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The worst man in the world

Ken Jennings Posted by Ken Jennings.

Ken Jennings, Ph.D. is a senior partner at VentureWorks and a managing partner at Third River Partners, a consultancy that specializes in leadership development and strategy execution.

The worst man in the world

When Time magazine named President-elect (!!!) Donald Trump its “Person of the Year” last week, I tweeted

That’s not a joke, as you might have guessed if you recall the steady stream of Spy magazine nostalgia on this blog over the years. The late, lamented satire magazine always ran a year-in-review piece called “The Spy 100,” a rundown of the “most annoying, alarming, and appalling” people, places, and things of the year. I felt confident that Trump was the only person to earn both magazine honors, but wanted to double-check that Spy never anointed George H. W. Bush, on whom they were always way harder even than they were on Reagan. So I hit the back issues to make sure.

At first I was surprised to see that Trump never topped any of the ’80s lists, during the magazine’s early “funny years.” Even though he wasn’t in the #1 spot, though, he was ever-present. Spy loved hating Trump. He appears no fewer than five times on the 1988 list, for example (in different roles, including–presciently!–“Donald Trump, Candidate”). And on the 1989 list, Trump never appeared, but the 100 other entries were each assigned a TrumpScore, measuring the closeness of their relationship to Spy‘s great orange whale. (The TrumpScore, T, was added to the official Spy 100 equation, alongside other variables like L, Inherent Loathsomeness, and M, Misdeeds.)

I had pretty much given up when I got to 1995, and was surprised to find Trump, at a low point in relevance, for some reason topping the list! I assume Spy‘s new bosses were trying to recapture the glory days of their 1980s Trump feud.

Since there’s no online list anywhere that I could find, here as a public service are the “winners” at the top of the Spy 100 during every year of the magazine’s lifespan. You can really see the 1992-1993 dividing line when new editorial took over and the magazine stopped being good.

1987 Ivan Boesky
1988 Al Sharpton
1989 Lee Atwater
1990 “S & L Hell” (the savings and loan crisis)
1991 “New World Disorder” (post-Cold War and -Gulf War mishegas)
1992 H. Ross Perot
1993 Jerry Seinfeld
1994 Forrest Gump (though O.J. Simpson merited a special entry as “Off the Scale”)
1995 Donald Trump
1996 Friends
1997 Ellen DeGeneres