(Jabin Botsford/The Washington Post)

There’s one group of people who probably weren’t surprised by the New York Times’s report on Tuesday that President Trump had declared more than $1 billion in losses on his income taxes from 1985 to 1994: New Yorkers who read their city’s tabloids during that period.

Over the course of a 50-image slide show that the New York Post published on the day of Trump’s 2017 inauguration — all covers depicting the man they delighted in calling “The Donald” — even the Post was forced to acknowledge this dark period, including a cover from April 1990. That year, according to the Times’s report, Trump declared that his businesses had lost more than $250 million.


(The New York Post, April 28, 1990)

Trump had gained national attention for his book “The Art of the Deal,” which came out in 1987 (a year in which Trump lost $42.2 million). The book portrayed Trump as a master of the financial universe, able to convince a resident of the frozen north that jokes about selling them ice were fresh and amusing. So when America suddenly learned that Trump was in dire straits, there was some schadenfreude to be had.

“Some people hope Trump solves his financial problems, others hope he goes bankrupt,” one pollster asked in July 1990. “Which best describes you?” About 2 in 10 said they hoped he would go bankrupt — a relatively good result.

Gallup noted that Trump was “in financial trouble and is on an allowance from his financial backers.” Nearly two-thirds said he was getting what he deserved. If he went bankrupt? About 6 in 10 said either that they didn’t care or that they would be glad.


(Philip Bump/The Washington Post)

When NBC News and the Wall Street Journal asked Americans their opinions of Trump, half had at least a somewhat negative view of him. Three percent said they viewed him very positively.


(Philip Bump/The Washington Post)

Perhaps the poll result that would cause Trump the most angst came from a Post-ABC News survey. Given both his problems and his wealth, we asked, would you trade places with Trump?

More than 8 in 10 said they wouldn’t.


(Philip Bump/The Washington Post)

In the late 1990s, Trump started to flirt with the idea of running for president, even briefly considering a run for the Reform Party nomination in the 2000 race. Gallup polled in 1999 to determine how people viewed Trump and found that 41 percent viewed him favorably and 47 percent negatively — a net minus-6 favorability.


(Philip Bump/The Washington Post)

Trump didn’t run that year. Instead, he became a TV star.

In January 2004, his show “The Apprentice” premiered. The show had the same premise as his 1987 book: Trump was fabulously wealthy, fabulously successful — and he could show you how to achieve the same status.

In its first season, “The Apprentice” was the top-rated show in the country the week of the finale, the only time it would achieve that status. But the show’s success quickly led to more seasons: a second one in 2004 and two in 2005. The second season in each year ended right before Christmas.

Gallup and its polling partners included Trump in a December 2004 poll asking whether Trump should be on Santa’s “naughty” or “nice” list. People were split, with only Democrats constituting a majority that said Trump belonged on the “nice” list.


(Philip Bump/The Washington Post)

After two more seasons of “The Apprentice,” those numbers shifted. By December 2005, a majority of all Americans said Trump belonged on the “nice” list. Majorities in every political group held that position, with the percentage of both Democrats and Republicans saying he belonged on the “nice” list climbing 10 points over the year.


(Philip Bump/The Washington Post)

Perhaps most telling was another poll from Gallup, in which the pollsters again asked how people viewed Trump.

This time, half of respondents said they viewed him favorably. On net, Trump’s favorability was plus-12, an 18-point swing from six years prior.


(Philip Bump/The Washington Post)

The rehabilitation was underway.