Hillary Clinton, Mitt Romney, John McCain, Al Gore, Bob Dole: All five won their party's presidential nominations after previous failed attempts. All went on to lose.

Democrat Joe Biden hopes to buck the trend as his party's presumptive standard-bearer in 2020 following ill-fated runs in 1988 and 2008. He faces a mercurial incumbent in President Donald Trump, who has never raised his average approval rating above the 40s and now presides over an economy ravaged by the coronavirus pandemic.

Experts tell the Washington Free Beacon that Biden faces historical headwinds as a third-time presidential candidate with more than 40 years in national office. Overcoming decades-old preconceptions and generating voter enthusiasm have been challenges for repeat candidates in the past, and Biden would be the oldest nominee ever at 77.

"Once you've been on the national scene for more than a decade, your odds of winning the presidency are really low," RealClearPolitics elections analyst Sean Trende said. "The second- or third-time runner is part of a broader trend that people who have been in elected office for a long time don't do well, and that's something that has been consistent going back to the 1920s."

Recent elections have shown American voters like fresh faces or familiar incumbents, not also-rans.

Should Trump prevail over Biden, it would mark the eighth consecutive time voters opted for a first-time candidate or incumbent president over his opponent. Repeat candidates have been the losers in five of the last six presidential general elections. The one first-time candidate to lose, John Kerry (D., Mass.), had been in the Senate for nearly two decades when he lost to Republican incumbent George W. Bush in 2004.

The last repeat candidate to win, George H.W. Bush, was the incumbent vice president when he made his second bid for the presidency. Not since Ronald Reagan has someone outside the executive branch made a second run at the White House and won—Reagan beat Bush for the 1980 nomination after an unsuccessful 1976 primary challenge to Gerald Ford.

"Since 1976, post-Watergate, Americans have usually preferred outsiders," University of Virginia professor Larry Sabato told the Free Beacon in an email.

A 2019 PBS report suggested that presenting a new message represents a major advantage in a divided country, which has seen four of the last seven White House winners fail to crack 50 percent of the popular vote. That only happened three times between 1920 and 1988.

"At a time when people are looking for change, maybe it’s harder to be a known quantity," Democratic strategist Mo Elleithee told PBS.

The late senator John McCain (R., Ariz.) captured the 2008 nomination after his failed 2000 run, but his age and reputation as a "maverick" were not assets compared with first-time candidate Obama's "hope and change" message. Hillary Clinton learned a similar lesson in 2016, when she pitted her decades of Washington experience against Trump's outsider message. She used a similar playbook to win the nomination over insurgent socialist senator Bernie Sanders (I., Vt.). That victory came at a cost, as an estimated 12 percent of Sanders's supporters voted for Trump in the general election.

A March ABC News/Washington Post poll found that 15 percent of Sanders supporters prefer Trump to Biden, which could be ruinous for Democrats. Biden has attempted to head off such defections by moving to the left on a number of issues as the primary field whittled down.

Such ideological swings have not fared well in past elections. Romney touted his moderate record as governor of Massachusetts in 2008, but began calling himself "severely conservative" to win the GOP nomination in 2012. The Obama campaign seized on such comments to label Romney a vulture capitalist who lurched too far to the right. The Trump campaign has embraced a similar line of attack against Biden.

"Biden was a terrible candidate the first two times he ran for president and his policies have only gotten worse," Trump campaign deputy press secretary Sarah Matthews said in a statement.

On paper, Biden's campaign has the most in common with Dole's 1996 run. The veteran GOP senator was 73 years old when he captured the nomination after two failed bids. He was widely seen as the Republican frontrunner throughout the year, but entered the primary election weakened after a bruising primary fight with arch-conservative Pat Buchanan.

President Bill Clinton centered his campaign on a strong economy and beat Dole in a rout. His 8.5-point popular vote advantage over the Republican remains the most lopsided margin since Reagan's landslide 1984 win over former vice president Walter Mondale.

Biden exited the vice presidency in 2017 after 44 consecutive years in national office—eight in the Obama administration and 36 as senator from Delaware. His would be the lengthiest such record of any major presidential nominee in history. His résumé far exceeds that of other veteran presidential losers. Clinton had eight years as first lady, eight years in the Senate and four as secretary of state when she ran in 2016; McCain had 25 years in Congress when he ran in 2008; Kerry had 19 years in the Senate when he ran in 2004; Gore had 16 years in Congress and 8 in the vice presidency when he ran in 2000; and Dole had 35 years in Congress when he ran in 1996. That trend does not bode well for Biden, according to Trende of RealClearPolitics.

"We tend to like a low born-on date, and if you think about the [recent] people who have won, Barack Obama, George W. Bush, they're all people who've been governors or senators for less than 12 years," he said. Romney was the exception among repeat candidates, putting in one term as governor of Massachusetts before his presidential runs in 2008 and 2012.

Conversely, the four most recent presidents—Trump, Obama, Bush and Bill Clinton—all won the nomination and then the general election on their first attempts. That quartet had a combined four years of national office experience upon entering the White House, all by Obama as a senator from Illinois. Clinton and Bush—respectively the governors of Arkansas and Texas—had never held national office before entering the White House. Trump had never held office of any kind.

Biden also has the disadvantage of facing an incumbent president. Only five presidents since 1900 have lost reelection; incumbents hold a 15-5 record since then and are 8-3 since World War II. The three successful challengers of incumbents in the modern era—Jimmy Carter in 1976, Reagan in 1980, and Bill Clinton in 1992—had a combined zero years of national office experience. All were current or former governors.

Biden is already different from recent repeat candidates because 2020 marks his first primary success. He had never won a contest until his landslide victory in South Carolina in February, while Clinton, Romney, McCain, Gore, and Dole each won at least five primaries or caucuses in prior runs. Clinton and Romney topped the list, winning 23 and 11 states, respectively, in the 2008 primary.

Biden's 1988 campaign lasted only four months before being derailed by a plagiarism scandal. The then-senator ran again in 2008, but dropped out after winning no delegates in the Iowa caucuses. Now, propelled by a Super Tuesday comeback against Bernie Sanders, he is set to run in the general election on a more liberal platform than either Obama or Hillary Clinton.

MSNBC political correspondent Steve Kornacki likened Biden's comeback in 2020 to Kerry's in 2004—the last time Democrats faced an incumbent Republican. Party leadership was spooked by the surge of another left-wing Vermont candidate that year: then-governor Howard Dean. It wound up rallying around Kerry, who ultimately cruised to the nomination.

"The party base badly wants to beat the incumbent president and prioritized electability," Kornacki said in an email. "At least what it thinks is electability; we'll see if Biden fares better than Kerry in the general election."

George W. Bush defeated Kerry, who is the only Democrat to lose the popular vote since 1988. With the country in the middle of war and still reeling from 9/11, voters stuck with Bush.

With the nation in the midst of a new national crisis in the coronavirus pandemic, Biden has to hope they don't stick with Trump too.