Herding Donkeys: The Fight to Rebuild the Democratic Party and Reshape American Politicsby Ari Berman
After the 2004 election, the Republican Party held the White House, both houses of Congress, twenty-eight governorships, and a majority of state legislatures. One-party rule, it seemed, was here to stay.
Herding Donkeys tells the improbable tale of the grassroots resurgence that transformed the Democratic Party from a lonely minority to a sizable/i>/p>… See more details below
After the 2004 election, the Republican Party held the White House, both houses of Congress, twenty-eight governorships, and a majority of state legislatures. One-party rule, it seemed, was here to stay.
Herding Donkeys tells the improbable tale of the grassroots resurgence that transformed the Democratic Party from a lonely minority to a sizable majority. It chronicles the inside story of Howard Dean's visionary yet deeply controversial fifty-state strategy, charting his unpredictable journey from insurgent presidential candidate, to front-running flameout, to chairman and conscience of the Democratic Party in an unexpected third act. Ari Berman reveals how the Obama campaign built upon Dean's strategy when others ridiculed it, expanding the ranks of the party and ultimately laying the groundwork for Obama's historic electoral victorybut also sowing the seeds of dissent that would lead to legislative stalemate and intraparty strife.
Revelatory and entertaining, in the vein of Timothy Crouse's The Boys on the Bus and Rick Perlstein's Nixonland, Herding Donkeys combines fresh reportage with a rich and colorful cast of characters. It captures the untold stories of the people and places that reshaped the electoral map, painting a vivid portrait of a shifting country while dissecting the possibility and peril of a new era in American politics.
“Lively [and] instructive, in some ways especially now.” —The New York Review of Books
“Wonderful…reads like a scene out of the next The Social Network.” —The Huffington Post
“Berman’s book is the Howard Zinn version [of the Democratic comeback], the story of the people who were pushed out of the frame.” —David Weigel, Slate
“An excellent account of the rise and fall of Obama’s organizing efforts.” —The New Republic
“The resurgence of the Democratic Party in the past two election cycles is one of the most important—and least understood—political stories of the new century. Ari Berman tells that tale with reportorial verve, a keen eye, a sharp pen, and a wealth of fresh insight. If you want to understand the grassroots revival of progressivism in America, and also the new challenges and aching disappointments that have come along with it, this is the book to read.” —John Heilemann, national political columnist for New York magazine and coauthor of Game Change: Obama and the Clintons, McCain and Palin, and the Race of Lifetime
“Ari Berman has written a political narrative so revelatory and exhilarating it kept me up nights reading. Herding Donkeys is some of the freshest and incisive political reporting out there, and Berman, who has the keen eye of a novelist, is one heck of a storyteller.” —Alex Kotlowitz, author of There Are No Children Here: The Story of Two Boys Growing Up in the Other America
“Herding Donkeys is essential to understanding how the Democratic Party came back from the dead in 2006 and 2008. But it’s especially good at explaining what happened to all of Barack Obama’s grassroots energy. This is a hopeful but also sobering tale, told with strong inside reporting.” —Jonathan Alter, author of The Promise: President Obama, Year One
“Herding Donkeys is political reporting at its finest. In his spirited debut, Ari Berman takes readers inside the back rooms and living rooms where politics actually happens, but his novel vantage point doesn’t prevent him from rendering the tough but fair judgments every great political reporter needs to make. This is a ripping account of the Democratic Party through an intense period of historic transformation.” —Michael Tomasky, author of Hillary’s Turn: Inside Her Improbable, Victorious Senate Campaign
“An intriguing behind-the-scenes look at how the Obama campaign built on the grassroots movement that had catapulted Dean to prominence. . . . Engaging and balanced—a stand-out book.” —Kirkus Reviews (starred review)
“With a keen appreciation of political strategy as well as an eye for telling anecdote and amusing detail, Ari Berman tells the amazing story of the Democratic party’s revival. Berman’s reporting vindicates the fifty-state strategy of Howard Dean and the determined organizing of Barack Obama—and shows why grassroots activism is still the most potent force for change in America.” —Joe Conason, author of Big Lies: The Right-Wing Propaganda Machine and How It Distorts the Truth
“Ari Berman tells the rollicking and rousing story of the fight for the soul of the Democratic party that has reshaped American politics. Full of riveting revelations, vivid reporting, and a cast of colorful characters, Herding Donkeys captures the exhilaration of the grassroots insurgency that Howard Dean launched—and Obama seized—to realign our political map. At a time of disillusionment with establishment politics, this book is solace for the soul. It is a timely reminder that the grit of tenacious organizers and antiestablishment politicians in red, blue, and purple states alike offers Hope 2.0.” —Katrina vanden Heuvel, Editor and Publisher, The Nation
"While a scoop-rich tome like John Heilemann and Mark Halperin's Game Change can tell us a lot about how campaigns are won and lost from the top down, Berman's more thoughtful book is equally good fun in telling the story of the election from the bottom up." —Dana Goldstein, The American Prospect
Herding Donkeys is a well-reported tour de force.
