A year ago for this newspaper, I wrote a piece headlined “2019 will be the worst year of Trump’s life.” Lately, I’ve been feeling a bit smug about my prescience. A wiser man might retire from the prognostication game on that high note, but instead I’m going to double down with a new prediction: 2020 will be the worst year of Trump’s life.

Last year’s foresight wasn’t that hard, in retrospect. It seemed likely, given what we’d already seen, that Trump was going to create problems for himself on a scale unmatched in his previous life. No one foresaw the exact nature of his misdeeds — that he’d threaten to withhold military aid from Ukraine in order to pressure leaders there to investigate his campaign rival — but it was pretty easy to see that the year was likely to produce more scandals, failures and defeats.

The coming year presents many more uncertainties. There’s the election, of course, and the Democrats aren’t seen as having a surefire winner.

President Trump, on the other hand, is a strong campaigner and more determined to win than ever. If he doesn’t, he spends the rest of his life as a loser — the worst thing you can be in Trump world. Republicans have worked tirelessly to create new restrictions on voting by Democrats, and the bots and dirty tricks that helped sway the last election will undoubtedly be reprised.


There is also the possibility that the Democrats will self-destruct at their convention. Maybe vote suppression by Republicans will succeed. Maybe Tulsi Gabbard will run as a third-party candidate and draw enough votes in a few key states to give the election to Trump. Maybe Trump will lose the popular vote by millions — again — but squeak through in the electoral college by a few thousand.

But I don’t think he can win this time. Despite being the most powerful political figure in America for the last three years, Trump hasn’t done anything to expand his base. And the Democrats will never again make the mistakes Hillary Clinton made in Pennsylvania, Michigan and Wisconsin.

The starting point for 2020 is the fact that the Democratic base is considerably larger than the Republican base. Almost half of registered voters (48%) say they are certain they will vote against Trump, while only a third (34%) say they are certain they will vote for him.

The Democratic strategist and pollster Stan Greenberg has a whole book about why Trump will lose (with the great title R.I.P. G.O.P.). He asked voters in a 2016 election day poll whether they could handle an unexpected expense of $500. A majority of unmarried women said they could not. They are unlikely to agree with Trump’s claims about his tax cut benefiting everybody, and unmarried women make up a quarter of the potential electorate.


On many of the issues Americans care most about, Trump is consistently on the wrong side. An increasing majority of people, as Greenberg points out, believe “immigration benefits our country,” up from 50% in 2016 to 65% today. An increasing majority — now more than 60% — believe that the government should play a bigger role in addressing our problems, especially in healthcare. Free college tuition and a wealth tax have widespread support.

Of course 2016 showed that we need to look beyond the national polls, and focus on the swing states. But there, too, the news is encouraging. In Pennsylvania, Michigan and Wisconsin, since Trump took office, his net approval ratings, which started out on the plus side, have fallen — disastrously. In Pennsylvania they decreased by 17 points, in Wisconsin by 20 points, in Michigan by 22 points. In the midterm voting, those three swing states all elected Democrats in 2018. Wisconsin elected a Democratic governor to replace a Republican, and reelected a Democratic senator; Pennsylvania reelected a Democratic governor and Democrats there took three House seats away from Republican incumbents. In Michigan, which the Democrats lost to Trump by 11,000 votes, the Democrats had a huge victory in 2018, sweeping the elections for governor and senator and flipping two House seats. Voters also banned gerrymandering and created automatic voter registration, which together will bear fruit in 2020. All this explains why I’m quite certain we’ll be free at last from Donald Trump on Jan. 20, 2021.

Honesty compels me, however, to recall another article I wrote in the past. This one was for The Nation in June of 2016, and it was headlined: “Relax, Trump Can’t Win.”

Jon Wiener is professor of history emeritus at UC Irvine and a contributing editor at The Nation, where he hosts the podcast “Start Making Sense.”