Trump's populist attacks against our (classically) liberal world order is indeed cause for concern. His assault on the truth is indeed a bit Orwellian. But it's op-eds like this one at CNN that are part of the problem.
While the author of the op-ed spends much time talking about his dogs ("Winston", "Julia"), and how much he hates Trump, he spends little time on the core thesis "Orwellianism". When he does, it's mostly about old political disagreements. For example, the op-ed calls Trump's cabinet appointees Orwellian simply because they are Republicans:
He has provided us with Betsy DeVos, a secretary of education nominee who is widely believed to oppose public education, and who promotes the truly Orwellian-sounding concept of "school choice," a plan that seems well-intentioned but which critics complain actually siphons much-needed funds from public to private education institutions.
Calling school-choice "Orwellian" is absurd. Republicans want to privatize more, and the Democrats want the state to run more of the economy. It's the same disagreement that divides the two parties on almost any policy issue. When you call every little political disagreement "Orwellian" then you devalue the idea. I'm Republican, so of course I'd argue that the it's the state-run education system giving parents zero choice that is the thing that's Orwellian here. And now we bicker, both convinced that Orwell is on our side in this debate. #WhatWouldOrwellDo
If something is "Orwellian", then you need to do a better job demonstrating this, making the analogy clear. For example, last year I showed how in response to a political disagreement, that Wikipedia and old newspaper articles were edited in order to conform to the new political reality. This is a clear example of Winston Smith's job of changing the past in order to match the present.
But even such clear documentation is probably powerless to change anybody's mind. Whether "changing the text of old newspaper articles to fit modern politics" is Orwellian depends entirely on your politics, whether the changes agree with your views. Go follow the link [*] and see for yourself and see if you agree with the change (replacing the word "refugee" in old articles with "asylee" instead).
It's this that Orwell was describing. Doublethink wasn't something forced onto us by a totalitarian government so much as something we willingly adopted ourselves. The target of Orwell's criticism wasn't them, the totalitarian government, but us, the people who willingly went along with it. Doublethink is what people in both parties (Democrats and Republicans) do equally, regardless of the who resides in the White House.
Trump is an alt-Putin. He certainly wants to become a totalitarian. But at this point, his lies are juvenile and transparent, which even his supporters find difficult believing [*]. The most Orwellian thing about him is what he inherits from Obama [*]: the two Party system, perpetual war, omnipresent surveillance, the propaganda system, and our nascent cyber-police-state [*].
Yes, people should read 1984 in the age of Trump, not because he's created the Orwellian system, but because he's trying to exploit the system that's already there. If you believe he's Orwellian because he's Republican, as the foolish author of that CNN op-ed believes, then you've missed the point of Orwell's novel completely.
Bonus: Doing a point-by-point rebuttal gets boring, and makes the post long, but ought to be done out of a sense of completeness. The following paragraph contains the most "Orwell" points, but it's all essentially nonsense:
We are living in this state of flux in real life. Russia was and likely is our nation's fiercest rival, yet as a candidate, President Trump famously stated, "Russia, if you're listening, I hope you're able to find the 30,000 [Clinton] emails that are missing." He praises Putin but states that perhaps he may not actually like him when they meet. WikiLeaks published DNC data alleged to have been obtained by Russian operatives, but the election was not "rigged." A recount would be "ridiculous," yet voter fraud was rampant. Trusted sources of information are "fake news," and somehow Chelsea Manning, WikiLeaks' most notable whistleblower, is now an "ungrateful traitor."Trump's asking Russia to find the missing emails was clearly a joke. Trump's speech is marked by exaggeration and jokes like this. That Trump's rivals insist his jokes be taken seriously is the problem here, more than what he's joking about.
The correct Orwellian analogy to draw here is is the Eurasia (Russia) and Eastasia (China) parallels. Under Obama, China was a close trading partner while Russia was sanctioned for invading the Ukraine. Under Trump, it's China who is our top rival while Russia/Putin is more of our friends. What's Orwellian is how polls [*] of what Republicans think of Russia have gone through a shift, "We've always been at war with Eastasia".
The above paragraph implies Trump said the election wasn't "rigged". No, Trump still says the election was rigged, even after he won it. [*] It's Democrats who've flip-flopped on their opinion whether the election was "rigged" after Trump's win. Trump attacks the election system because that's what illiberal totalitarians always do, not because it's Orwellian.
"Recounts" and "fraudulent votes" aren't the same thing. Somebody registered to vote, and voting, in multiple states is not something that'll be detected with a "recount" in any one state, for example. Trump's position on voter fraud is absurd, but it's not Orwellian.
Instead of these small things, what's Orwellian is Trump's grander story of a huge popular "movement" behind him. That's why his inauguration numbers are important. That's why losing the popular vote is important. It's why he keeps using the word "movement" in all his speeches. It's the big lie he's telling that makes him Orwellian, not all the small lies.
Trusted sources of news are indeed "fake news". The mainstream media has problems, whether it's their tendency to sensationalism, or the way they uncritically repeat government propaganda ("according to senior government officials") regardless of which Party controls the White House. Indeed, Orwell himself was a huge critic of the press -- sometimes what they report is indeed "fake news", not simply a mistake but something that violates the press's own standards.
Yes, the President or high-level government officials have no business attacking the press the way Trump does, regardless if they deserve it. Trump indeed had a few legitimate criticism of the press, but his attacks have quickly devolved to attacking the press whenever it's simply Truth disagreeing with Trump's lies. It's all attacks against the independent press that are the problem, not the label "fake news".
As Wikipedia documents, "the term "traitor" has been used as a political epithet, regardless of any verifiable treasonable action". Despite being found not guilty of "aiding the enemy", Chelsea Manning was convicted of espionage. Reasonable people can disagree about Manning's action -- while you may not like the "traitor" epithet, it's not an Orwellian term.
Instead, what is Orwellian is insisting Manning was a "whistleblower". Reasonable people disagree with that description. Manning didn't release specific diplomatic cables demonstrative of official wrongdoing, but the entire dump of all cables going back more than a decade. It's okay to call Manning a whistleblower (I might describe her as such), but it's absurd to claim this is some objective truth. For example, the Wikipedia article [*] on Chelsea Manning documents several people calling her a whistleblower, but does not itself use that term to describe Manning. The struggle between objective and subjective "Truth" is a big part of Orwell's work.
What I'm demonstrating here in this bonus section is the foolishness of that CNN op-ed. He hates Trump, but entirely misunderstands Orwell. He does a poor job pinning down Trump on exactly how he fits the Orwellian mode. He writes like somebody who hasn't actually read the book at all.