Lively [and] instructive, in some ways especially now.
Wonderful…reads like a scene out of the next The Social Network.
Berman's book is the Howard Zinn version [of the Democratic comeback], the story of the people who were pushed out of the frame.
An excellent account of the rise and fall of Obama's organizing efforts.
The resurgence of the Democratic Party in the past two election cycles is one of the most important--and least understood--political stories of the new century. Ari Berman tells that tale with reportorial verve, a keen eye, a sharp pen, and a wealth of fresh insight. If you want to understand the grassroots revival of progressivism in America, and also the new challenges and aching disappointments that have come along with it, this is the book to read.
Ari Berman has written a political narrative so revelatory and exhilarating it kept me up nights reading. Herding Donkeys is some of the freshest and incisive political reporting out there, and Berman, who has the keen eye of a novelist, is one heck of a storyteller.
Herding Donkeys is essential to understanding how the Democratic Party came back from the dead in 2006 and 2008. But it's especially good at explaining what happened to all of Barack Obama's grassroots energy. This is a hopeful but also sobering tale, told with strong inside reporting.
Herding Donkeys is political reporting at its finest. In his spirited debut, Ari Berman takes readers inside the back rooms and living rooms where politics actually happens, but his novel vantage point doesn't prevent him from rendering the tough but fair judgments every great political reporter needs to make. This is a ripping account of the Democratic Party through an intense period of historic transformation.
With a keen appreciation of political strategy as well as an eye for telling anecdote and amusing detail, Ari Berman tells the amazing story of the Democratic party's revival. Berman's reporting vindicates the fifty-state strategy of Howard Dean and the determined organizing of Barack Obama--and shows why grassroots activism is still the most potent force for change in America.
Ari Berman tells the rollicking and rousing story of the fight for the soul of the Democratic party that has reshaped American politics. Full of riveting revelations, vivid reporting, and a cast of colorful characters, Herding Donkeys captures the exhilaration of the grassroots insurgency that Howard Dean launched--and Obama seized--to realign our political map. At a time of disillusionment with establishment politics, this book is solace for the soul. It is a timely reminder that the grit of tenacious organizers and antiestablishment politicians in red, blue, and purple states alike offers Hope 2.0.
While a scoop-rich tome like John Heilemann and Mark Halperin's Game Change can tell us a lot about how campaigns are won and lost from the top down, Berman's more thoughtful book is equally good fun in telling the story of the election from the bottom up.
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Read an Excerpt
1 INSURGENT VS. ESTABLISHMENT
I was the biggest insult you could have—an outside-the-Beltway guy who didn’t
want to play by the Washington rules. —Howard Dean
It was one of those expansively clear summer days in the Mountain West. On August 23, 2003, Howard Dean’s campaign had just embarked on the frenetic Sleepless Summer Tour—ten cities in four days across 6,147 miles, raising a quick million via its campaign blog in the process. You could watch the dollar amount inch upward in real time on a giant baseball bat posted on the website. Dean had kicked the tour off in Falls Church, Virginia, then flew to Milwaukee. That morning he was headed to Portland, followed by Seattle, Spokane, San Antonio, Austin, Chicago, and ultimately concluding in New York City’s Bryant Park. In between Milwaukee and Seattle, the campaign added an unannounced stop in the most seemingly impractical of places—Boise, Idaho.
