The Guy Behind the Guy

When Democratic presidential hopeful Howard Dean threw off his jacket, rolled up his sleeves and let loose the scream heard
By Irin Carmon

When Democratic presidential hopeful Howard Dean threw off his jacket, rolled up his sleeves and let loose the scream heard across America, no one saw where the jacket landed. But Michael O’Mary ’99-’00 saw, because he was standing in the stage buffer the night Dean lost the Iowa presidential caucus, stretching his arms out to receive it.

He was there. Just as he’d been there in the parking lot in New Hampshire, chasing Dean after the candidate impulsively jumped on the back of a moving truck. In fact, there was hardly a waking moment O’Mary hadn’t spent by Dean’s side.

But nobody remembers that now, and in a way blending in has always been part of O’Mary’s job. As sometime speechwriter, advance man and travel aide for some of the biggest names in Democratic politics, he’s part of a corps of self-effacement, the anonymous suits and volunteer drudges that toil behind the candidate.

Yet few have moved up through the ranks as fast or as soon as O’Mary. The willingness to drop everything (repeatedly), having an unerring talent for being in the right place at the right time, and one or two Harvard connections were all it took. At 26, his resume glitters with names like John Kerry, Hillary Clinton, the Gores, Larry Summers and Howard Dean. His jobs have placed him in a White House wracked by the Monica Lewinsky scandal, in Nashville and Florida for the 2000 election recount disaster and in Massachusetts Hall for the fairly tempestuous beginning of the Summers presidency.

And this past year, when former Vermont governor Howard Dean fought his battle to remake the Democratic party in his image, O’Mary was at his side.

O’Mary may look and sound like a 1950s television boy next door, all grins and simple declarative sentences, but his childhood was anything but all-American. Born in Saudi Arabia to a Peruvian mother and a South Arkansan father in the oil business, he attended high school in Dubai. His brief spates in the U.S.—to visit family in the south, or after being evacuated during the first Gulf War—didn’t do much to create roots. Maybe that’s why O’Mary took so well to the campaign trail, crisscrossing an America he had yet to know as his own.

He didn’t see Boston until just before freshman week, when he arrived to do dorm crew. “My first impressions involved mopping floors and cleaning bathrooms,” he says.

One of his first-year roommates had never been out of the Eastern Standard Time zone, much to O’Mary’s shock. “When I was growing up,” he says, “three time zones seemed pretty close.”

At Harvard, O’Mary dabbled in Institute of Politics (IOP) activities and joined the Undergraduate Council (UC). While the IOP rejected him for a Director’s Internship in his first year, they didn’t forget him. A last-minute spot opened in Senator John Kerry’s office. The IOP called O’Mary for the job, and he got a taste of Washington life at the bottom of the ladder. And when he returned to Harvard the following year, he turned his focus to campus politics. UC presidential candidate Lamelle D. Rawlins ’99 chose him as her running mate.

“He tried to subvert one of our freshman year parties into a UC election stump speech,” says Pawel A. Swiatek ’99, O’Mary’s longtime college roommate. “Halfway through he started talking to people about running for UC.”

Rawlins was elected president, but voters passed on O’Mary in a rare case of splitting the ticket.

O’Mary continued with the UC even after he lost the election, but soon took on a paid administrative job at the IOP. There, then-fellow David Wilhelm, who’d been the national manager of the Clinton/Gore campaign in 1992 and went on to be the youngest person to chair the Democratic National Committee, saw something in him: a babysitter.

When O’Mary talks about his trajectory in politics, he denies being a master networker. “It wasn’t a conscious effort on my part to try to get to know people because I thought it was going to be helpful,” he says. “If I had known what I know now, I definitely would have made much more of an effort to get to know people who were coming through [at Harvard].”

But there was more going on there than childcare. O’Mary says Wilhelm encouraged him to apply to the White House internship, even making a call on his behalf. By the summer, O’Mary had been installed in the Chief of Staff’s office, where he languished in boredom.

When he applied for a transfer he experienced a scene that is likely echoed in seats of power across the country. At the table for a job interview, the nervousness clears with a magical question: what House were you in at Harvard? As O’Mary made the case for his transfer to the speechwriting office of the First Lady, the Quincy House resident faced Lissa Muscatine ’76 and June Shih ’94, and he could talk Harvard. He was in.

So O’Mary found himself in what was known as“Hillary-land,” one of few men in a female-dominated wing of the White House. A month later, a researcher left and Muscatine offered him a paid job. He grabbed the chance and took a year-long leave of absence.

