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Magazine | Neil Swidey

The Democrats’ choice problem: Which candidate can beat Trump in 2020?

Fifteen hopefuls (so far) are vying for the chance to face President Trump in 2020. If the field remains big for too long, though, it could benefit the same candidate who shook up the system in 2016.

images from adobe stock; globe staff illustration.

THERE WAS A STRAIN OF WISTFULNESS woven through the obituaries for Mario Cuomo after he died on the first day of 2015. The tributes for the New York governor and stirring orator who was the dream presidential candidate for many Democrats in 1988 and 1992 were weighed down by a sense of what could have been, if only he had run. In the waning days of 1991, the indecisive governor nicknamed “Hamlet on the Hudson” went so far as to keep a plane idling at the Albany airport, ready to deposit him in New Hampshire before the filing deadline for the first-in-the-nation primary.

Cuomo probably did himself a favor by staying out of the presidential hunt. Democratic voters are notorious for their buyer’s remorse, practically begging charismatic politicians to jump into the race, only to sour on them quickly and go back to longing for some idealized replacement on the sidelines. Well before there was Tinder, Democrats have seemed unable to stop swiping left.


Yet the 2020 Democratic presidential campaign is shaping up very differently. Already, the sidelines are barren as pretty much all of the party’s most promising players have crowded onto the field of candidates. The most notable exception is Joe Biden (who may well have decided to get into the game by the time this article is published). If Biden does run, it’s doubtful he will saunter to the top of the depth chart the way his favorability ratings and supporters suggest he will. That’s not just because he would be 78 by the time of the next inauguration. Remember that this would be his third run for president, and, let’s face it, the first two were fairly disastrous.

Over the years, the Republican Party has usually functioned as predictably as a Rotary Club, advancing the runner-up from the previous campaign into the top slot as a reward for time served (as with Ronald Reagan, George H.W. Bush, Bob Dole, John McCain, and Mitt Romney).


Democrats, meanwhile, toss their standard-bearers and runners-up to the curb more joyfully than Marie Kondo throws out old slacks. Hillary Clinton in 2016 was the exception to this pattern — a departure that, given the result, is unlikely to be repeated, at least if Democrats want to win. Who was the last non-incumbent Democrat to win the Oval Office after having previously run for president? Try James Buchanan, in 1856, which was half a century before the White House actually had an Oval Office.

This time around, Democratic voters should have no reason to look longingly at the sidelines. Already 15 Democrats have formally announced or are actively running with exploratory committees, and another half-dozen hopefuls might still jump in. While there’s no obvious front-runner yet, that’s only because any number of the candidates could conceivably rise to the top.

With the party’s first national debates less than three months away, and the New Hampshire primary less than 11 months away, the big challenge for Democratic voters will be how to make sense of what could well be the largest field in history — and eventually pare it down into something more manageable. For candidates, the task will be even harder: how to stand out in such a crowded pack, without doing anything so bold it could backfire.


So far, 15 Democrats have entered the race for president. Former vice president Joe Biden is still considering his options. Globe Staff Photo Illustration

A big field without an obvious front-runner could shake out in any number of ways, but history suggests it will most likely end up following one of two paths.

The first is the long, (mostly) collegial search for a consensus candidate. That’s what we saw with the relatively large Democratic field in 1988 (11 candidates, plus a few fringe). In that race, the big names either sat out or flamed out early, and the campaign turned into a slow-moving grind where the combat was generally mild and Michael Dukakis eventually emerged as the compromise nominee. The 2004 campaign started out in similar fashion, though the consensus candidate — fellow Massachusetts pol John Kerry — took the reins sooner.

The model for the second possible path is a lot more recent: the Republicans in the 2016 campaign. That cycle saw an unwieldy 17 hopefuls vying for the nomination, with more of them remaining in the race for longer than usual. It led to the preposterous first “junior varsity” debate where the seven lowest-polling candidates squawked at one another at the kids’ table before a tiny pre-dinner audience of precinct captains and lonely hearts. Even the “varsity” debate, held in prime time that same night in the cavernous home of the Cleveland Cavaliers, had to cram 10 candidates onto the stage, with Ohio’s popular two-term governor positioned so far to the side that he was almost backstage, and not allowed to speak until more than 20 minutes in.


