Jim Webb’s Populist Zeal

Can Jim Webb spark an anti-Hillary uprising?

Sen. Jim Webb at his Arlington, Va. office on Feb. 5, 2015.
National Journal
Bob Moser
Feb. 13, 2015, midnight

Could that be Jim Webb? Across the park­ing lot of the Eden Cen­ter, a Vi­et­namese-Amer­ic­an strip mall in the Wash­ing­ton sub­urb of Falls Church, I’ve spot­ted a smallish fig­ure in a tan ball cap, jeans, and boots, huddled against the bit­ter cold of an early Feb­ru­ary af­ter­noon and peer­ing around. Webb’s com­mu­nic­a­tions dir­ect­or, Craig Craw­ford, had told me to meet the one-term Vir­gin­ia sen­at­or un­der the Vi­et­namese flag—the old South Vi­et­namese flag, ac­tu­ally, the bright yel­low one with the red stripes. That’s where this fel­low is stand­ing. Even as I draw closer, and he waves tent­at­ively, he looks less like a man who might be run­ning for pres­id­ent than an early re­tir­ee run­ning er­rands. But it’s Jim Webb, all right. If there were any doubt, it’s gone once he gets on the phone with Craw­ford, who has got­ten lost on the spidery high­ways of North­ern Vir­gin­ia. “Where are you?” Webb barks in­to his phone. “Do you see the Vi­et­namese flag? What? What are we do­ing? We’re out here freez­ing our asses off!”

He shoots me a con­spir­at­ori­al grin, as if to re­as­sure me that he’s only mock-angry—not flash­ing the tem­per that folks in Wash­ing­ton are forever tut-tut­ting about—then says, “Come on.” He leads the way to­ward his fa­vor­ite “hole-in-the-wall” res­taur­ant, the Banh Cuon Sai­gon. There’s a limp in his gait; he had ma­jor knee sur­gery in early Janu­ary—a res­ult of linger­ing wounds from com­bat in Vi­et­nam, where he served with a Mar­ine pla­toon nick­named the “Dy­ing Delta” and earned the Navy Cross, two Purple Hearts, and shrapnel in his skull, kid­ney, and knee. The red in his hair, which al­ways seemed to ac­cord so well with his im­pol­it­ic brand of polit­ics, has been los­ing the battle to gray. But when he doffs his cap upon en­ter­ing the café—a good South­ern boy wouldn’t dare wear a hat in­side—Webb looks young for a soon-to-be-69-year-old, sharp-eyed, in fight­ing trim.

The nor­mally ta­cit­urn Webb is in an ex­pans­ive (for him) mood, though he’s not go­ing to talk about Hil­lary Clin­ton; he’s keep­ing his powder dry, it seems, in case he de­cides to de­ploy it. He comes to the Eden Cen­ter a lot, he says. It’s close to his house, and the mingled smells from the fish and meat shops and res­taur­ants take him back to Vi­et­nam, where his post­war memor­ies, at least, are fond ones: Webb spent part of the 1990s help­ing to open up trade with Vi­et­nam, and his third and cur­rent wife, Wash­ing­ton law­yer Hong Le Webb, was raised by a fam­ily who es­caped Sai­gon the day be­fore it fell. After or­der­ing cof­fee for him­self, Craw­ford, and me in his flu­ent Vi­et­namese, he talks about the trick­i­ness of the lan­guage—how “ban,” pro­nounced with al­most un-hear­able vari­ations, turns in­to a whole host of un­re­lated nouns. “That’s where you get in trouble,” he says. He asks me the ques­tion all South­ern­ers must ask each oth­er upon meet­ing: “Where you from?” And then, pleas­ant­ries over, he fixes those eyes on me and asks, with faux con­cern, “So, what are you gonna do to me?”

He knows per­fectly well what I’ve come to do—try and crack a mys­tery that’s had politicos buzz­ing with spec­u­la­tion and high hu­mor for months. Pretty much every­one had as­sumed that Webb’s brief for­ay in­to elect­or­al polit­ics was over when he stepped away from the Sen­ate in 2013. But in Septem­ber, he’d ad­dressed the Na­tion­al Press Club, lay­ing out for­eign policy and eco­nom­ic prin­ciples that soun­ded like the mak­ings of a pres­id­en­tial plat­form. Then, a couple of weeks after the Novem­ber midterms, he’d pos­ted a low-rent video—just an un­smil­ing Webb at a desk, in front of a weirdly glow­ing blue back­drop—an­noun­cing that he was ex­plor­ing a pres­id­en­tial run. Which raised nu­mer­ous ques­tions bey­ond, “Is he ser­i­ous?” To wit: How might a pot-stir­ring com­bat vet­er­an and one­time Re­agan Cab­in­et mem­ber, who com­bines Eliza­beth War­ren’s pas­sion for eco­nom­ic justice with Rand Paul’s itch to re­in­vent for­eign policy, shake up the Demo­crat­ic primar­ies? Could an icon­o­clast like Webb gal­van­ize Hil­lary-wary pro­gress­ives? And in the likely event that he ul­ti­mately lost the nom­in­a­tion to Clin­ton, how would his pres­ence in the race change the way she cam­paigned, or the way she might ul­ti­mately gov­ern?

