The Dropout in your In-Box

The Weak-Willed Clinton Citizenry, Ralph Nader, Howard Dean, Slackers in a Windblown Tourist Trap, Keeping the Bastards Off the Mesa, Cherry-Flavored Skoal, Guiding National Discourse in Pajamas, Joe Trippi’s Cave, Bad News Bears, Wyoming Grandmothers, Carpal Tunnel Wrist Guards, Wisconsin Doughnuts

The Dropout in your In-Box

Mark Sundeen
Facebook icon Share via Facebook Twitter icon Share via Twitter


Before I changed American politics forever, I was a dropout. I lived in a town of five thousand in the middle of the desert. I worked summers as a backcountry guide, and in the winters I traveled and wrote. I held a masters degree and had finished a book, but sales were small, and getting published hadn’t brought fame or acclaim. But no matter: Living was cheap. I paid three hundred dollars to rent a trailer on an acre of tumbleweeds, and I had learned that by eating only beans, tortillas, tea, and honey, I could subsist on five dollars per week. Between the light workload, good weather, and swimming in the river, I was almost content.

And besides, I was taking a moral stand. Casting aside riches and ambition to dwell in the desert, I was protesting the excesses of the Clinton years. People had too much stuff. They were spoiled and pampered, the sort of weak-willed citizens who might one day let our sacred democracy drift into dictatorship. I was looking forward to a stock-market crash that would sweep the moneylenders from the temple.

Then came the 2000 election. It had been easy to ignore politics in the ’90s, especially since I didn’t have television or read a newspaper. (I considered my ignorance preferable to the propaganda peddled by networks and publishers who were, after all, puppets for bad corporations.) As far as I was concerned, both parties were corrupted by some nebulous source of evil that I called Big Money, and because Utah’s five electoral votes were guaranteed to go Republican, I cast my protest vote for Ralph Nader. It never occurred to me that George W. Bush might actually become president.

On Election Night I watched the returns with my best friend in Moab, Mathew Gross, also a published author, also a dropout. He had an encyclopedic knowledge of politics and a masters degree in environmental studies, but worked as a waiter. Since neither of us had internet service, we gathered at a friend’s house and clicked refresh on a news site. When Drudge announced that Gore had won Florida, we got in the truck and drove downtown to celebrate at the bar.

Somewhere in that five-minute drive across the autumn streets of Moab, Bush took the election. Matt and I drank glumly at the bar until it closed. We had been robbed by Big Money. We wanted a fight.

But whom could we fight? The next election was four years away. And besides, we were slackers in a windblown tourist trap. We had no political power, no connection to power, and we knew of no mechanism in the national process by which people like us could access power. Democracy didn’t work. We were shut out. Something had to be done.

About that time, a New York company announced plans to build a thousand-dollar-per-night luxury hotel on a mesa just outside of Moab. The developers were allied with rich investors and with the state of Utah, and they arrived in town with a team of powerful lawyers. They proposed million-dollar “pueblo-style villas,” here in a town where the average income was about thirty thousand dollars, and the dominant architectural form was double-wides. They would have day spas and five-star restaurants and drought-inducing golf courses. It was to be called Cloudrock, a name that dripped with fake Native American spirituality and back-to-the-earth opulence. Here was Big Money incarnate.

But this foe was not as insurmountable as the president of the United States, the Florida secretary of state, or a partisan Supreme Court. If we couldn’t keep the bastards out of Washington, well, at least we’d keep them off of the mesa. All the anger and powerlessness Matt and I felt about the election, we channeled against Cloudrock. And so began the curious odyssey that would eventually land me startlingly close to the control panel of the first insurgent political event in a generation: the presidential campaign of Howard Dean.



In a small town like Moab, Utah, the levers of power are within the grasp of just about anyone willing to reach for them. Matt and I got ourselves appointed to something called the County Board of Adjustments. No one seemed to know what the board did; it hadn’t met in years. But upon close reading of the code, Matt discovered that the Board of Adjustments existed to hear appeals of land-use code decisions. For instance: the Cloudrock decision.