All of this primary congestion played into the hands of exactly one candidate: Donald Trump, who used his mastery of reality television to command attention. He dispensed with the usual formalities in favor of a let’s-cut-the-crap attitude, replaced policy talk with unflattering yet catchy nicknames, and devoured most of the limited bandwidth that Republican voters had for the gestating campaign.

In the current media climate, and with a Democratic 2020 field that promises to be just as cumbersome, will the candidates be able to avoid turning this into another reality sideshow? The contenders insist the answer is yes, suggesting they will focus on substantive policy discussion and respectful debate. Cory Booker has characterized his fellow US senators who are now presidential competitors as his siblings. “They are friends, they are sisters,” he said on The View. “There will be some sibling rivalry. But at the end of the day we’re family.” Some prominent Democrats are calling on all the candidates to pledge not to attack one another during the primaries, for fear of sowing division that Trump would surely exploit in the general election.

In the heat of the campaign, though, when trailing candidates get desperate, will this family be able to avoid drag-down feuds? And would such restraint even be in the best long-term interests of the Democrats?

After all, what an effective primary campaign does is put the candidates through a punishing stress test that toughens and strengthens them, giving everyone confidence that they have identified the strongest possible contender for the general election. That happened with Barack Obama in 2008 and Bill Clinton in 1992, but not with Hillary Clinton in 2016. Her campaign’s steamroller approach to clearing the field and turning the primaries into a coronation rather than a nomination backfired by helping to propel the insurgency of Bernie Sanders.


And it didn’t happen with the Democratic nominees in 1988 or 2004, as both Dukakis and Kerry seemed unprepared for the take-no-prisoners attacks they faced from their Republican opponents. Dukakis viewed the Willie Horton furlough attack ads launched against him in the ’88 general campaign as being so distorted they weren’t worthy of a response. Kerry held his fire in ’04 when the Swift boat attack ads cast aspersions on his valor in Vietnam. In both cases, the attacks may have been cynical and unfair, but they turned out to be devastating. Democratic voters would have been better off if the nominees had been more ferociously tested during the primaries.

Even if Mario Cuomo had been the nominee, he would probably have been just as flat-footed. Dukakis tells me that, early on in the fall of 1988, Cuomo advised him: “Keep it positive. Don’t worry about this Willie Horton thing.” Four days before the November election, during a campaign swing through Queens, Cuomo pulled him aside and apologized, telling Dukakis, “That was the worst advice I ever gave.”

The biggest risk to the Democrats isn’t that the candidates will be too mean to one another in the primaries as the field winnows — it’s that the field won’t winnow.

Mario Cuomo was the dream presidential candidate for many Democrats in 1988 and 1992.Associated Press/File

THE FIRST TIME I MET Michael Dukakis was in Filene’s Basement. It was the 1970s, when he was deep into his first term as governor and I was deep into elementary school. I was on school vacation and in line with my dad when we noticed Dukakis standing behind us, holding a trench coat. My dad struck up a conversation with him. “Kitty got me this,” Dukakis told us, pointing to the tan coat draped over his arm, “but the sleeves don’t fit right.”

Here he was, the sitting governor, and instead of dispatching an aide to handle this chore, he used his lunch break to walk by himself from the State House to Downtown Crossing and wait in line. Just like the rest of us bargain hunters.

Voters often tell pollsters that what they want most in their politicians is authenticity. They’re sick and tired of cagey or overly careful candidates who don’t say anything that hasn’t already been vetted by multiple focus groups. They want someone who will level with them — straight up, no chaser. President Trump benefited from this impulse, a billionaire who very effectively used his fondness for unfiltered, often intemperate comments (and Kentucky Fried Chicken) to present himself as a man of the people.

Still, voters may not prize authenticity as much as they like to believe. After all, by a wide margin, they passed on Dukakis. Criticize his politics if you like, but Dukakis has to be one of the most authentic and decent people in the history of modern public life. Here’s an 85-year-old guy who picks up litter on his walk to work and lets strangers drop off turkey carcasses at his house after Thanksgiving. He’s funny and easy to talk to, and he seems entirely incapable of artifice.