Some pun­dits perked up at the no­tion of Clin­ton hav­ing to face a mil­it­ary hero and fiery pop­u­list; wise old Wash­ing­ton head Al Hunt wrote that Webb “could be Hil­lary Clin­ton’s worst night­mare.” Oth­ers laughed off the “ex­plor­a­tion” as a non­starter—a one-term sen­at­or who de­tests the nitty-gritty of polit­ics, and es­pe­cially fun­drais­ing, hop­ing to make a dent in the Clin­ton jug­ger­naut? Puh-leeze. The Clin­ton camp didn’t seem to be tak­ing the idea quite so lightly, though; one un­named aide mocked the cable-ac­cess look of Webb’s an­nounce­ment, dub­bing it a “14-minute host­age video,” while staffers of Clin­ton com­mu­nic­a­tions guru Phil­ippe Reines re­portedly began ply­ing re­port­ers with sa­la­cious ex­cerpts from Webb’s six nov­els.

Shortly after the video was re­leased, Webb gave a speech to journ­al­ists in Rich­mond, sound­ing every bit the can­did­ate. “The Demo­crat­ic Party has lost the mes­sage that made it such a great party for so many years,” he said. “And that mes­sage was: ‘Take care of work­ing people, take care of the people who have no voice in the cor­ridors of power.’ “

Then he went AWOL. For the next two months, he turned down nearly every in­ter­view re­quest, made (and sched­uled) no pub­lic ap­pear­ances, and spoke only, and sporad­ic­ally, through Twit­ter. The head­lines turned from “Worst Night­mare” to (lit­er­ally, on MS­N­BC), “What Is Jim Webb Do­ing?”

What he’d been do­ing, it turns out, was re­cu­per­at­ing from sur­gery and think­ing hard. “Most of these pres­id­en­tial ex­plor­a­tions are really cam­paigns,” says his long­time ad­viser and friend Dave “Mud­cat” Saun­ders. “Jim’s really ex­plor­ing, like Ponce de León and all those dudes.” Webb says he doesn’t know when he’ll make up his mind about tak­ing the plunge. (“He’ll just tell us,” Saun­ders says. “That’s the way it is.”) But he’s been en­cour­aged by the ini­tial re­sponse: no money to speak of, but thou­sands of emails ur­ging him to run, he says, and “more than 1,000 of­fers of vo­lun­teer help.” “If I had to char­ac­ter­ize the tone,” he says, “it’s this: ‘Fi­nally, we’ve got some­body who’s talk­ing straight.’ I think that’s what people are thirst­ing for.” 

IN BROAD STROKES, Webb cer­tainly looks like what the anti-Hil­lary Demo­crats are thirst­ing for: a skep­tic of mil­it­ary in­ter­ven­tion­ism, and a dyed-in the-wool cham­pi­on of the less-priv­ileged. No oth­er po­ten­tial can­did­ate in either party can of­fer the com­bin­a­tion of deep for­eign policy ex­pert­ise and anti-Wall Street fer­vor that Webb can muster—and he’s staked him­self out clearly and con­sist­ently to Clin­ton’s left in both realms.

It could be a po­tent one-two punch for 2016. Pro­gress­ives have be­come in­creas­ingly rest­less with the tri­an­gu­lat­ing “New Demo­crat” polit­ics that Hil­lary’s hus­band ushered in, and are spoil­ing for a fight over the soul of the party. If they’re to take on the es­tab­lish­ment, however, they’ll need someone to carry their mes­sage in­to battle. If the “Draft War­ren” move­ment doesn’t bring her in­to the race, the two po­ten­tial Demo­crat­ic con­tenders on Hil­lary’s left wing, Bernie Sanders and Mar­tin O’Mal­ley, both come with sig­ni­fic­ant draw­backs—Sanders’s so­cial­ism ties him per­man­ently to the fringe, and the former Mary­land gov­ernor lacks ex­per­i­ence on the na­tion­al (much less in­ter­na­tion­al) stage.

Still, if Webb hopes to lead the pop­u­list charge, he will have some woo­ing to do. The pro­gress­ives who de­cide Demo­crat­ic primar­ies have al­ways re­garded him with sus­pi­cion—and not just be­cause he’s a white, ex-mil­it­ary, South­ern male who loathes “in­terest-group polit­ics.” His dec­ades’ worth of con­tro­ver­sial op-eds and pub­lic pro­nounce­ments—which have in­cluded sharp de­nun­ci­ations of wo­men in com­bat, af­firm­at­ive ac­tion, ‘60s lib­er­als, and an­ti­war pro­test­ers—have un­der­stand­ably left them won­der­ing wheth­er he can be trus­ted. Webb’s strong suit is speak­ing to dis­af­fected white folk; he un­der­stands them in­tu­it­ively. And Webb is more sim­patico with the mod­er­ate wing of the party on mat­ters such as guns (he loves ‘em). But the is­sues that will drive Webb’s cam­paign are the ones that will drive the op­pos­i­tion to Clin­ton—mainly from the Left.

And so: no money, no or­gan­iz­a­tion, no nat­ur­al con­stitu­ency—a Webb 2016 ef­fort looks, to the con­ven­tion­ally wise, like the ul­ti­mate ex­er­cise in quix­ot­ism, something no sane politi­cian would con­sider. Which is ba­sic­ally what I ask him about over lunch: Are you still in­ter­ested in run­ning? And if so, giv­en what you’d be fa­cing, why?

Webb laughs heart­ily at the second ques­tion. “I’m a bet­ter lead­er than le­gis­lat­or,” he says. “I like to think about things and get things done. Part of it’s the writer in me, where you take a very com­plex is­sue, you break it down, and you try to come up with an­swers.

“People get sur­prised, be­cause I didn’t run for reelec­tion,” he adds. “But I’ve done this four times in my pro­fes­sion­al ca­reer, where I go in­to pub­lic ser­vice for a while and then get out. I think it’s healthy.”

