Often we forget how impressive his 1988 victory was. (Declaration of interest: I worked in the 1988 Bush campaign.)
In 1988, Bush got a higher share of both the popular vote and the electoral vote than any candidate since then, including Barack Obama in 2008:
Obama won under more favorable circumstances. The other party had been in power for two terms and was presiding over the worst economic crisis since the Great Depression.
Bush was the vice president of an administration that had been in power for eight years, so the "time for a change" mentality worked against him. No sitting vice president had been won the White House since Martin Van Buren. The economy was growing and the Cold War was winding down, but Bush had to deal with the aftermath of the 1987 market meltdown and the Iran-Contra scandal. For a long time, many thought that he would lose.
In May 1988, E.J. Dionne reported at The New York Times:
Michael S. Dukakis is capitalizing on deep public doubts about Vice President Bush and the Reagan Administration's handling of key issues and has emerged as the early favorite for the Presidential election in November, according to the latest New York Times/CBS News Poll.
Mr. Dukakis, the probable Democratic nominee, ran ahead of Mr. Bush, the almost certain Republican candidate, by 49 percent to 39 percent among 1,056 registered voters.
The survey, conducted May 9-12, represented a significant advance for Mr. Dukakis since a Times/CBS News Poll in March when Mr. Bush had 46 percent and Mr. Dukakis had 45 percent.
In the latest poll, Governor Dukakis of Massachusetts led in all regions, but he ran especially well in the Northeast and Middle West. The poll found Mr. Dukakis with very substantial advantages over Mr. Bush among women, union members, Roman Catholics and blacks/A couple of months later, the Times reported:
In the aftermath of the Democratic National Convention, the party's nominee, Michael S. Dukakis, has expanded his lead among registered voters over Vice President Bush, the probable Republican nominee, according to a Gallup Poll.
This was among the findings of a national public opinion poll of 948 registered voters conducted late last week for Newsweek magazine by the Gallup Organization. The telephone interviews took place on July 21, which was the last night of the convention, and on the night after that.
Fifty-five percent of the 948 registered voters interviewed in the poll said they preferred to see Mr. Dukakis win the 1988 Presidential election, while 38 percent said they preferred to see Mr. Bush win. The poll had a margin of sampling error of plus or minus four percentage points.
In the end, however, Bush not only won comfortably, but he carried states that we today consider to be deep blue, including California, Illinois, Delaware, Maryland, Connecticut, New Jersey, and Vermont.