I had no idea.
September 14, 1987. Garry Trudeau drew the first Doonesbury comic strip that would feature Donald Trump. For Trudeau, Trump became the gift that kept on giving.

Trudeau has compiled that gift into a book, published this summer. From the subsequent press tour, I give you “Trudeau on Trump”:
“Even though he’s changed wives twice and party affiliation five times since I’ve been watching him, the underlying personality disorder has remained remarkably stable.”[1]

“Trump is beyond traditional parody. His demeanor, speech and behavior are so over the top, there’s no point in trying to exaggerate it. That only leaves you with framing, somehow recontextualizing his repugnant behavior so it’s thrown into high relief. For instance, I did a Sunday page in which ‘The Donnie’ takes down the other kids in a middle school cafeteria. It’s the same language he normally uses, but the strip shows you just how unserious and pathetic his name-calling really is.”[2]

“Here’s what the people who love Trump don’t understand: He doesn’t love them back. I figured they’d be on to him by now. These are folks who feel anxious and left behind by the new economy. Many are struggling. Trump has a word for such people: losers. And he’s never had time for losers.”[3]
How did Trudeau become aware of Trump?
“[H]e was inescapable in New York — but his ‘open letter’ in 1987 to the American people was the tipping point,” Trudeau told the NY Times.
Open letter?
Yes, on September 2, 1987, Donald Trump, 41, paid $94,801 ($200,823.73 in 2016 dollars) to run a full page ad in The Boston Globe, The New York Times, and The Washington Post.
In that ad, he showcases the workings of a mind that would later call for a wall between the U.S. and Mexico, with Mexico footing the bill. The 1987 argument: that the U.S. should bill Western Europe and Japan for the cost of “safeguard[ing] the passage of oil tankers in the Persian Gulf.”

At least his foreign policy positions are consistent.
So are his media tactics.
In the wake of the 1987 newspaper ads, a Trump spokesperson stated:
“There is absolutely no plan to run for mayor, governor or United States senator. He will not comment about the Presidency.”[4]
The statement was concurrent with a report that Trump would be traveling to New Hampshire “in response to an invitation from Mike Dunbar, a Republican who is running a ‘draft Donald Trump‘ [for President] movement.” [Note: George H.W. Bush, who was Reagan’s VP in 1987, was the 1988 GOP nominee.]
“He did, however, travel to Moscow in July, where he met with the Soviet leader, Mikhail S. Gorbachev. The ostensible subject of their meeting was the possible development of luxury hotels in the Soviet Union by Mr. Trump…
“In addition to the Fifth Avenue tower that bears his family name, Mr. Trump’s visibility has been increased of late by a raging feud with Mayor Koch over how much government subsidy should be provided to encourage Mr. Trump’s planned Television City complex along the Hudson River.”[5]
Trudeau features Trump quotes about himself in the book, noting in the preface and in interviews that Trump’s early appreciation for attention quickly turned to disdain.

You need to buy this book!
2 replies on “30 years of Donald Trump, courtesy of Doonesbury”
30 years of Donald Trump, courtesy of Doonesbury
https://t.co/GXUFcWgdXV via @kathyg
Doonesbury has documented Trump’s flirtation with politics like no other. https://t.co/zm3WNVPpR2 https://t.co/0DMWy9hRAZ