed let­ters op­pos­ing Trump’s can­di­dacy.

Sul­li­van em­bod­ies many of these elites’ courtli­est qual­i­ties. He does not shout down oppo- nents or even tweet. Many Repub­li­cans have kind words for him. “He has a huge amount of in­tegrity,” said Mark Dubowitz, an out­spo­ken critic of the Iran nu­clear pact. “You don’t get talk­ing points and an un­will­ing­ness to ac­knowl­edge prob­lems from him.”

As a can­di­date and even in of­fice, Trump chal­lenged just about ev­ery for­eign-pol­icy piety. He trash-talked Amer­ica’s al­liances, ques­tioned the wis­dom of nu­clear non­pro­lif­er­a­tion ef­forts and re­jected the ideal of a U.S. for­eign pol­icy built around demo­cratic val­ues, hu­man rights and en­light­ened self-in­ter­est.

The re­sponse from Washington barely res­onated out­side of the Belt­way. “We be­lieve that aban­don­ing tra­di­tional U.S. sup­port for the in­ter­na­tional or­der would be a se­ri­ous strate­gic er­ror that would leave the United States weaker and poorer, and the world more dan­ger­ous,” read a re­cent Brook­ings report put to­gether by a team of Washington lu­mi­nar­ies that in­cluded Sul­li­van.

Lately, he had be­gun to ques­tion the worth and wis­dom of these ef­forts. For years, the for­eign pol­icy es­tab­lish­ment has preached the im­por­tance of sus­tain­ing the U.S.-led, rules-based in­ter­na­tional or­der — an ex­hor­ta­tion that, at best, was mean­ing­less to most Amer­i­cans. At worst, it smacked of soul­less glob­al­ism.

To Sul­li­van, the most strik­ing ex­am­ple of the es­tab­lish­ment’s in­tel­lec­tual ex­haus­tion was the mam­moth 12-na­tion Tran­sPart­ner­ship trade deal that Trump of­fi­cially aban­doned ear­lier this year. Repub­li­can and Demo­cratic na­tional se­cu­rity an­a­lysts for years had touted the pact as es­sen­tial to U.S. na­tional se­cu­rity and con­tain­ing China. Sul­li­van had sup­ported it, too.

But few of those ex­perts, he said, paid any at­ten­tion to the de­tails of the pact and its po­ten­tially neg­a­tive ef­fects on American work­ers. In­stead, they as­sumed that free trade was a net pos­i­tive and fo­cused on other is­sues, such as mar­itime dis­putes over is­land chains in the South China Sea, Sul­li­van said. In the process, the elite lost touch with the con­cerns of the very peo­ple it was sup­posed to serve and de­fend.

The gulf, Sul­li­van in­sisted, was symp­to­matic of a much larger prob­lem.

“How do we solve for this ba­sic and grow­ing divi­sion in our so­ci­ety that gets to is­sues like dig­nity and alien­ation and iden­tity?” Sul­li­van asked. He caught the eye of the young law stu­dent from Ken­tucky, sit­ting just a few feet away from him. “How do we even ask the ques­tion with­out becoming the dis­con­nected, con­de­scend­ing elite that we are talk­ing about?” Sul­li­van asked.

The ques­tion hung in the air.

Home away from Washington

Sul­li­van be­gan to think re­cent- ly that he could more eas­ily an­swer these ques­tions if he moved away from places such as Washington, Har­vard or Yale.

“That’s not a value state­ment about who con­sti­tutes the good peo­ple of the land,” he said in an in­ter­view. “I don’t think that by go­ing to live in Min­nesota or New Hamp­shire or Tulsa, all of a sud­den you’re gain­ing wis­dom you can’t gain else­where. But you do gain a per­spec­tive. You’ll see things from a dif­fer­ent van­tage point, and that mat­ters.”

Sul­li­van’s first move when he fin­ished his Supreme Court clerk­ship in 2005 was to re­turn home. He had turned down a $250,000 sign­ing bonus from a big firm in Washington to ac­cept a po­si­tion with a smaller law prac­tice in Minneapolis that fo­cused on the agri­cul­ture and food in­dus­tries.