During a recent call with him, when the conversation goes much longer than expected, I hear his wife complaining in the background. He makes no effort to hide Kitty’s pique, chuckling as he tells me, with obvious affection for her, “I think I gotta run. My bride is starting to get annoyed.” (I hear her in the background correcting him: “Very annoyed!”)

Yet somehow lots of voters around the country in 1988 saw him as wooden and almost robotic. Some blame for that rests with the media’s penchant for caricature and political handlers’ addiction to stage managing, since this problem is hardly specific to Dukakis. The two other presidential nominees I have gotten to know, John Kerry and Mitt Romney, are much funnier and more natural behind the scenes than their public images would suggest.

But a big part of the problem no doubt springs from the fear that candidates understandably have of getting caught saying something that could unwittingly sink them.

Nearly a decade ago, I attended a talk Dukakis gave at Tufts University. Challenging the students in the audience to get into public life — but to avoid the pitfalls that have claimed other political careers — he advised them to “get off their cans” and “have a good but conventional sex life.” MSNBC’s Chris Matthews, who moderated the talk, let out one of his signature muscular “ha!”s and marveled, “ ‘Get off your can’ and ‘have a good but conventional sex life’ — if you had talked like this in ’88, you would have been president!”

That may be true. Or one of his unscripted comments could have killed his campaign. (That’s exactly what happened to Romney’s father, a lesson that young Mitt probably learned too well.) The risk seems especially acute in the current political climate, with social media an ever-present outrage amplifier.

Will 2020 shake out like earlier big Democratic fields in 1988 and 2004? Here, 1988 nominee Michael Dukakis appears at the 2004 convention.Paul J. Richards/AFP/Getty Images/AFP/Getty Images

Trump, of course, said hundreds of outrageous things during the 2016 campaign, any one of which would have been automatically disqualifying for any other candidate in any other race. But there’s no getting around the fact that he was held to a different standard. I remember telling someone during that campaign why all the dutiful fact checking of Trump’s statements by various media outlets wouldn’t matter. He wasn’t being judged as politician but rather as a celebrity, like Kim Kardashian. Overhearing this, my middle-school-age daughter objected, saying, “That’s not fair to Kim Kardashian. She is very honest with her fans.”

So this is the tightrope that Democratic contenders will have to walk: They’ll need to be unfiltered and distinctive enough to break out of the pack, but not so candid that they get disqualified by the wrath of summary judgment on social media.

“I’m the last guy in the world to consult on campaign strategy,” Dukakis tells me, “given what happened in ’88.”

But he advises a specific line of attack against Trump. “He’s a nickname guy, and we know he’s a congenital liar. I’d start calling him Pinocchio, and stick with it. Get some cartoonist to draw him with lederhosen and a cap.” Every time Trump utters something false, repeat the refrain: “Oh, the nose is growing again.”

Who knows? It could work. More likely, though, Trump would find a way to turn it around. Tutored by Roy Cohn, raised in the just-spell-my-name-right combat of New York tabloids, and judged by the rules of celebrity exceptionalism, Trump is simply a pro at these kinds of street fights.

Witness Elizabeth Warren’s elaborate rollout last fall of her Native American DNA test results. The slickly produced video, the talking points, the demand that Trump make good on his pledge to pay $1 million to charity if a DNA test proved she had Native American ancestry — all of this was obviously designed to put the president on the defensive. Yet it took him no time to turn it back on the senator, dismissing her claim to distant heritage as “one 1,000th” and then tweeting out a doctored form of her campaign logo to read “1/2020th.”

Two New England lawmakers — Bernie Sanders and Elizabeth Warren — are seeking the Democratic nomination in 2020. Barry Chin/Globe staff/File 2017/Globe Staff

IN EVERY PRIMARY RACE, there comes a time when a candidate has to catch fire through differentiation — or recede into the background.

In the 1976 race, a record 16 candidates in the Democratic primaries jostled for the chance to run against a Republican incumbent wounded by Watergate fallout, until Jimmy Carter surprised everyone but himself. That campaign — with its urgent need to thin the herd — popularized the phrase “winnow out” in presidential politics. (After he edged out several better-known candidates to come in third in the Iowa caucuses, former Oklahoma senator Fred Harris boasted that he had been “winnowed in.” A month and a half later, Massachusetts voters winnowed him out.)

