Donald Trump enjoyed several advantages in 2016 that he will (almost certainly) lack in 2020. In his first presidential campaign, the mogul had the benefit of running against a Democrat who was the target of an FBI investigation and Kremlin "ratfucking" operation. His status as a "change candidate" appealed to some number of disillusioned swing voters—while his status as a tabloid punch line left some number of Democrats too confident to vote. Meanwhile, he is likely to face a less demographically favorable (i.e., old and white) electorate next year than he did on the last go-round. Between 2014 and 2018, the number of eligible voters from the (right-leaning) boomer and silent generations declined by 9 million, enabling (left-leaning) Gen-Xers, millennials, and Gen-Zers to collectively outvote their elders last fall for the first time ever.
These realities—combined with the president's low approval ratings in key battleground states, his weak head-to-head numbers against potential Democratic rivals, and his exceptionally thin margin of victory in 2016—give blue Americans some cause for comfort.
But when contemplating the various ways the president's task in 2020 will be more difficult than it was in 2016, one shouldn't neglect the other side of that ledger. Incumbency will provide Trump with advantages he lacked last time out, both because voters are historically reluctant to "change horses in midstream," and because a president has access to unique resources and can effortlessly generate earned media (the Democratic nominee will not be able to divert millions of dollars from the National Park Service to fund her own Independence Day extravaganza). And if the economy does not enter recession before November of next year, Trump will also be able to credibly claim that his presidency has left the median American better off materially than she was four years ago.
But the most significant, novel advantages that Trump will have in 2020 will be a fully professional—and extraordinarily well-funded—reelection effort.
Trump's first presidential campaign raised a grand total of $350.7 million. His second just raised $105 million in the past three months alone. That's more than Barack Obama raised over the same period in 2011.
In 2016, the mogul relied primarily on his own family members to solicit online donations. The Republican National Committee already spent close to $20 million on a professional operation to cultivate such contributions. And it appears to be paying off:
Trump campaign officials said they received 725,000 individual donations online, with supporters giving an average of $48—small-donor enthusiasm that was unprecedented in Republican politics, according to a committee official, who noted it was the first time the Republican National Committee attracted a larger share of donations under $200 than the Democratic National Committee.
Meanwhile, Trump is also winning unprecedented support from the GOP's big-dollar donors, some of whom shunned (or at least, skimped on) his first campaign; by delivering tax cuts and reactionary judges, Trump has ostensibly persuaded America's wealthiest self-styled libertarians that they don't actually care that much about the rule of law.
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In 2016, Hillary Clinton outspent Trump by $235 million. The Democratic field is collectively raising a great deal of cash, but they'll be directing that ammunition against each other for another nine months at least. At this point, it appears likely that Trump will outspend his Democratic rival, and mount the first fully professional political campaign of his career.
Of course, money and professionalism aren't everything—as Clinton learned in 2016. Trump's novel weaknesses may ultimately dwarf his newfound strengths. But Democrats shouldn't bank on it.