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Can Trump Win Again In 2020?—And How

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Saagar Enjeti White House Correspondent
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The news the day before the 2016 presidential election did not look good for Donald Trump.

His “anxious” candidacy was merely a “last stand” against then-candidate Hillary Clinton, the New York Times stated flatly. Polling website FiveThirtyEight put Clinton’s chances of winning the election at 71%. That was much too pessimistic for those at the Huffington Post, who slammed FiveThirtyEight editor-in-chief Nate Silver. Actually, they huffed, Clinton’s chances were more like 99%.

The giddiness among Washington’s political class was best shown by the Huffington Post headline, preparing in earnest for the end of a nightmarish election and a return to establishment normalcy. The Clinton campaign basked in the coverage, and all her senior aides assured her on the day of the election that not only would she win, but that she would win in a landslide.

All except one.

Senior Clinton adviser Jake Sullivan warned his comrades repeatedly that Clinton would likely lose and begged the campaign to put her in states across the Midwest. It was a sentiment Hillary’s husband Bill expressed early on, to which junior aides told him “with a wave of the hand” to be quiet, Politico reported.

Clinton instead was sure of her victory and spent time in deep red states like Texas and Arizona, just one week before election day.

In the most extraordinary presidential victory since Truman trounced Dewey in 1948, the mood across the Acela corridor shifted tectonically as the clock struck 11 p.m. and the nation began to realize that former reality TV star Donald Trump was about to occupy the same office as George Washington.

Now we’re on the eve of the Democratic nomination cycle and more than a dozen candidates are seeking to replace Trump, each encouraging the other to trend further leftward. A Democratic party official speaking on the condition of anonymity told The Daily Caller that worries of repeating the GOP’s mistake in 2016 abound within the party.

The official said several party aides are worried that splits between candidates on Medicare for All, the Green New Deal, the Supreme Court and whether to prosecute Trump will cripple the eventual nominee, who will enter the 2020 general election weakened by a tough primary.

“It’s a reasonable possibility,” Democratic strategist Simon Rosenberg told the Caller, acknowledging that “there’s no question that it’s a possible scenario” that the Democratic primary will make the eventual nominee easier to attack.

“By the fall, this will be a tough, hard–hitting primary,” he said previously.

How Did He Do It? 

Trump was swept into office with 306 electoral votes to the 232 received by Hillary Clinton, though he lost the popular vote by a margin of 2 million votes: 63 million to Clinton’s 65 million.

Trump was barely getting used to the title of president-elect before the political class began discussing whether he could pull off his impressive gambit yet again in 2020. Analysts were quick to point out that Trump’s margin of victory in the three key states of Pennsylvania, Michigan and Wisconsin were immediately held up as evidence of his vulnerability in a future race.

“Michigan, Wisconsin and Pennsylvania account for 46 electoral votes. If Clinton had won these states, she could have sealed the presidency with 274 total electoral votes,” the Washington Post noted days after the election, adding, “This election was effectively decided by 107,000 people in these three states. Trump won the popular vote there by that combined amount. That amounts to 0.09 percent of all votes cast in this election.”

Michigan, Wisconsin and Pennsylvania represent several midwestern states that swung solidly toward Trump in the 2016 election despite repeated support for former President Barack Obama, including Ohio and Iowa. Trump also flipped the state of Florida delivering him the presidency.

Trump’s victory lies not just with the 100,000 voters across Michigan, Pennsylvania and Wisconsin who voted for him, but also with millions of working-class white voters who came out in record numbers to back him.

News analyses the day after the election were replete with stories of counties which Obama had won by double digits enthusiastically supporting Trump. The New York Times summarized their post-election analysis, saying, “The truth was that Democrats were far more dependent on white working-class voters than many believed.”

Can Trump Win Again? 

The razor-thin margin of Trump’s victory was not lost on him and his advisers during his two years in office.

Trump’s first term had many policy priorities, from an obsession over how to boost the U.S. economy and reform the U.S. healthcare system to building a wall along the southern border. Above all, the White House focused on attempting to renegotiate trade deals.

Trump’s agenda has hit roadblocks, with limited success fully repealing and replacing the Obamacare framework or any meaningful immigration reform. The economy under Trump, however, is undoubtedly roaring with a record low 3.9% unemployment rate, rising wages and a roaring stock market.

