Arts & Entertainment

The 5 best Donald Trump headlines of all time

Donald Trump has been the subject of some notable headlines over the years

Ryan DalyAugust 7, 2015

For as long as Donald Trump has been making deals, he has been making headlines. The 69-year-old billionaire was arguably the star of the Republican debate held on August 6, leading as he has in both the polls and the hot rhetoric. Who won is a matter of debate; but, the name “Trump” graced many headlines on the morning after the 10-candidate forum. Here are Trump’s best tabloid headlines from over the years:

5. I’ll start in 1990. Spy Magazine‘s cover featuring an infantilized Trump throwing a temper tantrum demonstrates a younger, up-and-coming Trump. The story clipped together the turmoil he endured in the 90s like failed land acquisitions and chapter 11 filings.

coverjunkie.com

4. Perhaps unsurprisingly, New York’s liberal-leaning daily The Daily News has not typically been a fan of Trump. The tabloid pulled no punches when he announced his candidacy earlier this year.

frontiersmedia.com

3. This 1990s New York Post Trump cover makes its way to number 3 with a story surrounding Marla Trump’s “best sex I’ve ever had quote.” This cover’s fusion of a smug Trump and a caption you only wish he had said himself merits noting.

turtlemeat.com

2. The Post‘s “Don Voyage” cover was a comment on Trump’s Criticism of John McCain. This cover sports an eccentrically cartoonish photoshopping job of an adrift Trump and a simple, yet appropriate name pun.

pressdisplay.com

1. Taking the number 1 spot is a headline reportedly appearing in Scotland’s The Daily Record. The story covers Trump’s attempt to sue the Scottish government in 2013 for a wind farm being built too close to his golf course. Its combination of clever punning—though likely “borrowed” from the wealth of internet Trump puns—and image earns it number 1.

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theatlantic.com