O’Mary had just wrapped up his sophomore year, making him only slightly older than Chelsea Clinton, but he was researching and writing her mother’s speeches. Meanwhile, Muscatine, who went on to have a substantial role in the writing of Clinton’s bestselling memoir Living History, let him crash in a house she and her husband planned to eventually tear down. “There were delays, so I basically lived in a huge mansion by myself in Bethesda for eight months,” says O’Mary.

Inside the White House, the state of whirlwind never subsided. When Hillary Clinton addressed the World Economic Forum in Davos, Switzerland, for example, she insisted on writing the speech herself but at the last minute had an aide call the White House from Europe to unearth a half-remembered Weber quote.

“It was just after the White House library closed,” recalls O’Mary. “The aide said the first lady was going to wait up for it. I’m thinking, where on earth am I going to find this?”

Desperate, he turned to dorm-mate Stephen E. Weinberg ’99, who was a Social Studies concentrator.

“I get back from work one day and there’s a message on my answering machine saying, ‘Stephen, call me at the White House right away,’” says Weinberg. “One does not usually take long to return such a call.”

Weinberg didn’t have that book with him, launching a chain of conference calls around the country to find fellow veterans of Social Studies 10 who had Weber in tow. Says Weinberg, “I ended up standing in the back of a bookstore on a payphone, reading two pages of Max Weber over the phone to Michael in the White House and connected by satellite to one of the First Lady’s staffers in Vienna, who was writing it all down verbatim.”

But O’Mary was less lucky when the now Senator Clinton departed from the talking points he’d prepared for her when she participated in a round table with a group of Israeli and Palestinian youth. Long before administration policy had endorsed it, Clinton called for a Palestinian state, causing considerable consternation among her staff. O’Mary, as the staff contact for the event, was bombarded with calls and had to defend his innocence.

“I think I was smart enough to know that at 20 I wasn’t going to slip in a big policy change on the Middle East,” he says.

When O’Mary did return to Harvard, he kept on privileging his professional life over being a college kid. That year and the following summer, he did advance trip planning for the Gore campaign and then continued putting together New Hampshire events in his senior year.

“I didn’t write a thesis,” he says. “Because I knew I was going to get calls saying, ‘Can you go to New York, can you go to Florida?’”

Most of his friends graduated as scheduled, while O’Mary moved off-campus to live with his girlfriend, now his wife, Jessica R. Taylor ’99. When he’d bought an engagement ring for Taylor in Houston and brought it to Florida for a Tipper trip, Mrs. Gore was in on it and told stories about the Vice President proposing to her on one the bridges over the Charles.

Even at a university that teems with undergraduates playing grownup, O’Mary’s fast-track entrance into the adult world was unusual.

“I felt like I was doing very grownup stuff and I was having a great time with it,” he says. “I don’t think there was any time that I was thinking, ‘Wow, I could really be hanging out at the Fly or going to that party in Quincy house.’”

A few days after Commencement, O’Mary was on the Gore for President payroll as an advance man, plunging headlong into campaign hysteria. He led a team to draw thousands of people to Tipper Gore’s streetcar ride through New Orleans, DJed the Vice President’s floating parties down the Mississippi River, and spent hours on his cell phone procuring ingredients for a campaign treat: s’mores in ziplock bags labeled “Think s’more, vote for Gore.” He even debated the finer points of Spanish grammar with the presidential hopeful.

“He did a good job of carrying Mrs. Gore’s purse,” laughs Vanessa Flindt LaVallee, who was Tipper Gore’s trip director at the time.

After the last 72-hour stretch in Tampa with Tipper, O’Mary hopped on a plane to Boston, took a cab to Quincy House, voted and then got right back in a cab to catch his plane to Nashville. Even if a vote for Gore in Massachusetts didn’t necessarily “count,” he says, “I was not going to go through a year and a half of campaigning and not vote.”

On election night, everything converged on Nashville’s Loews Vanderbilt Plaza Hotel. O’Mary tore himself away from the room of CNN watchers to pick up more field staff from the airport. Some came off their plane cheering because the pilot had told them Florida had been called for Gore. O’Mary had to tell them it had been taken back.

After hours of confusion and conflicting reports, a crowd gathered in War Memorial Plaza to watch CNN on massive screens, and perhaps for a concession speech. They waited, soaked in the cold rain of November. “All of a sudden, the graphic on the screens just changed to Bush, President of the United States,” says O’Mary. “Everyone was crying, shouting. Nobody knew what was going on.”

Joseph N. Sanberg ’01-’02, O’Mary’s close friend and fellow Gore staffer, remembers comforting friends that had broken down. “It was a mixture of fatigue, stress, sadness,” he says. “You felt like it had all come to an end.” It hadn’t. Campaign chairman William Daley took to the stage to announce that Florida was still under dispute. Just then, as O’Mary and Sanberg remember it, the rain stopped.