What seems healthy to Webb might strike oth­ers as down­right strange, but his life’s al­ways been like that. As he re­calls in his latest mem­oir, I Heard My Coun­try Call­ing, he grew up a mil­it­ary brat in a peri­pat­et­ic Scots-Ir­ish fam­ily with roots in Ap­palachia (which he proves by pro­noun­cing “roots” as “ru-uts”) and an­ces­tral ties to the Demo­crat­ic Party. He’d planned to make his own ca­reer in the mil­it­ary, but his mul­tiple wounds made that im­possible. In the 1970s, he worked on vet­er­ans’ af­fairs on Cap­it­ol Hill for Re­pub­lic­an Rep. John Paul Ham­mer­schmidt of Arkan­sas. (After he went to work for the Re­pub­lic­an, he wrote in one of his books, “one of my fa­vor­ite great aunts, who when I was young had doted on me, would no longer even let me in­side her house.”) In the ‘80s, Webb worked in Pres­id­ent Re­agan’s Pentagon as as­sist­ant De­fense sec­ret­ary and Navy sec­ret­ary be­fore resign­ing in protest over the size of the fleet.

He’s filled the in­ter­vals mainly with journ­al­ism and writ­ing: Webb, who won an Emmy Award for re­port­ing from Beirut for PBS in the 1980s, has writ­ten six nov­els, in­clud­ing the highly ac­claimed Fields of Fire, along with three works of non­fic­tion, and the story for the film Rules of En­gage­ment. For the most part, he says with evid­ent sat­is­fac­tion, “I’ve nev­er had a salary. Everything I’ve ever done is eat or be killed.” Webb is cur­rently writ­ing and pro­du­cing the pi­lot for a “fic­tion­al series about Vi­et­nam” on the FX chan­nel, prompt­ing Craw­ford to quip, “Jim Webb’s check­list: Get ma­jor knee sur­gery, write TV series, think about run­ning for pres­id­ent.”

Craw­ford’s lit­any may soon prove one item short; if Webb’s go­ing to be vi­able, he has to stop think­ing and start mak­ing some noise. Be­cause if he pos­sesses any polit­ic­al tal­ent, it’s the one that is in­dis­pens­able for any in­sur­gent can­did­ate run­ning against long odds: an amaz­ing knack for ril­ing people up. And if he’s ser­i­ous about mak­ing a charge at the White House, he won’t sit on that skill for long.

WEBB’S FIRST EX­PER­I­MENT with gonzo cam­paign­ing was a smash­ing suc­cess—a late-start­ing, un­der­fun­ded chal­lenge to Sen. George Al­len, the pop­u­lar sen­at­or from Vir­gin­ia who was many con­ser­vat­ives’ early pick for pres­id­ent in 2008.

The Net­roots had be­gun to clam­or for a Webb cam­paign in 2005; who bet­ter to carry the anti-Bush ban­ner, after all, than a mil­it­ary hero who’d loudly and stead­fastly op­posed the war? Webb had be­gun warn­ing about the per­ils of in­vad­ing Ir­aq when he was serving as Re­agan’s Navy sec­ret­ary. In Septem­ber 2002, with Pres­id­ent Bush and Vice Pres­id­ent Dick Cheney hard-selling their war plans, he had soun­ded the alarm in The Wash­ing­ton Post, pre­dict­ing “30 to 50 years” of oc­cu­pa­tion and warn­ing that U.S. in­va­sion forces would “quickly be­come 50,000 ter­ror­ist tar­gets.” When Webb met with Al­len, whom he’d en­dorsed over Demo­crat­ic Sen. Charles Robb in 2000, to make his case against the war, he re­portedly came away dis­gus­ted with Al­len’s protest: “You’re ask­ing me to be dis­loy­al to my pres­id­ent.”

Webb says it was Bush’s re­sponse to Hur­ricane Kat­rina, in the sum­mer of 2005, that “fi­nally pushed me over” and led him to think ser­i­ously about giv­ing the Sen­ate a shot as a Demo­crat (Vir­gin­ia has no party re­gis­tra­tion, so he didn’t have to make a switch). And think he did—for months on end, driv­ing the “Draft Webb” move­ment batty. Fi­nally, well bey­ond the last reas­on­able cutoff date, he gave the word. “We didn’t start out with many ad­vant­ages,” he says, chuck­ling at the un­der­state­ment. “I an­nounced nine months out, with no money and no staff, and we were 33 points be­hind in the polls. My op­pon­ent had just got­ten the highest vote for pres­id­ent at CPAC”—the Con­ser­vat­ive Polit­ic­al Ac­tion Com­mit­tee’s an­nu­al con­fer­ence.

“I lent the cam­paign $100,000 of my own money. We were ask­ing people to take a risk. I’d nev­er run for of­fice; I was known as a com­ment­at­or. I was one of the few people who was able to write for both The Wall Street Journ­al and The New York Times. I was known as both a writer and someone who had, by that time, spent about 12 years in gov­ern­ment ser­vice.” If, that is, he was known at all.

In mid-Septem­ber 2006, soon after Webb’s cam­paign had turned in­to a sur­pris­ingly vi­able ef­fort, I rode along for a couple of days as he made his way from lib­er­al, di­verse North­ern Vir­gin­ia to the rur­al, white-and-black South­ern Vir­gin­ia hills. Only a month earli­er, Webb had been lag­ging in the polls; Al­len was out­spend­ing him 15-to-1. But over the sum­mer, the Re­pub­lic­an had let fly an odd sort of ra­cial slur—”macaca”—at a cam­paign rally, and his sub­sequent at­tempts to paint him­self as “col­or-blind” had only dug him a deep­er hole. Money had star­ted to pour in­to the Webb cam­paign, the polls had turned around, and the com­bat boots the can­did­ate wore on the trail—his son Jimmy’s, from com­bat duty in Ir­aq—were be­com­ing a na­tion­al sym­bol of res­ist­ance to the seem­ingly end­less Mideast wars. Webb was on fire.

