Donald Trump has been tweetsulting Mort Zuckerman for three days now. He normally reserves this kind of prolonged rage for Megyn Kelly, so it’s worth taking a look at what’s going on here.
On the surface, Trump’s twitter tirade is about a string of recent New York Daily News covers that haven’t been kind to Trump – to put it mildly (see image below).
Mort Zuckerman, the founder of Boston Properties, also owns “New York’s hometown newspaper,” and Trump seems to allege that Zuckerman is influencing its editorial stance against him.
The Canadian-born billionaire unsuccessfully tried to sell the financially struggling publication last year. Trump went to town on that fact in a tweet tirade that began on Wednesday night, after the Daily News published a particularly harsh cover (see above). Here are the tweets, in chronological order.
Feb. 10:
Feb. 11: 
Feb. 12: 
Trump has a reputation for biting back against unfavorable coverage with personal insults, but he usually directs his rage at the reporters responsible. So why is he so keen on going after Zuckerman? A possible answer lies in their long-standing and well-known mutual animosity.
Back in 2011, the Daily News published a cover mocking Trump’s presidential aspirations (see below). Note the clown theme, which the paper has frequently returned to.
Trump responded by claiming on radio that the News was “disloyal” to him. “I saved the Daily News when Mort Zuckerman and Fred Drasner came to me years ago, and they had a huge problem, and I was able to help them save the Daily News,” he said. “And that’s the treatment I get.” Zuckerman responded by denying he ever asked Trump for help, claiming he had “no idea what [Trump’s] talking about.”
It probably doesn’t help that Zuckerman, a known Democrat, has long been critical of Trump’s politics. Take for example this August 2015 exchange on Fox News between host Neil Cavuto and Zuckerman about Trump.
Zuckerman: “Listen, I think he’s a man of considerable talents. He’s not necessarily the man I’d like to have as leader of this country, but he’s certainly someone who’s shown a good deal of talent in the real estate business. And as you know, I respect that kind of talent.”
Cavuto: “I think you’re holding back.”
Zuckerman: (laughs) “This is a fit of self-control on my part is what you’re telling me.”
What likely fans the flames on Trump’s end is that Zuckerman can legitimately claim to have had more success as a real estate investor. This is a testy subject for Trump – a businessman with a string of bankruptcies who insists on being known as a business titan for the ages.
Zuckerman isn’t the first New York real estate mogul to get caught in a public feud with The Donald. In 1988, developer Leonard Stern commissioned a documentary about Trump that questioned his real estate record. Around the same time 7 Days, a magazine owned by Stern, published a report that condo sales in the Trump Tower weren’t going well. Trump responded by threatening to sue over the film, and an unattributed report in the New York Daily News popped up claiming Stern’s wife Allison had “continually phoned Trump’s office asking for a date.”
“In the Trump view, a business rival has loosed two sets of news hounds on him, one print and one electronic,” journalist Edwin Diamond wrote in a New York magazine expose in 1989.
Stern pulled the film, which appears to have ended the feud.