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

Ben Weiss

Influencer who attended Trump’s memecoin dinner says he got a ‘Walmart steak’—and no access to the president

https://fortune.com/crypto/2025/05/23/trump-memecoin-dinner-nicholas-pinto-bad-food/?itm_source=parsely-api

Alan Suderman

The Associated Press

15 years ago, a software developer paid for two pizzas with 10,000 bitcoin. Those pies would be worth $1.1 billion today

https://fortune.com/article/pizza-bitcoin-day-story-laszlo-hanyecz-papa-johns-pizzas-value/?itm_source=parsely-api

Dave Smith

Telegram's CEO built two dominant social networks from scratch before 40 and has fathered more than 100 biological children. He's also facing up to 10 years in prison

https://fortune.com/2025/05/22/pavel-durov-life-career-telegram-vk-children-arrest-legal-issues/?itm_source=parsely-api

Lila MacLellan

Target reports dismal earnings amid DEI 'headwinds' and says two C-suite women leaders are on the way out

https://fortune.com/article/target-earnings-drop-tariffs-dei-headwinds-c-suite-shakeup/?itm_source=parsely-api

Stuart Dyos

The jet Qatar gave Trump is valued around $400 million. It might cost taxpayers $1 billion just to upgrade it to presidential standards

https://fortune.com/2025/05/23/airplane-qatar-air-force-one-cost/?itm_source=parsely-api

Amanda Gerut

Supreme Court gives Trump unprecedented power to fire regulators—except Federal Reserve Chair Jerome Powell

https://fortune.com/article/supreme-court-trump-fire-regulators-fed-powell/?itm_source=parsely-api