Trump has also seen success in protracted trade negotiations with China after levying heavy tariffs, re-negotiating a new trade agreement between Canada and Mexico and scoring a new trade agreement with South Korea. Trump is also reducing the U.S. troop levels in Syria and Afghanistan and has held a protracted standoff with Democrats over funding for his border wall.

Interspersed throughout Trump’s policy victories have been a litany of staff departures, controversial tweets, endless fights with the mainstream media and cultural flashpoints on gun control, white nationalism and the kneeling policy of the NFL.

Trump’s masterful playing of the U.S. media and the generally good state of things nationally put him in a position where multiple analysts and observers say that he very well could, once again, convince voters to take a chance on him.

These analysts and observers told the Caller the strong growth of the U.S. economy seen under the Trump administration, the absence of an unpopular foreign war and the mid-range popularity numbers, hovering in the 40th percentile nationally, all are good signs for the president heading into the 2020 general election.

US President Donald Trump addresses a "Make America Great Again" rally at Bozeman Yellowstone International Airport, November 3, 2018 in Belgrade, Montana. - With rallies in Montana and Florida, a state he had already visited on Wednesday, Trump on Saturday is keeping up his relentless campaign schedule before Tuesday's ballot, which has become a referendum on his unconventional presidency. (Photo by Nicholas Kamm / AFP) (Photo credit should read NICHOLAS KAMM/AFP/Getty Images)

US President Donald Trump addresses a “Make America Great Again” rally at Bozeman Yellowstone International Airport, (Photo by Nicholas Kamm / AFP/Getty Images)

“Trump is reasonably close to 270 at the present time, and he carried WI and PA in 2016. Mathematically, a Trump victory is well within reach,” Director of the UVA Center of Politics Larry Sabato told the Caller in an email.

Sabato pointed to his analysis that Trump could once again win re-election by emphasizing the same issues he did in the 2016 presidential election.

“The president’s base-first strategy could again deliver him the White House, thanks in large part to his strength in the nation’s one remaining true swing region, the Midwest,” he explained.

Sabato warned, however, that “arguably, the state of the economy is the most important factor: If perceptions of its strength remain decent, the president could win another term. If there is a recession, his odds likely drop precipitously.”

Two sources familiar with Trump’s 2020 general election strategy tell the Caller that Trump plans on doing exactly what Sabato suggested. These sources say Trump will barnstorm every swing state and sing his own praises, pointing to his accomplishments in office.

Dr. Victor Davis Hanson, a respected historian and author of “The Case For Trump“, said he firmly believes Trump has a path to victory in 2020.

“The key is to hold the middle and working classes who came out in 2016 to flip the purple swing states. He can do this by trumpeting the data of his economic successes (from unprecedented rises in workers’ wages to near-record peacetime low unemployment), and sharpening the cultural contrasts with his ever more radical opponents,” Hanson wrote to the Caller over email.

Hanson assessed Trump as a singular historical force, likening him to “sort of like the famous 2004 Apple Macintosh commercial, in which the young female athlete throws runs into the 1984ish crowd and throws her hammer into Big Brother’s screen smashing the orthodox Big Brother voice.”

Scott Adams, creator of Dilbert and early predictor of Trump’s victory ahead of the 2016 presidential election, predicted to the Caller that Trump would win again in 2020. Adams noted his belief that the main impediment to those who would not vote for Trump in 2016 has been removed and that Trump’s base-first strategy was useful. “We no longer live in a world where you can persuade the other team,” Adams said, adding that the winner now will be “whoever best persuades their own team.”

Their analysis is reflected in Trump’s 2020 campaign slogan “Keep America Great,” which is an extension of his 2016 refrain “Make America Great Again.” (RELATED: Trump Reveals Slogan For 2020) 

The campaign, meanwhile, is assembling a campaign war chest like no other, with $19 million in its bank account. A CNN profile of the campaign notes that the Trump campaign and the Republican National Committee have “merged their field operations and fundraising efforts and will share office space,” enabling the RNC to bear significant costs.

What Role Do The Democrats Play?