Idaho didn’t get a whole lot of visitors from national Democrats, except maybe for trips to their ski chalets and summer homes (John Kerry had one in Ketchum). “Let It Be Perpetual”—the state’s motto—might as well have described the Republican control of government there. So when a few local Democrats in Boise requested some face time with the former Vermont governor, they didn’t expect to get an affirmative reply. But Dean unexpectedly said yes, as he was prone to do with these types of requests. After much internal wrangling among his staff, the campaign figured it needed a refueling stop anyway, so what the hell? Let’s go to Boise!
As Dean’s chartered Boeing 737, otherwise known as the Grass-roots Express, took off from Milwaukee, his press aide, Matt Vogel, announced the stop. The campaign was going to deplane for an hour in Boise and was expecting “fifty people or so,” Vogel said. When Dean landed on the tarmac, 450 people were waiting to greet him, holding blue DEAN FOR AMERICA signs. A social worker named Delmar Stone could barely contain his exuberance. “The last time I was this excited about someone who could change the world,” Stone said, “was when I heard about Jesus!”
Dean was not quite the Messiah, but he had been on quite a roll. He’d just graced the covers of Time and Newsweek and would soon shatter Bill Clinton’s three-month fund-raising record by amassing an army of small donors over the Internet, using that money to air TV ads in six states a full five months before voters in Iowa went to their first-in-the-nation caucus. He now led in polls in Iowa and New Hampshire and had staff on the ground in twelve states and volunteers in all fifty. Assembling this kind of organization by August, said Dean’s media consultant Steve McMahon, was “unprecedented. It’s never even been contemplated.” Dean’s mad-scientist campaign guru, Joe Trippi, dubbed it “a frickin’ revolution.” Boise was living proof. If the campaign could draw hundreds of people for an unannounced stop in the Republican hinterlands, the possibilities were endless. By discarding the old plabook, Dean had become a new type of candidate, running a different kind of campaign.
Dean stood onstage behind a large American flag perched on a hangar. The five-foot-eight, 180-pound Vermonter, who was often described as “sartorially challenged,” wore a blue and white seersucker shirt with the sleeves rolled up (it gave him a salt-of-the-earth look), dotted red tie, and black chino pants, held tight by his late brother Charlie’s black and silver rivet belt, which he wore every day. (In 1973, twenty-four-year-old Charlie, the most likely politician in the Dean family, traveled to war-torn Southeast Asia and never came back, killed by guerrilla captors in Laos.) Next to Dean onstage rested another flag. “You see this flag?” he asked, grabbing it for emphasis. “This flag does not belong to John Ashcroft and the right wing of the Republican Party! This flag belongs to the people of the United States of America,” he said sternly, with more than a tinge of anger in his gravelly voice, “and we’re gonna take it back!” As it happened, Attorney General Ashcroft was scheduled to be in Boise the very next day, defending the controversial Patriot Act, which nearly every Democrat in Congress blindly went along with in the aftermath of 9/11, one of a series of capitulations to President Bush that Dean and his followers deemed unforgivable. The crowd loved Dean’s fiery rhetoric and plainspoken populism, especially when he asked, “When are Democrats going to stand up and be Democrats again?”
At the end of the impromptu rally, Dean promised to return to Idaho as soon as he could. Indeed, he went back two months later during another swing through the West, prompting a local columnist to joke that he must have a girlfriend in town, he visited so much. There was some logic to the Boise visit—Idaho would hold its caucus between the Wisconsin primary on February 17 and a glut of nine primaries on March 2, and Dean was already preparing for a lengthy primary. But the larger meaning was symbolic, a message to fellow Democrats not to take anything for granted, for Dean’s campaign—thanks to its grassroots support—could go anywhere, at any time, and leave its imprint.