In 1988, after the early shipwreck of Gary Hart, the klatch of remaining Democratic contenders battled in mostly benign fashion until Dukakis took command. How benign? When Joe Biden had to drop out after he was shown to have plagiarized a speech almost word for word, a story that Dukakis campaign manager John Sasso had tipped off the media to, Dukakis fired Sasso. (Other candidates would have given him a raise.)

In 2004, Kerry managed to avoid most of the intramural Democratic bickering, watching as Howard Dean (after his aborted front-runner phase) and Dick Gephardt engaged in hand-to-hand combat that became so inflamed it looked like a murder-suicide pact.

John Lapp, a longtime Democratic strategist and key Gephardt adviser during that race, says the knock-down fight with Dean in ’04 was a reflection of the intense pressure on candidates to break away from the pack. “You cannot douse yourself in gasoline and call that catching fire,” he says.

As for 2020, despite the Democratic vows to be collegial, Lapp expects that combat will grow more intense as all these candidates who line up so closely on policy feel increasing pressure to stand out.

Overall, though, he is upbeat about the depth and quality of this Democratic candidate roster. Some contenders who will be seen as second-tier would have been automatic starters in a less competitive cycle, he says. “It’s like when Charles Barkley came off the bench for the Olympic Dream Team.”

At some point, the race will break. In 2008, that happened when Barack Obama won Iowa, disproving conventional wisdom that an African-American candidate wouldn’t be able to win such a white, rural state, and rendering worthless all the endorsements Hillary Clinton had racked up from prominent African-American leaders. Then it became a real contest between two viable candidates, with the stronger one ultimately prevailing.

“That’s what primaries are supposed to do,” says Susan Estrich, the Democratic strategist who took over the Dukakis campaign in 1988. “You take Barack Obama, a one-term senator, and by the time he wins the nomination from Hillary Clinton, he’s a hell of a lot bigger than when he started.”

The 2008 pattern could be repeated in 2020, with the strongest pair of contenders emerging after New Hampshire or South Carolina, and the others eventually singing the song of the also-ran by holding the obligatory news conference and reluctantly admitting they no longer see a viable path to victory.

But that assumes the pressures that have historically forced also-rans to accept reality are still strong, when in fact they’ve never been weaker. Gone are the days when powerful party bosses called the shots (even the super-delegates have been neutered), when a small group of gatekeepers in the mainstream media could effectively disqualify a candidate they considered unserious (as they did in 1992 when Pat Buchanan ran on issues Trump would take up a quarter-century later), and when the big campaign cash largely came from a central spigot (as opposed to today’s diffuse financing landscape, where the check-writing super-rich are spread out like sprinkler heads on a golf course). If none of those forces holds anything close to the sway they once did, what’s to stop a bunch of candidates from lingering in the race, if only as an extended tryout for a talking head gig on MSNBC?

Meanwhile, as Trump proved, the longer the field remains crowded, the more likely it is that you can win without expanding your base and working to build a majority coalition.

During the 2016 Republican race, Donald Trump (here with Senator Ted Cruz) used the crowded field to his advantage, especially in the debates. Chip Somodevilla/Getty Images/Getty Images

AT THE FIRST REPUBLICAN DEBATE in Cleveland in August 2015, as all the candidates tripped over each other in their effort to stand out, Donald Trump seemed to do it without even trying. When the Fox News panel started with the obligatory question asking each candidate to raise his hand only if he would not commit to supporting the eventual Republican nominee, Trump was the only one whose arm went up.

While the other contenders betrayed their eagerness to uncork the lines they had clearly been honing during extensive debate prep sessions, Trump appeared as relaxed as a former fullback offering his insights on the NFL pregame show. Rather than deferentially waiting for the moderators to finish their questions, Trump cut them off mid-sentence, but in a conversational, rather than confrontational, way.

As the debate wore on, his performance reminded me of the way contestants on the CBS reality show Big Brother sit in the “diary room,” talking directly to the camera while offering takedowns of their fellow houseguests behind their backs. Except Trump was doing it right in front of them. “You’re having a hard time tonight,” he told Rand Paul with a smirk, after the Kentucky senator tried going after Trump. That was enough to quiet Paul.

