Matthew Dallek, associate professor at George Washington’s Graduate School of Political Management, is author, most recently, of Defenseless Under the Night: The Roosevelt Years and the Origins of Homeland Security.

For the past 3½ decades, a glaring paradox has infected the quest for the American presidency. In an age when citizens on both left and right have soured on politics and treated incumbents with thinly veiled contempt, sitting presidents have rarely been booted out of office before their eight years were up. They have survived, despite the raging animus toward incumbents. The only president since 1984 to have failed to win a second term has been George H.W. Bush in 1992.

Why? One significant reason is that opposition parties have generally nominated bad candidates to challenge presidents running for second terms. Of course, incumbents have built-in advantages, including their claims to a growing economy, their use of the bully pulpit to pulverize their opponents, and their skill at blaming Congress for stymieing the people’s will. But it’s also true that opposition parties have nominated a string of enfeebled candidates who have greased the path to reelection for incumbent presidents. If Democrats want to have a shot at unseating President Donald Trump in 2020, they should avoid making the same mistakes again.


Consider the failed presidential challengers since 1984: Walter Mondale, Bob Dole, John Kerry and Mitt Romney. This list shows that, in the modern era, Republicans and Democrats alike have tended to prioritize decades of government experience or deep party ties ahead of far more salient characteristics and considerations like youthful energy and fresh ideas. Rather than selecting future-oriented/anti-establishment candidates to carry their party’s banner, opposition parties have tended to nominate politicians next in the queue—leaders who have paid their dues by raising gobs of money for other partisans, building chits among activists and elected officials, and incubating relationships with Iowa and New Hampshire political operatives.

This has been a mistake. Maybe these candidates would have made good, or perhaps even great presidents—and we’ll never know whether better nominees could have ousted the incumbents these candidates challenged—but these candidates were weak. They all lacked appeal to an electorate that loathes longtime politicians, and they were brought down at least in part by defects associated with a stale politics rooted in their parties’ respective pasts. (The electorate might dislike longtime pols, but given a choice between two establishment candidates, one incumbent and one challenger, incumbent advantage wins.) They show us how parties can become ossified, reliant on their longtime leaders, and how primary voters and partisan leaders can blind themselves to the demands of the political moment.

In general elections, voters have tended to punish experienced candidates with records of legislative achievement inside the Beltway. Somewhat perversely, the most deserving, qualified nominees have had a harder time winning than their far less qualified competitors. And in those elections since 1984 when incumbency has been out of the question, and two new candidates have run against one another, the forward looking/anti-establishment candidate has won every time with one exception—George H.W. Bush, who in 1988 tore apart Gov. Michael Dukakis as an unpatriotic, soft-on-crime, pro-Big Government Massachusetts liberal. (Although Dukakis was ostensibly the anti-establishment candidate in the race, Bush tarred Dukakis with the brush of 1960s liberalism and pegged him as an establishment throwback to an earlier era.) In 2008, Barack Obama, then a first-term senator, defeated the far more experienced John McCain (in fairness, almost any reasonable Democratic candidate would have prevailed given George W. Bush’s two unpopular wars and the Great Recession), and in 2016 Donald Trump assailed “stupid” politicians and the infinitely more qualified and knowledgeable nominee Hillary Clinton as emblematic of a “corrupt establishment.”

The converse has also held true when, in 1976 and 1980, opposition parties did pick forward-looking/anti-establishment nominees who were able to defeat incumbents. In 1976, Jimmy Carter—his slogan was “a leader, for a change”—vowed to “clean up the mess in Washington” and ousted President Gerald Ford, who had taken office after the resignation of his disgraced predecessor, President Richard M. Nixon, and saved him from possible criminal conviction by pardoning him. Four years later, the shoe was on the other foot. Although he had served as California governor for eight years, Ronald Reagan claimed the outsider mantle by pitching himself to voters as “a boy growing up in several small towns in Illinois” who had “seen America from the stadium press box as a sportscaster, as an actor, officer of my labor union, soldier, office-holder, and as both Democrat and Republican.”

“I am what I always have been, and I intend to remain that way,” Reagan insisted when a reporter asked him whether he was repositioning himself in the political center in anticipation of his White House run.