A Democrat hadn’t held a major statewide office in Idaho since 1994, the year Republicans took over everything. The last man to do so, former governor Cecil Andrus, happened to be in the crowd that day. “I’ve never seen this kind of energy in Boise,” the seventy-two-year-old Andrus told Dean’s adman, Mark Squier. A careful student of political imagery, Squier watched the scene with amazement. “There’s a bunch of old-timers in the crowd,” Squier reported to Trippi, “and they’re going, Finally!” Squier punched his fist in the air to capture the intensity of the moment. “A Democrat who’s not afraid to grab the flag and stick it in the ground . . . It’s like they’ve been dying twenty years in the desert looking for someone that they can beat back with.” Such experiences drove home Dean’s conviction that there were Democrats everywhere, in the reddest of so-called red America, and that it was time for the national party to stop pretending they didn’t exist.
Twice a year, the various members of the Democratic Party—state party leaders, representatives from the different interest groups, elder statesmen—gather for the biannual meeting of the Democratic National Committee (DNC) in Washington. During the election season, the Democratic candidates for president are invited to speak. These functions tend to be polite, sterile, scripted, backslapping affairs. That wasn’t what Dean had in mind when he arrived at the podium on the afternoon of February 21, 2003.
Just a few weeks earlier, Colin Powell had gone before the UN and made what many pundits and politicians deemed to be an unassailable case that Saddam Hussein possessed weapons of mass destruction and needed to be forcibly disarmed. But Dean still wasn’t convinced, and he was increasingly agitated by the unwillingness of Democratic leaders in Congress and on the campaign trail to question the Bush administration’s march to war—and the broader failure of Democrats to challenge Bush on the domestic front. “The Democrats were shell-shocked, they were behaving like Republicans, they were afraid of their own shadow,” Dean said of the mood at the time. “And the Democratic public really wanted something different.” But he hadn’t yet articulated precisely those sentiments, and no one really knew who he was. In January 2003, Dean still had only $157,000 in the bank and seven staffers crammed into a tiny office (the kitchen doubled as a conference room) above a pub in Burlington. Al Sharpton was leading him in the polls, to say nothing of John Kerry, John Edwards, Dick Gephardt, and Joe Lieberman.
At 10:45 a.m., Dean sat in his hotel room at the Hyatt Regency on Capitol Hill. He’d just gotten off a red-eye (his preferred mode of travel) from California and was operating on two hours of sleep, which even for a doctor/politician was pushing it. He was due to speak at 11:15 and hadn’t yet prepared a speech. “So what do I have to say?” he asked his small group of advisers—media consultant Steve McMahon, then-campaign manager Rick Ridder, longtime aide Kate O’Connor. McMahon brought along his business partner, Joe Trippi, to feel out the candidate that day. Dean had met Trippi only a handful of times but knew of his reputation as a bit of a loose cannon, wildly inventive but deeply insecure and difficult to control. Trippi urged the candidate to pose a series of rhetorical questions about the decaying state of the Democratic Party. “Let’s take it to them,” Trippi said.
“This is a little incendiary for Capitol Hill,” Ridder said worriedly.
“We need to push the button now to create the movement,” Trippi responded.
“Movements don’t win elections,” Ridder said, “candidates do.”
“This will create a buzz,” McMahon chimed in, “but is it the buzz we need now?”
Dean, ever the pugilist, liked Trippi’s idea. “Let’s just draw the contrast,” he said.
Trippi wanted him to say “What the fuck happened to the Democratic Party?”
Dean knew he couldn’t be quite so explicit. “How about if I say, ‘What I want to know is’?” Dean pulled an envelope out of his pocket, kneeled down in front of a coffee table, and scribbled a litany of one-word indictments. The entire speech, if you could call it that, was hatched in ten minutes. “There was a dynamic tension in the room,” said Dean’s campaign chairman, Steve Grossman, “that led me to believe that Howard had something he needed to say to the DNC, to the American people, to the media, and he knew this was the moment.” But as was so often the case, nobody quite knew exactly what shoot-from-the-hip-Howard would say once he took the stage.