“I think both parties have been taken over by elites,” he told me at the time, over his shoulder from the front seat of his cam­paign vehicle: a small, cam­ou­flage-pat­terned SUV with “Born Fight­ing”—the title of his 2004 his­tory of the Scots-Ir­ish in Amer­ica—em­blazoned on the side, and an old Vi­et­nam buddy, “Mac” McGar­vey, at the wheel. McGar­vey was nav­ig­at­ing us to­ward Al­ex­an­dria, where a young sen­at­or named Barack Obama was set to give his pal a rous­ing en­dorse­ment.

“The nat­ur­al base of the Demo­crat­ic Party, work­ing-class folks, looked at both parties back in the ‘80s and saw they wer­en’t go­ing to get any more help on eco­nom­ic is­sues,” Webb went on. “The one place they thought they could make a dif­fer­ence was on these di­vis­ive so­cial is­sues, so that’s how they’ve been vot­ing. But I think that has run its course now.” Later, he told me, “If we can get a num­ber of these people to come back to the Demo­crat­ic Party based on eco­nom­ic pop­u­lism and fair­ness, rather than the way they’ve been man­euvered on is­sues like flag-burn­ing, God, guts, guns, gays—if they can be reached out to with re­spect, and in terms of fun­da­ment­al fair­ness, I think a lot of them will come back to the Demo­crat­ic Party.”

Webb cam­paigns for the Sen­ate in Salem, Va., in 2006. (Charles Om­man­ney/Getty Im­ages)

But even though Webb’s an­ti­war, anti-Bush mes­sage fit the mo­ment like a glove, the cam­paign pres­aged some of the chal­lenges he might face in 2016, on a vastly lar­ger na­tion­al stage. Not sur­pris­ingly, Vir­gini­ans didn’t know quite what to make of a former Re­agan of­fi­cial who sup­por­ted abor­tion rights. Or a can­did­ate who de­nounced the war and de­cried eco­nom­ic in­equit­ies—but who also had a long, richly doc­u­mented his­tory of lib­er­al-bash­ing. His view on same-sex mar­riage, mean­while, was hard to parse: Webb op­posed it, but he also op­posed a con­sti­tu­tion­al ban that was on the Vir­gin­ia bal­lot that year.

Webb’s stub­born re­fus­al to toe any polit­ic­al or par­tis­an line some­times leaves him look­ing like a walk­ing, talk­ing hu­man con­tra­dic­tion—a qual­ity that doesn’t tend to play well in polit­ic­al cam­paigns. “Webb is of­ten cat­egor­ized as a cent­rist,” The Roan­oke Times ed­it­or­i­al­ized after his video was re­leased. “That’s not true. Webb simply does not fit neatly in­to the con­ven­tion­al, two-di­men­sion­al left-to-right uni­verse. To un­der­stand where Webb is com­ing from, you have to think in three di­men­sions, which will be his prob­lem with party act­iv­ists (and some journ­al­ists, as well).”

By 2006, Webb had long since changed his tune about wo­men in com­bat—the of­fend­ing art­icle he wrote, all-too-mem­or­ably titled “Wo­men Can’t Fight,” had been pub­lished in 1979, and he had an im­press­ive track re­cord of hir­ing and pro­mot­ing wo­men in­to com­bat roles dur­ing his Pentagon ten­ure. But the char­ac­ter­ist­ic­ally strong rhet­or­ic of the piece, when Al­len’s camp re­vived it, planted nag­ging doubts in the minds of wo­men voters, es­pe­cially. His run­ning op-ed battle against af­firm­at­ive ac­tion, and his cham­pi­on­ing of Scots-Ir­ish cul­ture and “Jack­so­ni­an demo­cracy,” had the same ef­fect on Afric­an-Amer­ic­an voters, as well as the white pro­gress­ive pro­fes­sion­als who’d flooded in­to North­ern Vir­gin­ia and turned the state purple. Webb had been es­pe­cially ef­fus­ive in a 2000 Wall Street Journ­al book re­view that was widely quoted and wondered at: “Af­firm­at­ive ac­tion, which ori­gin­ally sought to re­pair the state-in­duced dam­age to blacks from slavery and its af­ter­math, has with­in one gen­er­a­tion brought about a per­meat­ing state-sponsored ra­cism that is as odi­ous as the Jim Crow laws it sought to coun­ter­mand.”

To add to the con­fus­ing wrinkles, this “state-sponsored ra­cism” guy was the same can­did­ate who was mak­ing crim­in­al-justice re­form a cam­paign is­sue—a rar­ity in 2006—and was out on the cam­paign stump rail­ing against the over-in­car­cer­a­tion of black men and oth­ers as a “na­tion­al dis­grace.” Aside from Ir­aq, everything about Webb seemed over­com­plic­ated, im­possible to sort out and cat­egor­ize. Even his pop­u­lism had an ex­tra di­men­sion. Where John Ed­wards was preach­ing about the “Two Amer­icas,” Webb was say­ing there were ac­tu­ally three. “We’ve done a pretty good job in this coun­try in terms of the safety net for people who’ve fallen by the way­side; we’re not per­fect, but we’ve got good pro­grams,” he ex­plained to me. “The people at the very top, they’re off the charts. The chal­lenge is to make it fair for the people in the middle.”

