New York Daily News

• 1989: Trump reportedly offered to buy the New York Daily News. “New York magazine quotes a source who says that Donald Trump has talked with the owners of the New York Daily News about buying the paper. The paper turned a small profit in 1988, after years of losing money.” (Palm Beach Post, July 28, 1989)
• 2016: The Daily News was struggling with plunging circulation and unprofitability, as Zuckerman unsuccessfully explored selling the paper. “On a recent afternoon, Jim Rich, the editor in chief of The Daily News, sat at his computer playing around with front-page headlines, a few well-chosen words that would capture the day's biggest news: Sarah Palin's endorsement of Donald Trump in the Republican presidential primary. […] Mr. Rich walked it out into the newsroom for feedback. The paper's copy chief, Jon Blackwell, proposed an alternative: ‘I'M WITH STUPID!’ […] The News, which was founded nearly 100 years ago, loses millions of dollars a year. When its owner, Mortimer B. Zuckerman, tried to sell the paper early last year, interest was light. […] Six rumor-soaked months after putting the paper on the market, Mr. Zuckerman took it off. The layoffs, which claimed dozens of reporters, came soon after in September.” (New York Times, January 30, 2016)
• The Daily News' provocative covers and headlines gave it a cultural relevance far larger than its modest readership and circulation would suggest. “As the Iowa caucus results rolled in Monday night, the wheels were surely turning in the minds of editors at the New York Daily News. Republican presidential front-runner Donald Trump - the local entry and a favorite tabloid target - was losing to Sen. Ted Cruz of Texas. Which way to go with Tuesday's cover? […] The Daily News went with a running theme: ‘Dead clown walking.’ […] It was the latest in a series of attention-grabbing covers that have shifted the conversation around the struggling paper. Just a few months ago, after an aborted sale and sweeping layoffs, The News seemed to have completed its devolution from the model of a big-city tabloid to a battered symbol of the diminished state of America's newspapers. But the recent string of covers, which were all widely shared on social media, have sent a very different message - if not about the paper's long-term financial prospects, then at least about its continuing cultural relevance.” (Washington Post, February 2, 2016)
• The Daily News gained notoriety in 2016 for its savage headlines ridiculing Donald Trump. “The New York Daily News revealed its disgust for Donald Trump with new vigor on Wednesday after Trump won the New Hampshire primary. Depicting Trump as a psycho clown on its cover, the paper compared Trump supporters to ‘mindless zombies’ and proclaimed his Granite State win the ‘Dawn of the Brain Dead.’ […] That is quite a cover. […] The truth is, this is just the latest skirmish in a years-long fight between Trump and the Daily News, much of which has played out on social media.” (Washington Post, February 10, 2016) (Washington Post, February 10, 2016)