His staff had passed out little packages of Vermont maple syrup and cheddar cheese as goody baskets, so Dean started the speech with a line thanking his campaign team for its hard work. Then he paused, licked his upper lip, and got right to the point.
“What I want to know,” he said in a deadly serious monotone, “is why in the world the Democratic Party leadership is supporting the president’s unilateral attack on Iraq.” So much for a formal introduction. Scattered cheers came from a group of supporters holding white Dean signs in the back of the room.
Usually, political speeches take a while to get going, but Dean chose not to bury the lede, as they say in the news business, and continued his refrain. “What I want to know is why are Democratic Party leaders supporting tax cuts? The question is not how big the tax cut should be, the question should be can we afford a tax cut at all with the largest deficit in the history of this country?” A few more isolated cheers. Most members of the audience sat uncomfortably in their seats.
“What I want to know is why we’re fighting in Congress about the Patient’s Bill of Rights when the Democratic Party ought to be standing up for health care for every single American man, woman, and child in this country.” More nervous clapping and scattered cheers.
“What I want to know is why our folks are voting for the president’s No Child Left Behind bill that leaves every child behind, every teacher behind, every school board behind, and every property tax payer behind.” Dean was picking up steam, and amid a few more hoots and hollers people were starting to stand up and get in on the act. He waited for a moment, then delivered the punch line he’d unknowingly borrowed from the late senator Paul Wellstone, who was killed in a plane crash days before the election in October 2002.
“I’m Howard Dean,” he told the room, “and I’m here to represent the Democratic wing of the Democratic Party!” The room finally exploded, with more than one person asking themselves, “Who is this guy?!”
Steve Grossman led the DNC from 1997 to 1999 and had sat through more than a few of these gatherings. He’d never seen one like this before. “The response to all of the candidates was rather tepid, but people flew out of their seats for Howard,” he said. “The applause was thunderous.” Grossman sensed immediately the larger significance of the speech. “He challenged the Democratic Party right to its core,” Grossman said. “To some extent he was challenging the people in the room, but they didn’t see it that way, because they were always chafing under party orthodoxy and many of them were grassroots activists and they were looking for somebody to galvanize them and pull them out of that morass.” Dean emerged the clear winner of the early cattle call. “He just blew those people away,” said Joe Klein of Time magazine. “It was one of the most effective speeches I’ve ever seen a candidate give.” The question was, would it be a temporary blip or the beginning of something bigger?
The Dean offensive had begun. For Trippi, “it was sort of like love at first sight,” he recalled. Soon after, he went up to Burlington to run the campaign full-time. He and Dean proved a combustible mix, like throwing vinegar on baking soda in chemistry class. “There’s an unpredictability about Howard Dean that’s mirrored by the unpredictability of Joe Trippi,” Grossman said. “You never knew on any given day exactly how it was going to turn out.” Dean’s speech on February 21 marked the beginning of that wild ride, which would continue long after his presidential campaign came crashing apart.
“My goal was not to be the best friend of all the people I was running against,” Dean said. “My goal was to win. And I thought the party wasn’t going to win unless we underwent fundamental change.” His DNC speech, more than any other single event, set the tone for the rest of the campaign and shifted the arc of the Democratic Party for years to come. What direction the party would take, however, was hardly a settled question. Could Democrats once again become a party of the people, motivated by core principles and powered by grassroots activists out in the states? Or would the party remain a Washington-centric institution, plagued by caution and calculation and dominated by a privileged group of megadonors and political operatives? In the weeks and months and years that followed, Dean would become a folk hero to insurgent Democrats across the country, but also a marked man among a circle of increasingly discredited yet stubbornly unyielding power brokers eager to hold on to their turf. The fight was much bigger than one person; Dean was only the match that lit the fire.