We formed the Moab Citizens Alliance. We held meetings and hung fliers. We wrote letters to the editor. At the height of the MCA’s prominence, there were only about twenty actual members, but that didn’t matter. I discovered a talent. I could write political tracts quickly—in a single draft. Holed up in the office of Matt’s tiny duplex, we wrote fiery populist manifestos. My copy was bold. “Are we going to let a New York City real estate developer hike up the cost of living so that regular working people like you and me can’t afford to live here anymore?” went one of my salvos. “These developers are trying to hitch a horse to the Ritz-Carlton and call it a dude ranch.”

We were a team. Matt had the ideas, and I had the words. Our press releases were picked up by papers in Salt Lake City and Colorado. Cloudrock was mentioned unfavorably in the New York Times. Matt was interviewed on the local news. We had an audience. My vanity, wounded by the tiny readership of my book, sprang to life. We fancied ourselves like Robert Kennedy or César Chávez, standing up for the little guy, staring power in the face and giving it the finger. Grinning like young Napoleons, we locked ourselves in that office, convinced that the ideas we incubated would seed a grassroots movement and influence the minds of millions.

But the town elders did not applaud our civic enthusiasm. The Moab Citizens Alliance was roundly denounced. The editorial page of the only weekly paper called us elitist, radical, obstructionist, anti-growth, and a threat to the American way. When Matt rallied a crowd of hundreds with a rousing speech at a public meeting, the county council did not share their enthusiasm. Instead, the chairwoman gave Matt a personal scolding, and the council voted to approve Cloudrock.

We were defeated.



The placid ’90s had ended. The electorate was divided. America had been attacked. We were at war in Afghanistan, and rumbling toward Iraq. The stock market had collapsed. President Bush was dismantling decades of environmental protection.

Our defeat in Moab was mirrored nationally. Instead of fighting, Democrats were capitulating. On Election Night in 2002, Matt and I sat at the same bar, drinking the same beer, watching the same results. Too timid to either embrace or oppose the looming war, the Democrats lost seats in both the House and the Senate. I had worried that the Clinton years had made Americans too complacent to protect their democracy, and now my fears seemed to be realized.

Matt quickly moved past our Cloudrock bruises. When his term on the Board of Adjustments expired, he was not reappointed. He finally got dial-up internet, and his political passion found a new outlet: websites where political junkies stayed up all night debating. Blogs, he called them. This was the dumbest thing I had ever heard about.

“It’s about the memes,” he said.

I could think of no response.

“Memes,” he repeated. Here was a way that anyone, anywhere—people like us—could gain power, and not in some two-bit local boondoggle like Cloudrock, but in politics on a national scale. “One blogger frames a political debate, and he influences the other bloggers, who in turn influence the press, who in turn influence the masses!”

“Whatever,” I said. “No one will ever read those things.”

Even if our Cloudrock fight was lost, I wasn’t willing to quit. When someone appealed the approval to the Board of Adjustments, I was in a position to vote. I knew I couldn’t overcome the other four members, but winning wasn’t the point. I wanted to go down swinging.

The hearing arrived. I sat, for the first time, on the other side of the chamber. Now I was the one who could vote, and I relished looking down at my opponents in the galley whose only recourse was to approach the board and try to sway me. My bias was evident, and again I was denounced. Lawyers from Cloudrock and the state of Utah demanded that I recuse myself. A member of the planning commission presented a legal affidavit accusing me of conspiring with the plaintiffs. And then another board member turned to me and asked savagely:

“Are you now, or have you ever been, a member of the Moab Citizens Alliance?”

I refused to answer. I was not on trial here. My grip on power was tenuous, but I had come this far and I would be damned if I would let it go.

I cast my vote to overturn, a one-man minority, and once again Big Money steamrolled over me.