Ultimately, though, the candidates who failed to unseat incumbents since 1984—the bipartisan Mondale-Dole-Kerry-Romney quartet—underscore this anti-establishment dynamic and hold special relevance heading into the Democratic 2020 primary contest. Romney is arguably the most glaring example of how a weak challenger can hobble the opposition party as it seeks to unseat an incumbent. Although Trump has tweaked Romney for having failed to work hard enough in that campaign (a “choke artist,” he called him), Romney’s far deeper problem was that he became the personification of the age of economic inequality—the greedy, win-at-all-costs corporate raider who grew super-rich on the backs of struggling families. The problem was as much his longtime affiliation with the most elitist elements in the Republican Party as it was with Wall Street. Romney had had only limited government experience, serving four years as Massachusetts governor. Still, as the son of former Michigan governor and GOP presidential candidate George Romney, Mitt Romney had deep party roots. As the country struggled to rebuild after the Great Recession, Romney seemed someone out of central casting from the GOP of yore—a 1930s-era titan of capital who helped define the party as pro-industry, anti-worker and dismissive of middle-class Americans. His nomination made it easier for President Barack Obama to win reelection by opposing what he said was Romney’s elitist, backward-looking economic approach.

In 1996, former Senate Majority leader Dole failed to capture the hearts of the anti-Clinton right, came off as temperamentally cranky, and ran on a noble record of war service in a time when the Cold War had ended and voters prioritized other qualities in their presidents. Above all, Dole was quintessentially a wheeler-dealer, a career legislator and party man to his core who had scant rationale for what his presidency would mean for most Americans. Lambasting Clinton as morally deficient (“Bozo’s on his way out!,” Dole assured one supporter after an October campaign rally in New Jersey), Dole communicated a bitter sense that Clinton’s moral defects had disqualified him for a second term—the antithesis of hope and change.

Reagan would have been tough to defeat in 1984 no matter whom Democrats had nominated. The economy was beginning to expand after a recession and tensions with the Soviet Union had diminished from the height of Reagan’s bombast and the war scares with the Soviet Union in 1983. Still, Mondale was easily caricatured as an unapologetic liberal with a static vision born of 1960s-Big Government activism that voters had at least in part rejected in Reagan’s 1980 victory. Having served as Carter’s vice president and as a senator from Minnesota, Mondale ran on what he described as his government “experience” and his record as “the most active and influential vice president in history.” On Election Day, he carried only his home state and Washington, D.C., in the Electoral College.

Perhaps the strongest of the four challengers in question was Kerry, and he prosecuted with ardor the argument that Bush’s occupation of Iraq had failed. Yet his political experience and legislative record also became an albatross for him. He had served as a senator for decades, had voted for war in Iraq, and Republicans used his antiwar Vietnam activism and his patrician mien and background—a “wise man” knowledgeable in foreign affairs and a symbol of his party’s establishment—to depict Kerry as vaguely anti-American. His career and social class played into Bush’s structural advantage in the election as the incumbent commander in chief during wartime and made it easier for the Bush campaign to cast Kerry as unprincipled and a candidate of yesterday.

What does this recent history reveal about the Democratic Party’s prospects going into 2020? Trump plans to run for reelection by attacking “certain Democrats” and “politicians” who refuse to aid “women and girls … tied up in the back seat of a car or a truck or a van” in what he falsely labeled an immigrant-fueled crime wave, as he argued in his Friday remarks from the Rose Garden declaring a national emergency. Running against Washington may not be as easy for Trump as he wishes it to be. His norm-shattering presidency has squandered one of the advantages incumbents traditionally have enjoyed, as he has failed in his first term to convince a majority of the public that the president is actually presidential. So it is thus conceivable that a nominee with deep experience—think former Vice President Joe Biden—might well be a safe harbor in a Trump-induced Category 5 storm. It’s not crazy to envision at least some significant slice of the electorate seeking a candidate with policy knowledge, Washington experience and a stable character, bucking the trends of the past four decades.

At the same time, the opposition party’s ignominious record since 1984 should factor into any assessment of what is shaping up to be the deepest, most diverse crop of Democratic presidential candidates ever. The quartet of failed challengers reminds us that an electorate deeply hostile to Washington politicians will likely look askance at any Democrat whose legislative and political achievements define their quest for the American presidency. Democrats will need someone skilled at tapping people’s frustration with politics, someone credible on the central question of income inequality, someone who can speak to the party’s future rather than someone beholden to its past. Sadly, nominating the most qualified person to be president may squander a chance—perhaps the biggest since 1992—to oust an incumbent president.