REUTERS/Scott Audette
Among other things, Trump repeatedly called the newspaper "failing," accused it of being biased against him, and demanded an apology from the paper for criticizing him after he mocked a reporter with a physical disability.
"The New York Times, which is in huge financial difficulty, which won't make it," Trump predicted.
"Somebody will come along [and buy it], some rich guy. Maybe I'll do it, ha ha," he joked. "Some rich guy that wants to be relevant - that's rich but nobody ever heard of him, and he can't get a place a restaurant. I have a lot of friends, they call me ... they're worth $2, $3 billion: 'Don, could you do me a favor? Could you get me a place at a restaurant?"
Trump started to launch an all-out attack on The Times earlier this week, when the paper criticized him for mocking one of its reporters, Serge Kovaleski.
"We think it's outrageous that he would ridicule the appearance of one of our reporters," a Times spokeswoman told Politico.
At a Tuesday-night campaign rally, Trump impersonated the reporter supposedly retracting his 15-year-old story about the World Trade Center attacks. Trump's hand gestures appeared to many, including Kovaleski, to mock the reporter's disability that limits his hand movements.
The Republican presidential front-runner responded by firing off a raging tweetstorm and multiple statements blasting The Times and accusing the reporter of "using his disability to grandstand." Kovaleski said he's positive Trump knew about his disability from their interactions over the years, but Trump has insisted that's not the case.
Trump claimed during his Saturday rally that he was simply impersonating a generic reporter "groveling" while trying to retract an old story.
"I didn't know him," Trump said of Kovaleski, never using his name. "It's possible, probable, that I met him somewhere along the line. But I deal with reporters every day, many of them I never even see. ... He's using what he's got to such a horrible degree. I think it's disgraceful."
AP Photo/Steve Nesius
Trump also repeatedly insisted he would never mock someone with a disability.
"I don't mock people that have problems. I don't mock people that have problems, believe me. Now people mock me with my hair, but it is my hair," he said.
But at the same time, Trump took a somewhat tongue-in-cheek approach being "politically correct" at his rally. He said he had his son find "exactly the right terminology" he should use to describe people with disabilities. He quoted an unnamed website saying terms like "a disabled person," "the disabled," and "handicapped parking" should be avoided.
"Even though people have handicapped permits," Trump added to laughs. "So it's so complicated out there. It's tough. No, it's tough. And we want to be politically correct."
Trump also used his Saturday speech to issue a scathing indictment of The Times' larger business model. He mocked the newspaper for a supposedly terrible real-estate deal in midtown Manhattan, and he called The Times' purchase of The Boston Globe "one of the worst investments of all time."
"These are the people that are writing editorials criticizing me and you and everybody that believes like we believe. These are the people. These people don't have it," Trump said. "I always say, 'The failing New York Times.' It'll probably be out of business pretty soon."
Trump closed out that segment of his speech by demanding an apology from The Times, which didn't immediately respond to a request for comment from Business Insider.
"I think The New York Times, frankly, should give me an apology. I do," he said. "And I'd love to have the apology before they go out of business."