In subsequent debates, of course, he would roll out his cutting nicknames — “Low-energy Jeb” (Bush) and “Little Marco” (Rubio) and “Lyin’ Ted” (Cruz). That’s standard fare for reality TV, but the nicknames stuck because they surgically encapsulated a weakness that others in the party had seen in that particular candidate.

Given the size of the field in the early debates, there was no hope the events would be edifying. Trump ensured they would at least be entertaining. And as much as people in the media complained about his tactics, he was giving them something they desperately wanted: ratings for the broadcast and cable channels, and clicks for the rest of the media. (Meanwhile, by insisting that the Democratic primary debates be held on low-ratings Saturday nights, risk-averse Hillary Clinton was ceding all this free media to Trump.)

Why did the other Republican contenders, especially people like John Kasich and Chris Christie, who were old hands at the cable TV sound-bite game, sit back and let Trump steal the show?

In recent interviews plugging his new book, Christie has admitted that he and the other “serious” candidates misread the situation. Assuming that Trump was running just to enhance his brand (probably true), they figured that, instead of taking him on, they’d simply wait for him to fizzle out (a spectacular miscalculation).

Few people know more about the Republican New Hampshire primary than Tom Rath, a former state attorney general. But even he was shocked by how events unfolded there in 2016. As a key adviser to Kasich, he worked hard to prepare his candidate for the debates. “You can’t believe how frustrating it is,” Rath says, “when you realize that nothing you’re doing is amounting to anything.”

Based on candidate poll numbers going into debates, Trump was placed center stage and went on to dominate most of the evenings, which only reinforced his poll numbers.

Still, because there were so many candidates, Trump won New Hampshire with just 35 percent of the vote. “That should be a warning to the Democrats and their crowded field,” Rath says. “Their front-runner could very well come out of New Hampshire validated by a primary where two-thirds of the voters voted against that person.”

More important: Trump remained a minority front-runner for most of the primaries. He didn’t get 50 percent or more of the vote in any state until his native New York, the 36th state contest on that year’s calendar. In contrast, it took Dukakis just six contests to clear the 50 percent threshold; Bill Clinton, Kerry, and Romney, five; and Obama and George W. Bush, four.

When candidates are working to get over 50 percent, they have to do the kind of coalition-building that will give voters a good preview of their governing philosophy. But if a candidate is simply trying to protect an existing base of 30 percent or so, that will work very different muscles and incentivize very different decisions and, more than likely, produce a very different kind of nominee. As it turned out, Trump did give voters an accurate preview of his governing philosophy since, as president, he has shown himself to be much more committed to feeding his base than to growing it.

Senator Kamala Harris of California campaigns in Mancheser, New Hampshire, in February. Craig F. Walker/Globe staff/Globe Staff

IT’S A FRIGID, SNOWY Presidents’ Day in New Hampshire, and I’m standing in the back of historic South Church in Portsmouth as Bruce and Nancy MacDougall squeeze in next to me, behind a row of TV cameras. They waited in the cold for more than an hour for the chance to see Senator Kamala Harris speak. Inside, the spacious church is packed with about 1,000 souls, and several hundred people behind them in line are being turned away at the door.

Suddenly, a bald, bearded man in a plaid shirt appears, telling the MacDougalls they can’t be in the press area and will have to go. When they protest, he cuts them off. “You have to leave! The fire department is not going to let her go on until the back row has been cleared.”

The MacDougalls are upset but eventually agree to exit. Then the bald, bearded man in plaid heads toward the pulpit and grabs the microphone. It turns out he’s not the church’s security guard, but the chair of its board of directors as well as the opening act for today’s event.

“We celebrate the dignity of all people,” he tells the crowd. “If you’re from some South American or Middle Eastern country and you have traveled across the border to be with us today, you’re welcome here!” The crowd applauds and whoops. “If you are straight, gay, bi, trans, queer, or questioning, you’re welcome here. If you’re Christian, Jewish, Muslim, an atheist, a humanist, or a Buddhist, you’re welcome here.”

