One vote at a time: Meet 2020’s most determined underdog

It is 6:30 a.m. and Adm. Joe Sestak is already two hours into a grueling day as he sets off down a dirt road in the New Hampshire wilds, the full moon casting a shadow ahead of him.

Stuffed in the back pocket of his jeans is his schedule – 10 events, ending around midnight – and talking points for short videos he plans to make for Instagram.

If you’re not one of his 798 followers, you may not know that Admiral Sestak is running for president. So, in a bid to garner attention, he is walking across New Hampshire. His lean new ground campaign involves hiking boots, iPhones and some assorted wires, and a single sign on a wooden stake that says, Admiral Joe Sestak for President. The admiral prefers not to carry it.

It can be lonely at the back of the 2020 Democratic pack, especially when you have a herd of senators and governors competing for ink and airtime. Many of them have struggled to get out of the single digits in polls, despite having far more funding and name recognition than the admiral.

He once commanded an aircraft carrier battle group with more than 15,000 sailors, but on his current shoestring budget he’s operating with a Ford F-150 and a crew of two. In the most recent fundraising quarter, he raised $374,000 to Bernie Sanders’ $25 million. In most polls, he registers at 0% (though there’s one that puts him at 1%, tied with Sen. Cory Booker and Rep. Tulsi Gabbard). His de facto campaign headquarters is an Econo Lodge under construction in Des Moines, Iowa, where his “admiral suite” costs less than $50 a night. The largest audience he’ll have all day, apart from a school event, is around two dozen.

All of which begs the question – why would a retired two-star admiral who worked in the Clinton White House, held senior positions at the Pentagon, and served two terms as a U.S. congressman from Pennsylvania submit himself to such, well, humiliation?

The short answer may be: he doesn’t see it that way. He loves this, he says, and thrives on talking to average Americans. And he has made a career – a life, even – of challenging seemingly insurmountable odds. His teenage daughter beat brain cancer – twice. He was elected as a Democrat in a 2:1 Republican district, and won again two years later by a landslide. He challenged the Democratic establishment and President Barack Obama after the party endorsed former Pennsylvania Sen. Arlen Specter, running against their wishes and winning the nomination.

Now, he appears genuinely convinced that despite the fact that he is widely considered to be a nobody in this race, he has a shot of making the cut when Iowa and New Hampshire voters cast ballots in February.

“When there’s no light at the end of the tunnel, it’s hard to keep things going,” he admits. “And that’s how it’s been for us at the beginning.”

But, he adds, that’s when persistence matters the most.

“I’m going to make a light at the end of the tunnel,” he says. “We’ll just see how big it’s going to be.”

And so, undeterred, he sets off at a brisk pace eastward to Dublin. There’s a lot to do today.

Motivated to serve

When the admiral reconvenes with his team some three miles down the road, the sun has risen and they have a tidbit of good news. Someone called in to C-SPAN to say he’d make a good vice presidential pick for Sen. Elizabeth Warren.

He shakes his head. He’s not doing this to be VP.

“Warren would be a good VP,” he says, with no hint of irony. “She would execute. ... I think she has a talent for that.”

But the president, he says, has to unite the country.

He heads into an auditorium full of restless teenagers at the Dublin School, a private high school, to talk about why he’s the best candidate to do that. Afterward, an administrator comes up and clasps his hand. “I may be the only Republican here, but you could be a great president,” he told the admiral. “I don’t even know what we’re fighting about.”

It’s not an uncommon response from conservatives, who tend to value his public service.

“He’s motivated to serve from deep inside. ... It’s just built into him,” says David Liddy, who as a junior officer willingly worked 100-hour weeks to help Admiral Sestak finish a report on improving the Navy so it could more effectively combat Osama bin Laden and other terrorists. Several days later, the U.S. was blindsided by 9/11.

In New Hampshire, 40% of voters are independents, and can vote in the Democratic primary. Admiral Sestak sees an opening to win them over. But getting media coverage in such a crowded field has been a challenge.  

“The attitude is basically, ‘we have too many people running for president anyhow.’ OK, maybe you do, but maybe the best one is the one you haven’t seen yet,” says Mr. Liddy, who lives in New Hampshire and popped up unexpectedly at one of the day’s events to advocate for the admiral. “I’m really concerned because I’m a Republican, I’ve been conservative my whole life, and I may be shifting parties. ... And here one of the best people I know is running for president, so I’m trying to help.”

“When you don’t get on MSNBC, you go on Cheddar”

By the time Admiral Sestak survives his seven-mile trek from Dublin to Peterborough, walking past a steady stream of Mack trucks, he has recorded seven short video clips for Instagram, ranging from a sunrise stand-up on agricultural policy to one about moon bases.

“One of the biggest hits I’ve gotten was on space,” the admiral explains, referring to an appearance this summer about erecting lunar modules on Cheddar TV, an online channel. “Oh well, when you don’t get on MSNBC, you go on Cheddar. I’ve been on there twice. I also do very well on Breitbart.”

He’s setting up for another video shoot on the outskirts of Peterborough when a police car rolls up, blue lights flashing. It is admittedly an odd scene – a pickup truck pulled off the highway, a man standing directly underneath the green traffic sign for Peterborough and pointing up at it, and a younger man in a suit jacket and hiking boots pulling a knot of wires out of his cargo pants. 