A year and a half earlier, Dean strolled into the office of his top aide, Kate O’Connor, a thin, wiry, meticulous thirty-seven-year-old native Vermonter, and casually told her he was planning to run for president. She barely blinked. “If George Bush can do it,” O’Connor told her boss, “then why can’t you?”
In presidential politics, there are really only two types of characters worth paying attention to: the establishment candidates and the insurgents. Those in the former club rely on their lifetime of experience, well-to-do friends, media connections, and influential circle of advisers to bulldoze over their lesser opponents. The British writer Henry Fairlie, in 1955, famously described “the Establishment” as “the whole matrix of official and social relations within which power is exercised.” Despite claims to the contrary, such an establishment most certainly still exists.
Insurgents, by contrast, possess none of these claims to power and usually start off broke and unknown. They must create buzz—usually by saying something unusually substantive for a politician that is counter to the position of the establishment candidate(s)—to get in the papers, which they hope will help them raise money. From the very beginning Dean was, by default, an insurgent. He hardly visited Washington, spent little if any time socializing with the political and media in crowd, and had never raised more than $1 million for any of his campaigns. “I’m going to be dead last in fundraising,” Dean predicted early on. He liked to be home on weeknights and in Burlington on weekends. Though he was happily married, his wife, Judy, a practicing physician, hardly ever campaigned with him, which had to be a first for any presidential candidate. Nor did she upgrade to cable television in order to follow the campaign from afar. Dean’s own mother, an art appraiser in Manhattan, described his campaign effort as “preposterous, and besides, it’s very expensive.”
True, Howard Brush Dean III wasn’t exactly a stranger to high society. His relatives came over on the Mayflower and hunted whales off of eastern Long Island. He’d grown up on Park Avenue in Manhattan, descended from a long lineage of Republican bond traders (his great-grandfather was a managing partner at Smith Barney), spent summers in the Hamptons (where his dominating father, Big Howard, played golf at the exclusive Maidstone Club), and attended a Waspy boarding school in Rhode Island and then Yale. Dean’s grandmother asked Dorothy Wear Walker Bush, future grandmother to George W., to be a bridesmaid at her wedding. But after an uninspired stint at the white-shoe trading house Clark Dodge, Dean eschewed the stuffy corporate existence by moving to Vermont for his medical residency in 1978, taking up stock in the Green Mountain State. His neighbor Esther Sorrell happened to be the grande dame of the Vermont Democratic Party, which is how Dean got his start in the business, serving as a local precinct captain and rising through the ranks. A friend described him as “a member of the club with a strong fuck-you mentality.”
Temperamentally, Dean was certainly more suited to the insurgent variety—frank, flinty, allergic to staying on script. He was the kind of guy who, though he could afford far better, drove a blue Chevy Malibu, rode a thirty-year-old mountain bike that his wife joked he’d bought for $10 at a garage sale, and painted his own house for relaxation, sometimes mixing paints to save money. His political consultant Steve McMahon recalled, upon first meeting him in 1992, that Dean was “remarkably and refreshingly honest and candid, and not a very snappy dresser. He didn’t really fit the stereotype of a politician as much as he fit the stereotype of a doctor.”
Dean knew he’d be an underdog if he ran, and circumstances gave him little choice in the matter. He’d thought about running for president in 2000, but Al Gore put the kibosh on that one. Since then, he’d had some time to think about the matter, and knew full well the odds were steep and slanted. Only one insurgent candidate had captured his party’s nomination and gone on to win the presidency in the past quarter century, and that was Jimmy Carter in 1976. As it happened, Dean had volunteered for Carter’s campaigns in 1976 and 1980, and knew a thing or two about the man. He flew down to Georgia and consulted the former peanut farmer turned president, receiving what, by this time, could be considered predictable advice: go to Iowa.
It was Carter who put the Iowa caucus on the map, and that initial victory gave his campaign the instant credibility, money, and staff it so desperately needed. Dean knew that if he just did well enough in Iowa, he’d be in good shape in New Hampshire, where voters next door knew him. From then on, he reasoned, he could win a war of attrition against his opponents, competing in every state and going all the way to the convention if need be. He’d drive to every state himself if it came to that or fly cheaply on his favorite airline, Southwest, whose travel schedule he’d memorized.