Back then, he imag­ined a life split be­tween gov­ern­ment ser­vice in Washington and a more nor­mal ex­is­tence in Min­nesota. “In Washington every­thing is built around the job be­cause the jobs are all-con­sum­ing,” he said. “In Min­nesota the job is one as­pect of your life.”

Sul­li­van had planned to move back to Min­nesota in 2013 when Clin­ton left the State Depart­ment. He was think­ing about run­ning for Congress or becoming a U.S. at­tor­ney, but Obama per­suaded him to come to the White House. “Obama’s pitch was that you can al­ways go home,” said Ben Rhodes, a top for­eign pol­icy ad­viser to the president at the time. “That’s never go­ing away, but here’s an op­por­tu­nity to work at the high­est lev­els of the White House and you never know when that’s go­ing to come around again.”

Even af­ter he fin­ished his White House job, Sul­li­van re­mained tied to Washington through the Clin­ton cam­paign and through his wife, who is sched­uled to be­gin a clerk­ship with Supreme Court Jus­tice Stephen G. Breyer that will keep them in the na­tion’s cap­i­tal for at least an­other year.

Then the plan is to leave Washington next year and set­tle some­place where he can put down roots. He imag­ines becoming in­volved in com­mu­nity projects where the re­sults will be more real, im­me­di­ate and tan­gi­ble. Min­nesota is one op­tion. New Hamp­shire, where his wife grew up, is an­other.

The other pos­si­bil­ity is that he stays. “I have given up hope of look­ing peo­ple in the eye and telling them we are mov­ing any­where, based on the last decade,” Sul­li­van said.

It’s rare for any­one at Sul­li­van’s level in the for­eign pol­icy world to leave Washington or re­turn home. The is­sues have be­come too com­pli­cated. The money is too good. One Asian coun­try re­cently of­fered Sul­li­van $25,000 for a two-day visit.

“What’s that all about?” he re­called think­ing be­fore turn­ing it down.

The Yale stu­dents’ wor­ries, mean­while, ran in the opposite di­rec­tion. They fret­ted about the op­por­tu­ni­ties still avail­able to peo­ple like them in Trump’s Washington.

“Is this the death knell of the tech­noc­racy and the elite?” one stu­dent asked, sum­ma­riz­ing the the­sis of a re­cent widely read ar­ti­cle in For­eign Af­fairs mag­a­zine.

Be­fore Sul­li­van could an­swer, an­other stu­dent clar­i­fied: “Is there a coastal elite 2.0, or are we all fin­ished?”

Sul­li­van wasn’t the sort to suc­cumb to the prophe­cies of doom that had taken hold in some sec­tors of Washington and academia. Even Trump still de­pended on his own ver­sion of the Washington elite, Sul­li­van told the Yale stu­dents. The president leaned heav­ily on gen­er­als to ex­e­cute his for­eign pol­icy; his Cab­i­net was stacked with bil­lion­aires. “Gold­man Sachs is run­ning our eco­nomic pol­icy,” Sul­li­van said. “So there will al­ways be a de­mand for ex­per­tise.”

Sul­li­van’s even­ing with the Yale stu­dents was near­ing its end. The sky out­side had grown dark. His slice of pizza was cold on his plate.

“I still be­lieve pas­sion­ately in find­ing a home out­side of D.C.,” he said.

“Vir­ginia or Mary­land?” one of the Yale stu­dents joked.

“Maybe,” he con­tin­ued, “the best ser­vice I can ren­der right now is out­side of Washington.”

Sul­li­van edged to­ward the door. The next day he planned to meet with Clin­ton in New York to re­view her mem­oir, and maybe, if they fin­ished in time and he wasn’t too tired, at­tend a din­ner with the French am­bas­sador. Back in Washington.

“How do we solve for this ba­sic and grow­ing divi­sion in our so­ci­ety? . . . How do we even ask the ques­tion with­out becoming the dis­con­nected, con­de­scend­ing elite?” Jake Sul­li­van




TOP: Jake Sul­li­van, an ad­viser to Hil­lary Clin­ton when she was sec­re­tary of state, talks to her dur­ing a pause in tes­ti­mony be­fore the House Se­lect Com­mit­tee on Beng­hazi in Oc­to­ber 2015. Sul­li­van, re­garded as a pos­si­ble na­tional se­cu­rity ad­viser in a Clin­ton White House, di­vides his time be­tween a Washington think tank and Yale.

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