In early 2003, the blogosphere—that’s what Matt insisted on calling it—was buzzing about an unknown former governor from Vermont who had the audacity to run for president. One day Matt called me to his computer and, utilizing the day’s most cutting-edge technology, showed me a one-inch screen, in streaming video, of this stiff, pugilistic Yankee giving a speech.

“What I want to know is what in the world so many Democrats are doing supporting the president’s unilateral intervention in Iraq,” he snarled. He shook his fist. By the end his face was red and he was shouting: “I want my country back! I’m tired of being divided. I don’t want to listen to the fundamentalist preachers anymore!”

This was the first politician I had ever seen who was as pissed off as I was, and who was willing to say it. He was a fighter. I sensed two things. First, there was something to this internet, after all. It let me bypass the media and get a straight dose of politics. And second, that little man on that little screen, who didn’t even have his own website: he could alter history.

Matt was even more moved than I was. He drove to Vermont, borrowed his dad’s suit and tie, and showed up at Dean headquarters in Burlington. After a few days stuffing envelopes, he proposed to campaign manager Joe Trippi that Dean launch a blog. The rest is sort of history. Hundreds of thousands of people began reading Blog for America, the first such website by a political candidate. Using email and online fund-raising, the Dean campaign raised $819,000 in a single day, a record. Dean shot up in the polls, ahead of such establishment warhorses as John Kerry and Joe Lieberman.

I caught the bug, too. I was up in Alaska that summer, guiding a wilderness trip with teenagers. I did not sleep in a bed for two months. But whenever I got near a computer I logged on to see what Matt was up to. I even clicked the button and entered my credit card digits and with my twenty dollars made my first-ever political contribution.

Trippi made Matt Director of Internet Communications. Matt was working a hundred hours a week. He was mentioned in Time magazine, featured on television. Teresa Heinz Kerry singled out “that young man from Utah” as an example of why Dean was besting her husband in the polls. Matt wrote the blog posts and the emails that were raking in millions of dollars, but he also supervised a small staff on the web team, and as the campaign heated up, he needed help. That’s when I got the call.

“Come out to Vermont and be my writer.”

It was closest I’ve ever come to being in an episode of Mission Impossible. I got on a plane in Anchorage and moved in to an apartment in Burlington with Matt and his wife. I showed up at headquarters with a full beard, a flannel shirt, and cowboy boots. They looked at me askance. This was the guy that Matthew Gross had brought in to write the magic emails? To be the online voice of the first-ever online presidential campaign?

We on the web team were the darlings of the campaign. Our average age was twenty-seven—none of us had worked on a campaign before. But instead of the veteran operatives in Political, Finance, Field, Research, it was us rookies that Trippi sequestered in the cubicles around his office. We answered only to him. We kept odd hours, coming and going in the middle of the night, sometimes working from home, but always logging at least sixteen hours a day, seven days a week.

It was one in the morning, and the office was empty except for the web team’s lair, where we gazed at blinking screens beneath towers of pizza boxes. Trippi looked over the shoulders of Matt and me, sucking on Diet Pepsi and cherry-flavored Skoal, moaning at the progress of an email we were composing. He had set a staggering goal of $15 million to raise in the third quarter, far more than any Democrat had ever raised. Now with just days to go, we were more than $2 million short. Trippi’s eyes were puffy. His shirt was untucked. His belly was bulging.

“That’s terrible,” he said. “Is that the best you can do?”

Trippi had worked for seven presidential campaigns, from George McGovern to Ted Kennedy to Dick Gephardt. He’d never won: now he’d come out of retirement for this final hurrah. Trippi was Fagin; we were the ragged band of orphans and pickpockets. Or maybe more like it: we were the Bad News Bears. He looked over our shoulders and rubbed his eyes. No one spoke, for fear of getting yelled at.

“You guys just don’t get it,” Trippi said finally, and sulked back toward his office. “I swear to god one of these days you’re gonna make me stroke out.”