“You throw everything in your being at what you’re doing, knowing that on a Tuesday in November it’ll all end and you’ll be able to sleep the next day,” says O’Mary. “For us, the next day never came.”

Sanberg and O’Mary went down to Florida, hoping to protest, but found little to do right away. Drained, they went to Disney World.

Back in Boston, Harvard had hired itself a brash new president. A. Clayton Spencer, Associate Vice President for Higher Education Policy, remembered O’Mary from his days as an undergraduate work study research assistant in the University President’s office. O’Mary took on a job for Lawrence H. Summers that hadn’t existed in Neil Rudenstine’s tenure: Special Assistant to the President.

“It was more help that I’d been in Washington than at Harvard,” says O’Mary. “It was a sense that I was someone who understood his world and yet also understood Harvard.”

O’Mary made himself an office in the basement of Massachusetts Hall by moving some file cabinets. From there he prepared the briefing books and oversaw the details for two years, through terrorist attacks, nationally publicized spats and political pronouncements.

“President Summers gave Michael a lot of responsibility and I know he really listened to him,” says former Summers chief of staff Marne Levine. “They had an ability to joke with one another. Michael had concentrated in economics so he really took the opportunity to learn from Larry. There was a mentor-mentee kind of relationship there.”

In an inscription to O’Mary, Summers was even more effusive. “Your wisdom, Diet Coke, a smile-—what more could a man want?”

Last month, when Hillary Clinton came to Boston to accept an award at the John F. Kennedy Library, she sought out some face time with O’Mary, who had done some advance for the event. Clinton hadn’t forgotten his days on her staff, and she also knew what he’d been up to more recently. She wanted O’Mary to tell her: what had gone wrong in the Dean campaign?

O’Mary’s America is mapped out by the front lines of presidential primaries, by Sheratons and situation rooms. He can recite jet plane particulars, has the phone numbers of endless political operatives stored in his Blackberry, and still has the customized nametag from his first trip on Air Force One. But he hadn’t planned on going back on the political trail—until Dean.

It began with an email over a Clinton White House alum listserve from a Dean staffer, suggesting that everyone check out the obscure former Vermont governor. O’Mary, who had applied to law school armed with a Summers recommendation letter, had every intention of starting at Boston College Law in the fall. He was only looking for a summer job.

Why Dean? It was early in the primary season, and most of America had yet to figure out who he was. The droves of acolytes grew as summer turned to fall, drawn by the image of Dean as a maverick. Though O’Mary would never be a “Deaniac”—years behind the scenes had made him wary—maybe he’d had enough of spin.

“Dean just seemed to me the only person who was saying what he thought and not just what was politically expedient,” he says.

Doing occasional advance work in New Hampshire led to a job offer to be New Hampshire trip director. Once again, he had to choose between the campaign and going back to school.

For the youthful political elite, the under-30 veterans of Clinton and Gore, the best bet to get back to the White House was, at that point, to join up with Kerry or Edwards.

But at the Dean campaign, “it was a group young, energetic, committed people who believed in what they were doing, who weren’t doing it because they wanted to go to the White House,” says O’Mary. “They were doing it because they wanted to change America.”

So he chose Dean.

By September, Dean had chosen him, too: the campaign was growing, and O’Mary got a call asking him to be the governor’s personal aide, what the press corps refer to as a “body man.”

According to Matt Vogel, a Dean press aide, the town hall events O’Mary had run in Spokane, Washington went unusually smoothly in a campaign where things often went wrong. This was not lost on Howard Dean. “It wasn’t like he said, ‘I need someone on the road with me,’” says Vogel. “He said, I want Michael O’Mary with me. I want someone who’s done this before.”

O’Mary never hesitated and the campaign started out modestly, in borrowed minivans and Motel 8s. Sure, O’Mary was in the inner circle, but being behind the scenes wasn’t always pretty.

“For the most part, it’s long plane rides, long car rides, long bus rides,” says Vogel. “You pull in and walk past the dumpster, walk up a fire escape, down a hallway full of pipes, and wait in the back kitchen—and then you go onstage. Politics is not glamorous.”

And for O’Mary, the job was full time.

“It means you’re up before the candidate, and on the other end of the day, you’re up after the candidate making sure the office knows who he called and didn’t during fundraising hour,” says Glen Johnson, the Boston Globe reporter who covered the Dean campaign.

The tasks of a body man could be menial—lugging around equipment, taking business cards and snapping photos—but they gave him nearly unlimited access to a growing phenomenon in American politics.