Ul­ti­mately, the ideo­lo­gic­al puzzle that Webb presen­ted didn’t mat­ter. Vir­gini­ans may have been con­foun­ded by the born-again Demo­crat, but a vote for him was the clearest pos­sible re­jec­tion of Bush’s pres­id­ency—and Al­len, of course. Webb won nar­rowly, but his mis­sion to bring his fel­low South­ern whites back in­to the Demo­crat­ic fold had largely been a flop; where Demo­crat­ic Sen. Mark Warner’s “Bubba” cam­paign for gov­ernor had won a ma­jor­ity of whites in 2001, Webb lost them by 24 per­cent­age points—just as Obama would in the 2008 pres­id­en­tial elec­tion. Webb’s skin-of-the-teeth vic­tory had come cour­tesy of Afric­an-Amer­ic­ans, single wo­men, white pro­fes­sion­als in North­ern Vir­gin­ia, and mil­len­ni­als.

Webb “left the Sen­ate be­cause he doesn’t like the Sen­ate,” says Steve Jard­ing. “An ex­ec­ut­ive of­fice is dif­fer­ent.”

WEBB’S EN­SU­ING SIX years in the Sen­ate taught him one thing above all: He had no busi­ness be­ing in the Sen­ate. Webb had come with a repu­ta­tion in Wash­ing­ton circles—fair or not—as a tem­pes­tu­ous char­ac­ter, thanks to his resig­na­tion as Navy sec­ret­ary (in a huff, it’s said) and his star­ring role in the bit­ter de­bate over Wash­ing­ton’s Vi­et­nam Me­mori­al. (Webb hated Maya Lin’s design, call­ing it “ni­hil­ist­ic,” and led the ef­fort to in­stall a statue of three sol­diers next to the wall.) Be­fore he could even be sworn in, he was giv­ing doubters more am­muni­tion by tread­ing all over the su­per­fi­cial niceties that of­fi­cial Wash­ing­ton thrives on. In late Novem­ber 2006, ac­cord­ing to The Wash­ing­ton Post, at a White House re­cep­tion for new mem­bers of Con­gress, Webb steered no­tice­ably clear of Pres­id­ent Bush, re­fus­ing to pass through the re­cep­tion line or have a pic­ture taken with the com­mand­er in chief. When Bush tried to break the ice, ask­ing Webb, “How’s your boy?” Webb shot back: “I’d like to get them out of Ir­aq.” When the pres­id­ent tried again, Webb curtly replied, “That’s between me and my boy.”

Up­stand­ing Wash­ing­to­ni­ans like George Will were hor­ri­fied. “Webb cer­tainly has con­veyed what he is: a boor,” the colum­nist wrote, and then he offered the new sen­at­or some ad­vice: “In a re­pub­lic, people de­cline to be led by lead­ers who are in­suf­fer­ably full of them­selves.” (Later, after Jimmy Webb came home from Ir­aq, his fath­er ar­ranged for them to meet Bush at the White House as a ges­ture of re­con­cili­ation. But the loose-can­non rep was already in­delibly in­grained.)

Of course, many on the Left rel­ished Webb’s snub of the pres­id­ent. And in Janu­ary 2007, when Harry Re­id tapped the fresh­man sen­at­or to de­liv­er the Demo­crat­ic State of the Uni­on re­sponse, Webb won more ad­mirers. He’d tossed the script he was giv­en and writ­ten his own, telling Re­id, “If you want me to de­liv­er the State of the Uni­on re­sponse, you’ve got to let me write it.” The res­ult was a genu­ine rar­ity in that for­um: a mem­or­able speech.

“They wanted me to start with Ir­aq,” Webb re­calls. “But I raised eco­nom­ic in­equal­ity first.”On Janu­ary 23, 2007, with the fin­an­cial crash still 18 months away, that is­sue wasn’t high on the polit­ic­al agenda. But Webb was de­term­ined to smash through Amer­ic­ans’ com­pla­cency: “When I gradu­ated from col­lege, the av­er­age cor­por­ate CEO made 20 times what the av­er­age work­er did,” he said. “Today, it’s nearly 400 times. In oth­er words, it takes the av­er­age work­er more than a year to make the money that his or her boss makes in one day.” It was Webb’s take­down of the Bush ad­min­is­tra­tion’s war-mak­ing, however, that im­me­di­ately lif­ted him onto many Demo­crats’ list of vice pres­id­en­tial pro­spects. “We owed them our loy­alty, as Amer­ic­ans, and we gave it,” he said. “But they owed us sound judg­ment, clear think­ing, con­cern for our wel­fare, a guar­an­tee that the threat to our coun­try was equal to the price we might be called to pay in de­fend­ing it.”

Webb was already go­ing full-steam ahead on his first big le­gis­lat­ive pro­ject, an am­bi­tious new GI Bill that he had draf­ted be­fore his term began. After 16 months of wheed­ling, Webb saw his bill pass. The re­mainder of his time in the Sen­ate, however, was an ex­ten­ded ex­er­cise in frus­tra­tion. Though he voted con­sist­ently with the Demo­crats, he nev­er saw him­self as a par­tis­an—and in­de­pend­ent-spir­ited­ness has its costs in a le­gis­lat­ive body, es­pe­cially when the parties are bit­terly di­vided. After the Sen­ate ap­proved the Troubled As­set Re­lief Pro­gram bail­out, Webb tried to pick up the pop­u­list mantle and get some money back for tax­pay­ers with a fairly mod­est-sound­ing bill: a one­time wind­fall-profits tax on big Wall Street bo­nuses. “We came up with a bill which said: ‘If you were in a com­pany that got $5 mil­lion or more from TARP and you’re an ex­ec­ut­ive, you get your full com­pens­a­tion, plus the first $400,000 of your bo­nus, and after that, you split your bo­nus with the people that bailed you out.’ And people were out­raged,” he re­calls. The Demo­crat­ic lead­er­ship quietly snuffed out the meas­ure. “That’s the way it went,” he says.