Dean began the journey by following Carter’s trail to the Hawkeye State. His closest confidante, Kate O’Connor, would also make the trip. They’d attend fund-raisers for local candidates, drop by a dinner for a county Democratic Party, meet with farmers and businessmen, try to do an interview or two with a small newspaper or radio host. “Who are you and why are you here?” would be the most common responses. To say they were winging it would’ve been an understatement. “We would go to Iowa and we wouldn’t know anybody,” O’Connor said. “People really did think we were insane.”
Dean’s travel habits were suited to life on the road; he packed sparsely, with a small carry-on bag, and, like Carter, stayed in supporters’ houses, both to get to know the locals and to save money. If he had supporters in a given town, that is. At the time a lifelong technophobe, Dean eschewed a laptop or BlackBerry for a clunky cell phone, whose voice mail he sometimes had trouble accessing. Just like Carter, Dean stressed his distance from Washington and his record as governor—he’d balanced budgets in Vermont, given kids health care, and shifted the tax burden from poorer towns to wealthier ones in order to build better schools. What had his opponents done while Rome burned? Unlike his inside-the-Beltway competitors, Dean was sensible, honest, pragmatic. He wanted, he said, to be the candidate for “moderate Democrats, moderate Republicans and Independents,” like John McCain in 2000.
In those early days, Dean was entirely unprepared for what would come next. Everybody was.
Everybody, perhaps, except for Trippi. He’d been dreaming up a radical campaign like this for a million years and was compelled to spread the news to anyone who would listen. Most chose to ignore him, as you would a crazy man on the corner ranting about the end-time. In a world of dapper political consultants, Trippi styled himself as a hopelessly shabby Don Quixote. Vermont congressman Peter Welch, who hosted the first strategy session for Dean at his apartment in Burlington, described Trippi as “the weirdest guy I’ve ever met in my life.” While everyone else drank coffee and orange juice that morning, Trippi dipped on a can of Skoal and consumed what must have been a case of Diet Pepsi—a staple of any workday for him, Dean staffers soon learned.
Trippi loved romantic losers, quoted films about hapless underdogs, and, every four years, caught presidential fever like few in the business. He was there for Ted Kennedy in 1980 and Walter Mondale in 1984 and Gary Hart and Dick Gephardt in 1988 and Jerry Brown in 1992, when Governor Moonbeam raised $5 million in three weeks in $100 increments via an 800 number in a last-ditch effort to stop Bill Clinton. Time called it “the Touch-Tone Rebellion,” led by “Public Enemy No. 1 for Establishment Democrats.”
In the 1990s, Trippi decamped to Silicon Valley and advised start-up tech companies, which opened his eyes to the possibility of using the Internet and technology to democratize politics. Meanwhile, back in Washington, Newt Gingrich and his band of suburban culture warriors grabbed the insurgent mantle, and Clinton spent the bulk of his eight years in office fighting for survival. The 1990s were not a good time for anti-establishment Democrats. In order to stay afloat and moderate the Democratic brand, Clinton cut deals with the Republican opposition on issues like taxes and welfare reform—a hallmark of his “Third Way” strategy of triangulation—invited wealthy businessmen to sleepovers in the Lincoln Bedroom to raise money, and brought in the widely reviled hatchet man Dick Morris to direct his reelection campaign. Clinton proved that he was a “different kind of Democrat,” not like those tax-and-spend New Deal liberals—but at what cost? Clinton skillfully won two presidential elections, largely due to his own personal charisma, but his party shrank during his tenure in office, losing congressional seats, governors’ offices, and state legislatures. After Clinton’s election, Democrats controlled 57 seats in the Senate, 258 seats in the House, and 30 governorships. When he left office in January 2001, Democrats found themselves a lonely minority, holding 50 seats in the Senate, 212 in the House, and only 19 governorships.
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