(Photo by Ethan Miller/Getty Images)

U.S. Sen. Bernie Sanders (I-VT) speaks during a rally for Nevada Democratic candidates at the Las Vegas Academy of the Arts on October 25, 2018 in Las Vegas, Nevada. (Photo by Ethan Miller/Getty Images)

Sabato, Hanson and Adams all noted that 2020 may have less to do with Trump than with his eventual opponent. Fifteen Democrats are currently running for president, with former Vice President Joe Biden is also expected to also announce in coming weeks that he will join the race.

FiveThirtyEight editor-in-chief Nate Silver noted recently that “the high number of candidates does imply a higher-than-usual risk of chaos,” noting that “in primaries since 1972 that haven’t featured an incumbent president, parties have averaged about 10 major candidates for president. So Democrats are looking at roughly double the average.”

Silver warns that “past electoral cycles where the field was nearly as big as this one shouldn’t exactly be comforting to Democrats” and that “Democratic voters like a lot of their choices and feel optimistic about their chances of beating Trump in 2020. The large field is both a sign that there may not be consensus about the best candidate and a source of unpredictability.”

Rosenberg acknowledged that there is a possibility that the large field could be crippling but pointed to the primacy of Biden in polls among the primary base. “Almost every primary, the pragmatist won. This idea that the Democratic party is purely ideological […] it didn’t happen in 2018,” he rebutted, adding that, in his view, “the party is actually far more together than its been in a long time.”

A Democratic official, however, said that others were especially worried that Trump would gleefully trumpet progressive statements made by candidates during the primary, especially on matters relating to immigration, the environment and healthcare. Trump will point to any Democratic proposal for large government intervention as “creeping socialism” and seek to contrast it with his own agenda.

Trump has spent the early days of the Democratic primary weighing in occasionally but his advisers privately say he is enjoying the contest and waiting until all candidates are fully declared before becoming involved.

Sabato echoed the Democratic officials fears, saying, “Democrats might also choose a weak candidate or be unable to reunite after divisive primaries,” also writing that “it’s not a given that the Democratic nominee can consolidate the votes of Trump disapprovers, particularly if a third-party candidate (Howard Schultz?) eats into the anti-Trump vote.”

The large pool of Democratic candidates has also set a stage where each must seek to differentiate themselves from the other to a base of voters polarized along the spectrum. Democratic candidates have surfaced previously anathema policy proposals, such as abolishing the Electoral College, adding seats to the Supreme Court and preemptively pledging to prosecute Trump.

The diverse array of candidates and the relentless push for differentiated media attention has led to many candidates listing further left. Hanson predicted that if Democrats embrace these left-leaning policies like “New Green Deal, open borders, abolishing ICE, reparations, permissible infanticide, 70-90 percent top income tax rates, a wealth tax, changing the Constitution to eliminate the Electoral College, voting at 16, free tuition, Medicare for all, and cancellation of $1.5 trillion in college debt” that “they will lose in 1972 or 1984 fashion.”

Democrats face the problem of not just contrasting themselves with each other but how exactly to contrast themselves with Trump.

Adams noted that “the biggest issue with Trump is you didn’t know what you were getting in 2016,” he said, adding that many of the most dire Democratic predictions that he would start a nuclear war, that he colluded with Russia, or that that the stock market would halve in value never came to fruition.”

“The Dems will either have to come up with ‘he might do this later’ or they’ll have to argue that the most successful presidency of all time wasn’t that.”

Adams also characterized the personal style of the current field of Democratic candidates as unable to match Trump in their ability to persuade the Democratic base. “The best persuaders in the Democrats are AOC, she’s the Democrat’s Trump in terms of talent,” Adams said, referencing Democratic New York Rep. Alexandria Ocasio-Cortez. Cortez, however, is only 29 years old and therefore constitutionally ineligible to run for the presidency.

So Can Trump Win Again? 

The short answer is yes, and as much depends on him as it does on his opponents. The single greatest threat to his re-election appears to have little to do with him and more to do with whether the economy will continue its remarkable run upwards throughout the 2020 election.

Democrats simultaneously are setting themselves up for a brutal slog that could cripple them ahead of what is likely to be one of the most contentious elections in modern American history.

Trump, however, is unfazed, emboldened, sure of himself and battle-ready. The day he found out special counsel Robert Mueller cleared his campaign of any collusion, he declared triumphantly: