--- title: Donald Trump: The Best Headlines description: Donald Trump has been the subject of some notable headlines over the years canonical: https://time.com/3988888/donald-trump-headlines/ author: TIME article:opinion: false article:content_tier: free article:published_time: 2015-08-07T15:10:00.000Z article:modified_time: 2026-05-11T04:50:37.302Z article:section: Business og:title: The 5 Best Donald Trump Headlines of All Time og:description: Funny, sarcastic, but are they accurate? og:url: https://time.com/3988888/donald-trump-headlines/ og:site_name: TIME og:image: https://static.time.com/v3/assets/bltea6093859af6183b/blt9a8098e4214dfdc7/69885e540b72e32fc16e54ab/donald-trump6.jpg?branch=production&width=3840&quality=75&auto=webp&crop=16:9 og:image:width: 1200 og:image:height: 675 og:image:alt: Donald Trump og:type: article twitter:card: summary_large_image twitter:title: The 5 Best Donald Trump Headlines of All Time twitter:description: Funny, sarcastic, but are they accurate? twitter:image: https://static.time.com/v3/assets/bltea6093859af6183b/blt9a8098e4214dfdc7/69885e540b72e32fc16e54ab/donald-trump6.jpg?branch=production&width=3840&quality=75&auto=webp&crop=16:9 ---  # These Are the 5 Best Donald Trump Headlines Ever by [Fortune](/author/fortune/) and [Ryan Daly](/author/ryan-daly/) Aug 7, 2015 3:10 PM CUT  Real estate tycoon Donald Trump flashes the thumbs-up as he arrives on stage for the start of the prime time Republican presidential debate at the Quicken Loans Arena in Cleveland, on August 6, 2015 Real estate tycoon Donald Trump flashes the thumbs-up as he arrives on stage for the start of the prime time Republican presidential debate at the Quicken Loans Arena in Cleveland, on August 6, 2015Mandel Ngam—AFP/Getty Images by [Fortune](/author/fortune/) and [Ryan Daly](/author/ryan-daly/) Aug 7, 2015 3:10 PM CUT 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](http://fortune.com/2015/08/07/gop-debate-businesses/ "undefined") held on August 6, leading as he has in both the polls and the hot rhetoric. Who won is a [matter of debate](http://www.nytimes.com/2015/08/08/upshot/bush-and-trump-arent-among-the-gop-debate-winners.html?%5Fr=0&abt=0002&abg=1 "undefined"); but, the name “Trump” grace 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 un 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. 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. 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. ```json [{"@context":"https://schema.org","@type":"NewsArticle","@id":"https://time.com/3988888/donald-trump-headlines/","mainEntityOfPage":{"@type":"WebPage","@id":"https://time.com/3988888/donald-trump-headlines/"},"headline":"These Are the 5 Best Donald Trump Headlines Ever","datePublished":"2015-08-07T15:10:00.000Z","dateModified":"2026-05-11T04:50:37.302Z","description":"The billionaire has been the subject of more than a few clever headlines","url":"https://time.com/3988888/donald-trump-headlines/","keywords":["Media","debate","Donald Trump","newspapers"],"thumbnailUrl":"https://static.time.com/v3/assets/bltea6093859af6183b/blt9a8098e4214dfdc7/69885e540b72e32fc16e54ab/donald-trump6.jpg?branch=production&width=1200&quality=75&auto=webp&crop=1200:675&height=675","author":[{"@type":"Person","name":"Fortune","jobTitle":null,"url":"https://time.com/author/fortune/"},{"@type":"Person","name":"Ryan Daly","jobTitle":null,"url":"https://time.com/author/ryan-daly/"}],"articleSection":"Business","image":[{"@type":"ImageObject","url":"https://static.time.com/v3/assets/bltea6093859af6183b/blt9a8098e4214dfdc7/69885e540b72e32fc16e54ab/donald-trump6.jpg?branch=production&width=1200&quality=75&auto=webp&crop=1200:675&height=675","width":1200,"height":675,"headline":"Donald Trump","caption":"Donald Trump","creditText":"Mandel Ngam—AFP/Getty Images","representativeOfPage":true}],"publisher":{"@type":"Organization","name":"Time","url":"https://time.com/","logo":{"@type":"ImageObject","url":"https://time.com/images/logo.png","width":528,"height":156},"foundingDate":"March 3, 1923","sameAs":["https://www.facebook.com/time","https://www.instagram.com/time/?hl=en","https://twitter.com/time","https://www.pinterest.com/timemagazine"]}},{"@context":"https://schema.org","@type":"BreadcrumbList","itemListElement":[{"@type":"ListItem","position":1,"item":{"@id":"/section/business/","name":"Business"}},{"@type":"ListItem","position":2,"item":{"@id":"/tag/media/","name":"Media"}},{"@type":"ListItem","position":3,"item":{"@id":"https://time.com/3988888/donald-trump-headlines/","name":"These Are the 5 Best Donald Trump Headlines Ever"}}]}] ```