“What was he so pissed about?” someone said.

“No freakin’ clue.”

“Keep your head low so it doesn’t get chopped off.”

Five minutes later Trippi bellowed from his office: “Gross! Get in here!” Matt rushed in with a pad and pen. Listening at the door, the rest of us could hear Trippi howling like a wounded beast. Finally Matt emerged with a page of scribbles and translated it to me.

“I’ll have it first thing in the morning,” I said.

Matt jerked his thumb toward Trippi’s cave.

“You’ll have it in fifteen minutes.”

I flipped open my laptop and started writing. I believed that what we were doing was sacred. We were cutting Big Money out of politics. Instead of two-thousand-dollar-per-plate fund-raisers, or bundled corporate donations for hundreds of thousands of dollars, we were out-raising the others twenty dollars at a time. But in order to rid politics of Big Money, my job was to always—always—ask for money. Never could I write an email that simply outlined a position. Howard Dean’s idealism was grand, but it didn’t put the scare on Kerry and Lieberman and Karl Rove. Trippi had drilled it into us: without our fund-raising, we were Dennis Kucinich. So as I wrote, the only way supporters could prove their commitment to the cause was with cash. They weren’t donating. That word was stricken from my vocabulary. Instead, each time they clicked on that precious contribution link, they were joining a movement. In fifteen minutes I forwarded a draft to Matt.

Dear Friend

You are on the verge of making history. Through telephone, mail, and Internet you have brought $12.5 million to Howard Dean’s campaign to bring the people back into presidential politics. Three days from the end of the quarter, you are poised to reach the goal of $15 million.

Ever since March, when this campaign began with seven devoted workers in a three-room office, the Washington insiders have marshaled their forces to stop you from taking your country back. Sure, they want your vote—but they won’t give you a decisive role in determining the next president of the United States. Your energy, enthusiasm, and contributions over the last six months have ignited a new faith in the power of the grass roots, and shaken the foundations of establishment politics in both parties.

Click here to reclaim your democracy.

Now is the time to send an even stronger message to the DC insiders: the grass roots are deep—and permanent. We won’t be pulled out by the politics of the past, by the name-calling and infighting of career Washington insiders. You have already demonstrated that the people can hoist a rural governor from underdog to frontrunner. Now let’s send a message that the next election will not be decided by insiders, back room deals, big money, and special interests—it will be decided by you, the people.

You are unstoppable.

Click here to send a message.

And sure enough, we ended the third quarter with more cash raised than any other Democrat in history. Thousands of Americans—people like me who’d never before given a cent to the corrupt political process—were coughing up what they could afford. Hundreds sent emails, thanking us for what we were doing, sure that we were changing America for the better. A handwritten note and a hundred-dollar check arrived from a Wyoming grandmother who said she was the only liberal in her town. “Run with it,” she wrote.

During the months leading up to the Iowa caucus, I slept with my laptop beside my pillow. I woke in the middle of the night and scrolled through the blog’s comments. Matt and I would start posting first thing in the morning, before going to the office, before taking a shower, before having breakfast.

My fantasy had come true: holed up in a tiny apartment, we were wielding what felt like actual power, and influencing the masses. By this time my second book had come out, picked up a few good reviews, and sold a couple thousand copies. A couple thousand? Nuts. That many people were reading my blog posts in the first minute! We wrote them so fast to such a hungry audience that within seconds of posting we’d have dozens of comments, cheers, corrections. Every week, Dean climbed in the polls and the web traffic surged and the tech teams raced to expand the servers and build the system. We had more readers than most national newspapers. And what’s more, the press corps was reading our blog and emails. We knew it because sometimes they’d quote us directly, and other times they’d just repeat the meme we’d planted the day before. Here we were at the breakfast table, me and Matt from Moab, Utah, guiding national political discourse in our pajamas.



