Alas, the huge question in the Trump–Reagan comparison is the likelihood of a second term.
To that end, Trump lacks something particularly notable compared to Reagan. It’s hard for him to identify a single defining accomplishment that resonates with a majority of Americans. To be fair, that’s true for many presidents who have sought a second term. Barack Obama and Bill Clinton had virtually no accomplishments, but they squeaked by. Reagan was unique going into his second term. He was celebrated for the “Reagan reversal,” for resurrecting “Morning in America,” and for his complete turnaround of the malaise and misery index of the Carter–Ford years, the Watergate and Vietnam syndromes, and much more. He was so enormously popular in 1984 that he crushed the Electoral College 525 to 13. The Reagan tax cuts alone were so dramatic that he was identified with them.
Donald Trump’s challenge is producing a similar signature accomplishment, something even his most loyal supporters struggle to find. They, for instance, expected him to build a massive border wall, which hasn’t happened. The economy is good, and the amount of deregulation has been remarkable, but the regulatory state isn’t exactly a sexy campaign issue. Trump needs something big that Americans across the spectrum can applaud as unique, bold, and memorable. (How about abolishing the IRS?)
What would Ronald Reagan think of Donald Trump? He would be impressed by many of the conservative policy accomplishments in Trump’s first three years. He would be even more impressed if Trump, like him, manages to get reelected in a landslide.