And that’s the way it con­tin­ued. Early in Pres­id­ent Obama’s term, Webb says he ad­vised him strongly that mak­ing health care re­form his first great cru­sade would be a “stra­tegic mis­take”—it would cost too much in polit­ic­al cap­it­al, he said, and the eco­nomy needed full at­ten­tion. (Webb even­tu­ally voted for Obama­care, with re­ser­va­tions.) While he mostly lined up be­hind Obama’s ini­ti­at­ives, Webb again found him­self in con­flict with the pres­id­ent—and, by ex­ten­sion, with Sec­ret­ary of State Clin­ton—over the ad­min­is­tra­tion’s re­sponse to the Ar­ab Spring, par­tic­u­larly the U.S. in­volve­ment in Libya. What, he re­peatedly de­man­ded to know, was our guid­ing strategy in the Mideast?

In 1990, Webb warned against the mil­it­ary buildup in the Per­sian Gulf at a Sen­ate Armed Ser­vices Com­mit­tee hear­ing. (AP Photo/ Doug Mills)

By 2010, Webb was already think­ing about get­ting out. But first he would court a na­tion­al de­bate he’d been itch­ing to start for years. Webb had long been cit­ing stat­ist­ics about the na­tion’s in­car­cer­a­tion rate, telling every­one with­in earshot, “Either we have the most evil people on Earth liv­ing in the U.S., or we are do­ing something dra­mat­ic­ally wrong in terms of how we ap­proach the is­sue of crim­in­al justice.” In re­sponse, he in­tro­duced the Na­tion­al Crim­in­al Justice Com­mis­sion Act, which would have es­tab­lished a bi­par­tis­an com­mis­sion charged with reex­amin­ing such is­sues as the drug war and pris­on over­crowding. Its find­ings and re­com­mend­a­tions would then have been re­leased in the first com­pre­hens­ive re­port since 1965 on the state of crim­in­al justice in the United States.

At first, Webb faced skep­tic­al re­ac­tions from Re­pub­lic­ans, in par­tic­u­lar, who heard “crim­in­al-justice re­form” and thought “drug leg­al­iz­a­tion.” But after what an aide called months of “stress, in­san­ity, and gnash­ing of teeth,” Webb thought he had a sure thing. Every ma­jor na­tion­al law-en­force­ment group was be­hind the bill. Re­pub­lic­ans Lind­sey Gra­ham and Or­rin Hatch were Sen­ate co­spon­sors; the meas­ure had already passed the House, thanks in part to Re­pub­lic­an co­spon­sor Lamar Smith of Texas, on a routine voice vote. But when Re­pub­lic­ans launched a fili­buster—with Sen. Kay Bailey Hutchis­on call­ing the bill “the most massive en­croach­ment on states’ rights I have ever seen in this body”—the sup­port he had lined up evap­or­ated. The roll-call vote was 57-43, three votes shy of the su­per­ma­jor­ity needed to end the fili­buster.

The bill, as Webb saw it, had been the very mod­el of what le­gis­la­tion was sup­posed to be. He took to the Sen­ate floor to vent: “We spent more than four years reach­ing out to all sides of the philo­soph­ic­al spec­trum. We worked with lib­er­als. We worked with con­ser­vat­ives. We worked with law en­force­ment. We sought the views of many Re­pub­lic­ans. And we also worked in close co­ordin­a­tion with the oth­er body,” he said. “But let’s speak frankly, Mr. Pres­id­ent. In the af­ter­math of the 2010 elec­tions, and in an­ti­cip­a­tion of the 2012 pres­id­en­tial elec­tion, the mood in this his­tor­ic body has fre­quently be­come noth­ing short of tox­ic.”

Those wer­en’t Webb’s last words in the cham­ber, but they might as well have been. He had already de­term­ined that it was time to de­tox. “One of the things my wife and I dis­cussed was, do you really want to spend the rest of your life in the Sen­ate?” he says. “We just de­cided no.”

In­stead of run­ning for reelec­tion, Webb went off to write his latest mem­oir. His de­par­ture was widely seen as a re­jec­tion of polit­ics. But Webb’s friends and al­lies saw it dif­fer­ently: He was simply re­ject­ing the Sen­ate, and, in his words, the “or­na­ment­a­tions of polit­ics” that it re­quires. “He left the Sen­ate be­cause he doesn’t like the Sen­ate,” says Steve Jard­ing, the gregari­ous con­sult­ant and Har­vard pro­fess­or who co­dir­ec­ted Webb’s Sen­ate cam­paign. “An ex­ec­ut­ive of­fice is dif­fer­ent.”

WHEN WEBB AND and his tight-knit band of al­lies dream about 2016, their minds nat­ur­ally drift back to 2006; if one me­di­um-sized mir­acle happened, why not a huge one? But this time, while Webb still yearns to woo back dis­af­fected whites, his suc­cess in a Demo­crat­ic primary would hinge largely on his abil­ity to speak to pro­gress­ives, who are look­ing for a cham­pi­on to make the case against Hil­lary Clin­ton’s for­eign policy hawk­ish­ness and busi­ness-friendly eco­nom­ics.

That means he’d have to ex­plain to the Left far more clearly where he’s com­ing from. Jard­ing notes that Webb had a leg up in 2006 that he wouldn’t have this time: “He had an easy segue in­to the pro­gress­ive com­munity, be­cause they were op­posed to the war and his op­pos­i­tion was so unique among Demo­crat­ic lead­ers that they grav­it­ated to­ward him. This is a dif­fer­ent play­ing field now. The spot­light’s stronger, and the pro­gress­ive move­ment’s stronger. You look at the move­ment to draft Liz War­ren, I think her pro­gress­ive cre­den­tials are more burn­ished than Jim’s are at this point. The pro­gress­ive com­munity could em­brace her rather quickly. They’re go­ing to have to feel their way through Jim.”