The campaign was taking a personal toll. Matt’s wife had gotten sick, but Matt couldn’t take time off from the campaign to take care of her, so she went to stay with her parents in North Carolina. My problems were less dire but more humiliating. I had a bad case of carpal tunnel in my wrist—the one I moused with. I was taking 2,400 milligrams of ibuprofen per day, and, just six months after climbing Alaskan peaks, I was reduced to wearing one of those reinforced medical wrist guards.

But we couldn’t rest now. The establishment was running scared. As soon as we won Iowa, the rest of the states would fall like dominoes toward the convention. One night Matt and I discussed whether, after the campaign, we’d return to our spartan lives in the desert, or if we’d move to Washington to take jobs with the Dean administration.

But then came Iowa. We didn’t just lose. We got creamed. A distant third after Kerry and Edwards. That night we went to bed proud in our defeat, and by the next morning we were the laughingstock of the nation. Every TV channel and radio station was playing Howard Dean’s concession speech. Over and over. You know the one: where he screams the names of all the states, trembling like Mussolini, then finally lets out what could only be called a yawp.

“All my work here,” Matt predicted, “will be eclipsed in history by this one speech.”

But there was still New Hampshire. Never mind the naysayers, I was dispatched to New Hampshire to report on the insuppressible momentum for Governor Dean. I blogged from rallies in Nashua and Plymouth:

The cameras are clicking from a wall of press and TV reporters, but the real excitement here is much more simple—it’s a community. A roomful of ordinary Americans, tired of being divided, tired of feeling powerless, coming together to restore our republic—to participate in our own government.…

If more than a thousand New Hampshirites come out on a subzero Sunday night to stand up with Howard Dean, imagine what we’ll do when we all stand up.

I ended with an exhortation to click here and take back your country. The money kept flowing. That momentum I was reporting—it was real!

But we didn’t win New Hampshire. The dominoes were falling in the wrong direction. And now the campaign collapsed. Trippi quit. Or maybe he was fired. It was never explained. The day after New Hampshire he said good-bye with tears in his eyes, ran a gauntlet of reporters outside the office, and drove home to Maryland. The political director quit. And then Matt gave notice on our apartment. He got in his truck and drove down to North Carolina to tend to his wife. The ship was without its captains.



Headquarters was in chaos. Desks were empty in the middle of the day. Howard Dean himself gathered us in a conference room, and tersely explained that there would be no paychecks this month. But the new campaign manager, someone none of us knew, arrived with the good news that we could still pull this one out. We’d win the next state. But we didn’t win South Carolina, or Arizona, or New Mexico, or Oklahoma, or Michigan, or Maine.

Fine. We would win Wisconsin, and after that the states would fall like dominoes.

Our supporters were turning on us. The blog in-box filled with personal and vicious accusations of incompetence, of stupidity, of betrayal. They demanded their money back. At first I responded to each email with gentle optimism—we’ll win in Wisconsin!—but finally they were too demoralizing. They hurt my wrist. I deleted them unopened.

Then I was called in to the office of the higher-ups. I’d never been called here before. Yes, they explained, we’d raised nearly $40 million, shattering political records. But we’d spent it all. In fact we’d spent more. We were in the hole. We didn’t have enough money for doughnuts and coffee on election day in Wisconsin.

“We need to raise seven hundred thousand dollars by Friday,” someone told me. “And you’re the only one who knows how to write those magic emails.”

This one wasn’t to be signed by one of the higher-ups, but by Governor Dean himself. This was his final rallying cry.

“Can you get us a draft in thirty minutes?”

I drove home, where I could concentrate. There were two problems. First, the whole thing was unethical. I’d badgered our supporters for months because I believed their contributions would restore our democracy. Now I knew they were just throwing their dollars at a lost cause. Yet if we didn’t ask for money, the press and the other candidates would know that we’d given up. And then we’d lose Wisconsin without a fight.

And here was the bigger problem: I had no idea what to say. Trippi was gone. Matt was gone. I only knew how to follow instructions.