I can’t help imagining the MacDougalls shivering outside, asking “What about us?” as he proclaims the Democrats’ big tent approach.

When Harris appears, the crowd bathes her in applause. The California senator handles herself well, coming across in her talk and the lengthy Q&A period as both confident and casual.

It might be tempting for the Harris campaign to interpret this enthusiastic and unusually large turnout by New Hampshire voters so early in the season as evidence that she is the clear front-runner. But that would be a mistake. After all, Cory Booker had drawn several standing-room-only crowds elsewhere in New Hampshire during the previous two days, and Senator Amy Klobuchar would attract a big turnout later that same night an hour west of here.

At this point, antipathy for Donald Trump seems to be animating the big, eager New Hampshire crowds more than any of the candidates themselves.

Before they were shown the door, the MacDougalls told me they hadn’t shown up to cheer Harris so much as to size her up: Does she have what it takes to beat Trump in the general?

Bruce is an independent and his wife is an independent turned Democrat, but they stress that this election will be about only one thing: “Job number one is to defeat Trump,” he says.

Yet if the Democratic field remains crowded for longer than usual, the calculus for winning the primaries could be a world apart from the one for winning the general. Conceivably, a candidate could “win” simply by hanging on to an unshakable base of 30 percent  for most of the campaign — until eventually getting over the 50 percent hump to avoid a brokered convention. There are always predictions of deadlocked conventions, though they never come to pass anymore. But because of the Democrats’ primary calendar and how they award delegates on a proportional (rather than winner-take-all) basis, 2020 could be the year.

US Senator Corey Booker announces his run for US president on February 1 outside his home in Newark, New Jersey. Dominick Reuter/AFP/Getty Images/AFP/Getty Images

The Democratic National Committee appears determined to avoid the sand traps from the 2016 Republican debates. Instead of using poll numbers to divide the candidates between varsity and JV debates, the Democrats will split up the candidates randomly, airing pairs of debates on back-to-back weeknights. To qualify for a spot on the stage, candidates will either need to register at least 1 percent in three specific national polls or meet certain thresholds for donations.

These measures should ensure more fairness in the process. But they won’t ensure the debates will be edifying or entertaining.

Through his actions in the crowded 2016 race, Trump changed the game for Republican presidential politics. The question is whether his new rules will seep into the crowded Democratic debates this time.

After a few earnest Ambien events, will some campaign manager begin pressing a stuck-in-neutral Democrat to try to get ahead, Trump-style? If Trump were on the stage, it’s not hard to think of the nicknames he’d invent to highlight a Democratic hopeful’s perceived weakness.

Booker’s coziness with Wall Street and Silicon Valley? “Corporate Cory.”

Kirsten Gillibrand’s once 100-percent positive rating from the National Rifle Association? “Kirsten Get Your Gun.”

Joe Biden’s age and previous campaign failures? “Play It Again Joe.”

Beto O’Rourke’s preference for generalities over specifics? “Zero O’Rourke.”

After a raft of stories about her alleged mistreatment of her staff, Klobuchar is probably most vulnerable to a cutting nickname: “Bad Boss Amy.”

The volume of chatter and negative stories Klobuchar has been hit with could suggest other camps view the Midwestern moderate as a threat they’d like to see neutralized early. But if she manages to survive this onslaught, she will emerge stronger. Already she has picked up support from fans of the Julia Louis-Dreyfus masterpiece Veep, since one of the lines Klobuchar is said to have unleashed on her staff, when she was at an event and parched, could have been part of an Emmy-winning script: “I would trade three of you for a bottle of water.”

I’m not recommending that the Democrats resort to mockery. It’s a dangerous game unless you’re a pro at it, like our current president. But there is some precedent for it. Remember mild-mannered Walter Mondale in 1984 with his “Where’s the Beef?” meme, designed to stop a surging Gary Hart?

Many Democrats can imagine nothing worse than a primary that devolves into name-calling. But here’s a scenario that would be much worse for them: If the nicknames don’t come out until the general election.

Neil Swidey is the Globe Magazine’s staff writer. E-mail him at swidey@globe.com. Follow him on Twitter @neilswidey. Get the best of the magazine’s award-winning stories and features right in your e-mail inbox every Sunday. Sign up here.