Over lunch at the Banh Cuon Sai­gon, Webb hin­ted at how he might try to pitch his eco­nom­ic mes­sage more widely in a pres­id­en­tial run. “All the com­ments I’ve made are in­ten­ded to be in­clus­ive, not ex­clus­ive,” he said. “I think it’s im­port­ant that people un­der­stand that.” His fun­da­ment­al mes­sage about white poverty and af­firm­at­ive ac­tion, he says, is really not all that com­plic­ated: “There are people of all races and back­grounds who have sim­il­ar chal­lenges, and they should be treated sim­il­arly.” He paused, stared off in the dis­tance for a while, then wondered aloud: “Is it pos­sible to re­make the elect­or­ate along true lines of op­por­tun­ity? I tend to be­lieve [that] ap­proach is the health­i­est one for the coun­try, so we don’t have to fall back in­to these lines of people of col­or versus people who aren’t of that col­or. Whatever that means; my wife’s Asi­an, I guess she’s of col­or, but I don’t see col­or when I see my wife.”

Jim Webb, heal­er of ra­cial di­vides, fath­er of a new for­eign policy doc­trine and a new Demo­crat­ic Party? The very no­tion will strike a lot of polit­ic­al ob­serv­ers as out­land­ish. “We love mav­er­icks in this coun­try,” Jard­ing says, “but for some odd reas­on, we don’t elect them as pres­id­ent. The Amer­ic­an pub­lic gets a little nervous about people who think out of the box, and that’s his repu­ta­tion.” But could Webb put him­self in a box—or at least tune his rhet­or­ic to a fre­quency pro­gress­ives can hear? He’d have a host of di­lem­mas to sort out, Jard­ing says: “How far out do you go, how true do you stay to your­self and not risk ali­en­at­ing the base of the party? It won’t be easy to walk that line.” Know­ing the man as he does, he sounds a skep­tic­al note. “Webb’s own his­tory,” Jard­ing says, “would sug­gest that he isn’t ne­ces­sar­ily one to modi­fy to the mo­ment.”

If he were able to rein him­self in, what might a well-pack­aged Webb ac­com­plish? Jard­ing is among those who be­lieve he could make him­self the can­did­ate pro­gress­ives are wait­ing for. We may soon find out; the pace of Webb’s “ex­plor­a­tion” is pick­ing up, and the can­did­ate has swings sched­uled this spring through (you guessed it) Iowa, New Hamp­shire, and South Car­o­lina.

Partly from ne­ces­sity, Saun­ders says, “this is gonna be a dif­fer­ent kind of race”: close to the ground, re­ly­ing on small donors (“I don’t see the big banks and phar­ma­ceut­ic­als stand­ing in line to give to Jim Webb”), so­cial me­dia, and vo­lun­teers—and, most of all, on the can­did­ate’s tal­ent for rais­ing hackles and gar­ner­ing at­ten­tion. The pro­duc­tion val­ues, like those of the much-de­rided an­nounce­ment video, will prob­ably re­main low-wattage—which, if the ef­fort gen­er­ates a spark, will only en­hance Webb’s chances of mak­ing him­self the anti-Hil­lary, both in style and in sub­stance.

And a spark is all he would need to dra­mat­ic­ally change the dis­cus­sion, win or lose. If Webb gets a hear­ing—a place on de­bate stages and some trac­tion in the Twit­ter­sphere—he would most as­suredly make it count. He could give egal­it­ari­an eco­nom­ics their most thor­ough and force­ful air­ing since (shh, don’t tell him) LBJ, dis­rupt­ing Clin­ton’s fa­mil­i­ar talk about help­ing middle-class fam­il­ies and small busi­nesses, and lead­ing her in­to the thorn­i­er thick­ets of per­sist­ent poverty. On for­eign policy, says an­oth­er old friend of Webb’s, At­lantic writer and one­time Jimmy Carter speech­writer James Fal­lows, his im­pact could be even great­er: “Jim Webb could force Hil­lary Clin­ton to do something nobody else could: ex­plain her for­eign policy views and prob­ably move her to the middle” from the right. Webb, who is con­sti­tu­tion­ally un­able to aban­don a cause, would also do his damned­est to push the prob­lem of over-in­car­cer­a­tion and ex­cess­ive drug sen­ten­cing in­to the na­tion­al—or at least Demo­crat­ic—con­ver­sa­tion. Along the way, with his frank talk and mil­it­ary mien and South­ern ru-uts, he might even con­vince a few more white folk to see the Demo­crats as something oth­er than a cabal of urb­an lib­er­als who dis­dain heart­land val­ues.

That’s all without win­ning. Fal­lows be­lieves that Webb may be fated to be “a mes­sage can­did­ate, someone who runs to ad­vance an agenda more than to win,” and says, “I think he must know that at some level of his be­ing.” Wheth­er he’s aware of it or not, Webb could very well wind up the most con­sequen­tial loser in a pres­id­en­tial elec­tion in re­cent memory, simply by el­bow­ing Clin­ton to the left. “I really be­lieve that without Webb in the race, and I’ve told Jim this, there will not be a full and fair hear­ing of is­sues re­lated to the loss of the middle class and the whole eco­nom­ic-in­equal­ity is­sue,” says Nel­son Jones, a Hou­s­ton law­yer and long­time ally of Webb’s who was his vet­er­ans co­ordin­at­or in ‘06 and served as his chief coun­sel in the Sen­ate. By ham­mer­ing his mes­sage about the grow­ing di­vide between the su­per-rich and every­one else, Webb could lift the party’s soul-search­ing out of the blogs and op-ed pages and onto the na­tion­al stage.