I spent about six minutes thinking. Now I had twenty-four to write the draft. I couldn’t go on like this, telling them that the first domino was about to fall. What we needed was an ultimatum.

“The entire race has come down to this,” I began. “We must win Wisconsin.”

I omitted the flourishes and cut straight to the ask: give us fifty dollars. “All that you have worked for these past months is on the line on a single day, in a single state.” Anything less than a victory in Wisconsin, my letter threatened, “will put us out of the race.”

But by the time I returned to the office with my draft, I couldn’t find any higher-ups to approve it. It was eight o’clock. People had gone to dinner or gone home. I didn’t want to spend the whole night nursing this letter through all the appropriate channels. I wanted to go to sleep. I forwarded the draft to the tech guys.

“Make sure someone approves this before you send it out.”



My phone woke me up at 6 a.m. “Who approved your email?” someone said.

“I don’t know,” I said. “Why?”

“Look at the New York Times.

I opened my computer and my belly seized up. Headline: DEAN SAYS HE’LL QUIT IF HE DOESN’T WIN WISCONSIN. Lead: In an email addressed to his supporters, Howard Dean said last night, etc., etc. It had a finality and recklessness that you don’t hear in politics. It was something only an amateur would say.

My unedited email had been blasted out just after midnight, and the Times reporter had filed the story before most anyone else had read it. And here was the snag: among those who were not familiar with the email’s ultimatum was its ostensible author, Howard Dean himself.

Campaigning in Wisconsin, Dean was startled to learn from the New York Times that he was on the verge of quitting the race. On a conference call with HQ first thing in the morning, no one could locate anyone associated with the email. The best they could tell, some of those kids from the web team had written the thing from whole cloth and taken it upon themselves to launch it to the multitudes.

The blog was in mutiny. “Please reconsider this,” wrote one of the die-hards. “I have worked my a** off for this campaign. Don’t I deserve the opportunity to vote for the candidate I have poured untold hours of effort into?”

“People, save your money,” wrote someone else. “Invest it, instead of throwing it away on a finished campaign.”

I drove to the office like a man to the gallows. I had sunk the cause on which the hopes of millions rested. I tried to assume an attitude of penitence for the imminent violence. But I didn’t feel guilty. Instead, I was pleased with myself.

I wish I could report that my pleasure came from having done what was right. Maybe, I rationalized, I had done Howard Dean a favor. Everyone besides him knew he was through, and maybe my email was a necessary nudge toward reality. Surely I’d done right by those true believers who would have continued to pony up once a week between now and the convention, sure that if they could just believe harder and sacrifice more, eventually we could reclaim our country and the principles upon which it was founded.

No, that wasn’t the cause of this thrilling pride.

However unintentionally, I had dipped my finger in the flow of history, and watched it divert. I had tasted power. It was not power democratically earned and justly administered, that ideal in whose service I had come to Vermont. Instead it was the sheer egoism of having my will manifested simply because I said so. It was the seed of tyranny, the very thing I was fighting to defeat.

When I reached headquarters that morning, I learned that the new campaign manager had, in fact, approved my email. Any blame for its wrongness lay with him, not me. The waters of history that I thought I’d diverted—they quickly returned to their channel. In a week, Howard Dean would lose Wisconsin and quit the race, finalizing a fate that, since the Iowa debacle, had been apparent to all but the most blindly faithful.

Meanwhile, I was a hero. My email drew the required seven hundred thousand dollars in the first day—the second-biggest fund-raising day of the campaign—and eventually doubled its goal. I didn’t tell anyone at headquarters about my thrilling taste of power. I strapped on my wrist guard and returned to my cubicle, where we still had another week to save our republic, with me at the keyboard, sounding the bugle and rallying the troops.

More Reads

Ask Your Newstand Guy

Gustavo Turner


Ander Monson

Follow the Fear

Eric Spitznagel