“You folks all set?” the policeman asks quizzically.

“Yeah,” says Evan O’Connell, Admiral Sestak’s communications director, in his perfect British accent.

“You sure?” asks the policeman.

“Yeah, yeah,” they assure him again, and he slowly drives away.

It’s now nearly 1 p.m., and the admiral has a scheduled taping with Politics & Pints, a locally produced video series started by twin brothers Eric and Mike Jackman.

“You’re not Eric or Mike, are you?” asks the admiral as a young man comes out of the brewery.

“No,” says the young man. Then he pauses. “Oh, are you, uh –“

“Joe Sestak,” says the admiral.

By the time he does the interview and pounds a stake into the ground to mark the end of his walk for the day, it’s 2:22 p.m. and no one has had lunch.

The boss doesn’t believe in eating on the road. He says it makes him tired. Yesterday, all he had was a bag of cheddar popcorn – around midnight. Nate Kleinman, an organic farmer who doubles as the campaign’s policy director and driver, has a few sticks of Kate’s butter on the floor of his truck along with a half-eaten baguette, but that hardly counts. Mr. O’Connell is running on fumes from the lobster roll he picked up this morning.

The admiral has a reputation for being a taskmaster – his congressional office was open seven days a week – but he also inspires deep loyalty. Within a week and a half of Mr. O’Connell getting a call from his old boss inviting him to join the campaign, he had quit his job in Paris managing Ernst & Young’s financial services for Europe, Africa, the Middle East and India, and was on a plane to Iowa, temporarily leaving his fiancée behind.

“Of course any sane observer would have to say the odds are stacked against him,” says Mr. O’Connell. But he believes the admiral is the best candidate. Not only does he have a depth and breadth of global experience, he says, but he’s got heart. “Sometimes you have to take a bit of a risk if you really believe in something.”

Late for their next appointment, they wind up lost, wandering around a parking lot. The admiral spots a movie theater advertising “Downton Abbey,” a favorite of his wife and daughter, and stops to take a selfie – by himself. No one recognizes him, let alone asks for an autograph.

Some may shake their heads at his quixotic bid, but those close to the admiral value his conviction that he can make a difference. 

“He knows it’s a long shot but I think he feels it’s important to try, no matter how many people tell him that it’s a long shot,” says his wife, Susan Clark-Sestak, who knows firsthand his dogged determination. On one of their first encounters, a work trip to the Soviet Union, he proposed. She said no. Eight years later, they were married.

“Who knows,” she says, “maybe it’ll catch fire.”

An audience of three

When the admiral walks into the basement of the Peterborough Town Library around 4 p.m., there are six plastic chairs in a semicircle, three of which are empty. The admiral sits down facing two journalists and a local activist whom he won over years ago by writing her a thank-you note after she visited his congressional office.

In a few hours, 12 Democratic candidates will be taking the stage in Ohio for the fourth debate, which will attract 8.3 million viewers.

“I don’t know if you heard, but I’m in the debate,” says the admiral.

The local activist jumps out of her chair and high-fives him. “How’d you get in?” she asks, incredulous.

He clasps her outstretched hand and then explains he’ll be livestreaming his answers to the moderator’s questions later that night. The venue: a Dunkin’ doughnut shop.

About half an hour in, a student at Antioch College who is writing about Admiral Sestak’s climate change plan comes in and starts a second “row.” It’s so quiet you can hear the clock tick. The admiral is there for more than an hour.

They head out to the parking lot and Mr. Kleinman puts what’s left of a broken key into his ignition, and then takes out a wrench to turn it, bringing the truck to life.

As the crew piles in and gets back onto the highway, Mr. O’Connell calls up the team’s operations director, Chris Baker, from the backseat. “Look,” he says, almost inaudibly. “The event just now – small group.”

It’s a short conversation. The admiral wants to talk to Mr. Baker, who planned most of the schedule from the Econo Lodge back in Iowa.

“The day’s been great, thanks so much for what you put together,” the admiral tells Mr. Baker, asking him if he heard that an earlier event at an assisted living center went well. It drew about a dozen residents, one of whom slid her Joe Sestak brochure under the crossword puzzle on her walker.

“I won ’em all!” the admiral says.

He’s not the least bit disheartened about the library event, he says in an interview after getting off the phone.

First of all, he explains, it was mid-afternoon on a workday in a town where most people commute to work. “And the local press was there! So I succeeded where I wanted to succeed,” says the admiral. Plus, he adds, the local activist is very involved on Social Security issues and will “broadcast to her whole network” what she heard.

“So was that a win? Yeah, that was a win.”

It’s a big issue, he concedes, not being able to get on cable TV – though many people have been commenting on the ad he just ran in the middle of “Saturday Night Live.” But like a battle that doesn’t go as planned, it’s just something they have to work around. And he’s been here before. At one early event in his campaign against Senator Specter, only two people showed up: a retired general and his wife.

So if he has to drive for hours to see a handful of people, no problem. 

If he has to walk 105 miles in eight days, including through a Nor’easter, he’ll do it with a smile.

If he has to livestream his “debate performance” from a doughnut shop, where not a single customer pays attention to him, where there are technology glitches and only about eight to 10 people are watching online at any given moment, so be it.

He will keep working 18-20 hour days and gain voters, one at a time.

“Our strategy is a little different because it has to be,” says the admiral. “I have a path that I can see to victory.”