The 5 best Donald Trump headlines of all time

Ryan Daly

For as long as Donald Trump has been making deals, he has been making headlines. The 69-year-old billionaire was arguably the <a href="https://fortune.com/2015/08/07/gop-debate-businesses/">star of the Republican debate</a> held on August 6, leading as he has in both the polls and the hot rhetoric. Who won is a <a href="http://www.nytimes.com/2015/08/08/upshot/bush-and-trump-arent-among-the-gop-debate-winners.html?_r=0&amp;abt=0002&amp;abg=1">matter of debate</a>; but, the name &#8220;Trump&#8221; graced many headlines on the morning after the 10-candidate forum. Here are Trump&#8217;s best tabloid headlines from over the years:<div class="paywall-selector"></div><div class="paywall">
5. I&#8217;ll start in 1990. Spy Magazine&#8216;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.
<a href="https://fortune.com/2015/08/07/donald-trump-news/attachment/1298467597/" rel="attachment wp-att-1233563"><img loading="lazy" decoding="async" class="aligncenter size-full wp-image-1233563" src="https://content.fortune.com/wp-content/uploads/2015/08/1298467597.jpg?quality=80" alt="1298467597" width="495" height="650" /></a>coverjunkie.com
4. Perhaps unsurprisingly, New York&#8217;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.
<a href="https://content.fortune.com/wp-content/uploads/2015/08/chs6ntqwgaaswmw.jpg?quality=80"><img loading="lazy" decoding="async" class="aligncenter size-full wp-image-1233564" src="https://content.fortune.com/wp-content/uploads/2015/08/chs6ntqwgaaswmw.jpg?quality=80" alt="CHs6NtQWgAAswMW" width="600" height="798" /></a>frontiersmedia.com
3. This 1990s New York Post Trump cover makes its way to number 3 with a story surrounding Marla Trump&#8217;s &#8220;best sex I&#8217;ve ever had quote.&#8221; This cover&#8217;s fusion of a smug Trump and a caption you only wish he had said himself merits noting.
<a href="https://content.fortune.com/wp-content/uploads/2015/08/new-york-post.png"><img loading="lazy" decoding="async" class="aligncenter size-full wp-image-1233565" src="https://content.fortune.com/wp-content/uploads/2015/08/new-york-post.png" alt="new-york-post" width="406" height="497" /></a>turtlemeat.com
2. The Post&#8216;s &#8220;Don Voyage&#8221; cover was a comment on Trump&#8217;s Criticism of John McCain. This cover sports an eccentrically cartoonish photoshopping job of an adrift Trump and a simple, yet appropriate name pun.
<a href="https://fortune.com/2015/08/07/donald-trump-news/getimage-3/" rel="attachment wp-att-1233566"><img loading="lazy" decoding="async" class="aligncenter size-full wp-image-1233566" src="https://content.fortune.com/wp-content/uploads/2015/08/getimage.jpg?quality=80" alt="getimage" width="687" height="584" /></a>pressdisplay.com
1. Taking the number 1 spot is a headline reportedly appearing in Scotland&#8217;s The Daily Record. The story covers Trump&#8217;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 &#8220;borrowed&#8221; from the wealth of internet Trump puns—and image earns it number 1.
<a href="https://content.fortune.com/wp-content/uploads/2015/08/scottishnewsheadline-thumb-1000x750-117216.jpg?quality=80"><img loading="lazy" decoding="async" src="https://content.fortune.com/wp-content/uploads/2015/08/scottishnewsheadline-thumb-1000x750-117216.jpg?quality=80" alt="ScottishNewsHeadline-thumb-1000x750-117216" width="1000" height="750" class="aligncenter size-full wp-image-1233567" /></a>theatlantic.com</div>

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

Donald Trump: The Best Headlines

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The 5 Best Donald Trump Headlines of All Time

Donald Trump: The Best Headlines | Fortune

Paolo Confino

BlackRock CEO Larry Fink says almost everyone he talks to is ‘more anxious about the economy than any time in recent memory’

https://fortune.com/2025/03/31/blackrock-larry-fink-annual-letter-economy-uncertainty-tariffs-recession/?itm_source=parsely-api

Sydney Lake

Roughly half of Gen Z workers say they don't want to return to the office because it means they can't binge-watch their favorite TV shows during work anymore

https://fortune.com/2025/04/01/gen-z-workers-streaming-while-working-from-home-survey/?itm_source=parsely-api

Retail Brew

Target can't get its footing after its DEI program demise and a 40-day boycott against the retailer. Foot traffic at stores is down for the eighth consecutive week

https://fortune.com/2025/04/01/target-dei-demise-boycott-foot-traffic-down-eighth-consecutive-week/?itm_source=parsely-api

Sasha Rogelberg

DOGE's access to the payroll system of 276,000 federal employees puts government on path to have 'unprecedented power and control' over Americans' information, experts say

https://fortune.com/2025/04/01/doge-access-payroll-system-privacy-cybersecurity-concerns/?itm_source=parsely-api

HR Brew

A recruiter agreed to interview what seemed like a desperate job candidate. Then she realized it was a deepfake— 'It was very creepy'

https://fortune.com/2025/04/01/recruiter-deepfake-interview-tricked/?itm_source=parsely-api

Beatrice Nolan

Elon Musk's DOGE is undermining the Social Security Administration's technology and operations, former White House official says

https://fortune.com/2025/04/01/elon-musk-doge-social-security-benefits-cut-breaking-technology-former-white-house-official/?itm_source=parsely-api