MUD­CAT SANDERS HAS a Jim Webb story he loves to tell. Ac­tu­ally, Saun­ders—the Vir­gin­ia-based con­sult­ant and ra­con­teur who co­dir­ec­ted Webb’s 2006 cam­paign—has a bot­tom­less sup­ply of Jim Webb stor­ies he loves to tell. But this is one he told me in early Feb­ru­ary: One day, dur­ing Webb’s first year in the Sen­ate, Saun­ders got a call from his old pal Sen­ate Ma­jor­ity Lead­er Harry Re­id, whom he calls “Sen­at­or Give-‘Em Hell.”

“I can’t re­mem­ber what the is­sue was, ex­actly, but he says, ‘Can you talk to Jim and see if you can talk him in­to this? Would you mind?’ I said, ‘Sen­at­or Give-‘Em Hell, you been serving with him now for six or nine months: Do you ac­tu­ally think any­body’s do­ing to talk Jim in­to something he doesn’t want to do?’ “

Re­id paused for a long time, as Saun­ders tells it, then fi­nally said, “Well, while I got you on the phone, Mud­cat, how you do­ing?”

The mor­al of the story was clear enough: If Webb runs for pres­id­ent—and Saun­ders has been chat­ting with him reg­u­larly about the pos­sib­il­ity—he won’t be mes­sage-man­aged, and he won’t do it con­ven­tion­ally. “People talk about him not be­ing a politi­cian—well, they’re right.” Saun­ders says. “From my per­son­al per­spect­ive, I think Jim thinks polit­ics is bull­shit. He’s in­to civics. Polit­ics bore him, and it frus­trates him that it com­pletely screws up the end product of good civics. This idea that he’s not a good cam­paign­er—that’s bull­shit. Jim en­joys be­ing around people, he does. But as far as the polit­ic­al games that are played and all that, it’s like it bores him. Quite frankly, it’s like he’s above it—he’s above all this polit­ic­al non­sense and bull­shit.”

If that is how Webb views polit­ics, it could prove be­ne­fi­cial in 2016, help­ing to bol­ster his im­age as a non­ca­reer politi­cian in a field full of them. Or it could spell trouble. Rather than the hell-for-leath­er, 2006-style ad­ven­ture that Saun­ders and oth­er Webb loy­al­ists hope for, Fal­lows en­vi­sions a Webb can­did­acy—and, even more, a Webb pres­id­ency—as an­oth­er joy­less Sen­ate-style slog. “I’ve spoken with him about the pres­id­en­tial pos­sib­il­ity,” Fal­lows says. “My own view is that he has an ex­tremely re­mote chance of win­ning the nom­in­a­tion, which might be harder than win­ning a gen­er­al elec­tion, and he would prob­ably not like be­ing pres­id­ent. He found even the Sen­ate too con­fin­ing.”

Fal­lows chalks it up to Webb’s “writer’s per­son­al­ity”: “He’s a very good writer, and he’s made his liv­ing by clearly and, without trim­ming, ex­press­ing his views. That’s something you can­not do as a polit­ic­al lead­er. Your role is to keep 51 per­cent of the people with you over the long run. The more sharply you ex­press your views, the less likely 51 per­cent will agree on any­thing.” Fal­lows thinks the White House would be a miser­able place for Webb. “I found, from work­ing with Pres­id­ent Carter, that the pres­id­ent’s job, through the course of the day, al­lows vir­tu­ally zero private time and zero time for re­flec­tion. You are mak­ing im­possible de­cisions all day, the ones where the choices are bad and nobody else can make them. Plus giv­ing speeches and sign­ing things.”

But be­neath Webb’s hard out­er shell and his spiky rhet­or­ic, as Fal­lows well knows, he is at heart an in­cur­able ro­mantic with an old-school sense of pat­ri­ot­ic duty. It may sound crazy—it may be crazy—but Jim Webb seems to be­lieve he’s be­ing called to duty one last time. He wants to save Amer­ica from neo­con­ser­vat­ive for­eign policy and ra­pa­cious Wall Street greed; he wants to re­in­vent the Demo­crats as a true “people’s party”; and, as he’s tried to do for years in his con­tro­ver­sial op-eds, he wants to trans­form the way Amer­ic­ans think about race, class, and poverty.

For all his pie-in-the-sky tend­en­cies, Webb surely real­izes his chances of land­ing in the Oval Of­fice are slim, and that, if he man­aged to do so, he might be sorry. But he’s a man who faced down death in the jungle, re­peatedly—and who’s been con­sidered polit­ic­ally dead on ar­rival, too, in a race he man­aged to win. He may be en­ter­ing the cam­paign with a du­bi­ous polit­ic­al skill set, trail­ing a thou­sand red flags in his wake, but he’ll have the one as­set that makes an un­der­dog scary: a total lack of fear. “You say, this guy can’t win, Hil­lary’s in by all ac­counts, etcet­era—for most politi­cians, that ab­so­lutely mat­ters a lot,” Jard­ing says. “For Jim Webb, it doesn’t. He’s not go­ing to be in­tim­id­ated by any­thing. He re­spects Hil­lary Clin­ton. He knows this is an up­hill climb. But that’s not something he frets a lot about.”

Cor­rec­tion: The ori­gin­al ver­sion of this story in­dir­ectly quoted James Fal­lows as say­ing that Jim Webb “shouldn’t run” for pres­id­ent. The art­icle has been re­vised to ac­cur­ately re­flect what Fal­lows told the au­thor. Also, this story has been cor­rec­ted to re­flect the fact that Webb, as Navy sec­ret­ary, was not a mem­ber of Pres­id­ent Re­agam’s Cab­in­et.

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