“O’Mary brought an extra dimension,” says Johnson. “This was a guy who’d been raised in the Middle East, educated at Harvard, and I think probably could talk policy with the Governor as well as carry his bags. I’m not saying he necessarily did, but you can never have too many smart people around any candidate.”

By most accounts, Dean trusted O’Mary absolutely. O’Mary estimates that in those months, they spent about 90% of Dean’s waking hours together. And as America discovered Howard Dean, O’Mary learned more esoteric details, such as Dean’s obsession with collecting state quarters and his fondness for a certain kind of Wisconsin root beer.

“He was probably the only person in the campaign that had an idea of what was going on from all different angles,” says Felix Schein, the MSNBC reporter on the campaign trail. “But he never betrayed what he knew at any point. He was really a rock of stability in a place where things were very chaotic and hectic.”

O’Mary is ruddy-faced, boyish and matter of fact. When it came to taking the governor through labor union rallies and hobnobs with Drew Barrymore and Jason Alexander alike, he would rest a hand on the candidate’s arm and intone, “Governor Dean, we need to go.”

“He’s not flashy. I think that’s what made him so good at it,” reflects Schein. “He wasn’t sort of a character, either. He’s steady.”

Reporters on the trail recall with varying degrees of frustration how tight-lipped he was about Dean. “He was not a resource to us at all, and that’s exactly the way he wanted it,” says Schein. Even now, O’Mary remains talkative but guarded; it’s not that he’s evasive, it’s just that he sticks to the basics. He speaks as though he sees the world in words like “fun” and “interesting.”

The Dean campaign’s gradual transition into a roaring success broke all the rules. “When I’d done trips for Al or Tipper Gore or for Hillary Clinton, the rule of thumb was, 100 people say they’re going to show up, 75 will,” says O’Mary. “If for Howard Dean 100 people said they were going to show up, you better have room for 250.”

Then there was that brief, manic period where the candidate was hailed by some as the Democratic messiah.

“He’s not so much of a natural back-slapping politician,” O’Mary says. “I think he’s more of a policy wonk. I think it surprised him. People just wanted a piece of him, they just wanted to touch him, which I think would drive anybody crazy.”

But the bubble was about to burst. O’Mary says he had his first misgivings when the entourage arrived in Iowa. “It didn’t feel tight or well organized. It always felt like we were improvising. It always felt like we were doing things that didn’t make sense from a political point of view.”

The campaign had peaked early. They suffered a barrage of negative press and attacks from other Democrats between November and January. But few were prepared for the humiliating loss of the Iowa caucuses.

When the bad news came, O’Mary was with Dean, piling into a luxury bus named Aretha, after the soul singer who had once used it. As the political consultants and managers frantically tried to figure out what Dean should say to accept his caucus defeat, O’Mary was already on the next step, pacing back and forth with his cell phone at his ear.

“My job that night was to make sure we got to New Hampshire after delivering the speech,” he says. “I was making sure the satellite uplink was ready. I was talking to our scheduling director facilitating the movement that night on the plane. All those little details had to be done.”

O’Mary is still indignant when Dean is described as angry, and says he rarely saw the former Governor lose his temper. But up there on stage that night, Dean started listing states, emitted that bellow and launched the end of his campaign.

Before the extent of the damage became clear, Dean watched himself giving the speech on TV on the campaign bus and everyone laughed. O’Mary says he came up with the line, “I’m so excited I could scream,” which Dean used on several occasions.

But humor wasn’t enough. The campaign dragged to an eventual halt in Wisconsin four weeks later. It seemed that after the promise of a new kind of politics, Dean would be relegated to the status of cautionary tale.

The morning Dean finally quit, O’Mary was awoken by John Edwards calling his cell phone, trying to get a hold of Dean. Fifteen minutes later, a John Kerry aide followed. It was over.

O’Mary still maintains that this path through politics was uncharted, that doors opened and he simply walked through them. “I’ve never actually set out to get a specific role in politics, and that’s actually served me very well,” he says. “I’ve been extraordinarily lucky and fortunate…my experience has been that if you do a good job and you know people, eventually they’ll ask you do something and it may become something good.”

Despite his insider knowledge, he has no intention of running for office. For one thing, he was born in Saudi Arabia, which these days does not endear a candidate to voters. Plus he has no real home base from which to run. For another, he likes being out of the spotlight.

“I’ve seen it up close,” he says, “and I’d rather be the guy behind the guy in politics than doing it myself.”

Would anything—say, a Kerry win— make him come out of hibernation after he starts law school in the fall? He won’t rule it out.