When people read 1984, they don't side with the totalitarian government. The idea of oppression of basic freedoms and enforcing thought crimes aren't particularly appealing, especially to an American audience who generally operate under the assumption that the bill of rights will be upheld.
So why does it not immediately raise some red flags when the president of the free world praises leaders whose style of ruling can only be described as Orwellian? It's not a one-off thing either, and there is a recurrent theme of praise for people who definitely don't deserve it for doing things that definitely don't deserve it.
Before delving into the implications of the presidential endorsement of real-world Bond villains, let's actually review who he's expressed admiration for, and what it is that he admires. He seems to somehow only reserve his genuine unprovoked support for some of the most oppressive leaders of the modern era, which is always comforting.
Let's start with Trump's running mate (allegedly, of course), Vladimir Putin. The former KGB operative, surveillance specialist, and part-time geneva convention bad boy is held in quite high regards by the business mogul president. It turns out real recognizes real in the world of securing your power and influence at the expense of those whom you are tasked with taking. Trump has applauded Putin for his strength of leadership, and heavy-handedness, even directly defending the Russian president when he was accused (rightly) of being a killer. "There are a lot of killers. Do you think our country is so innocent? Do you think our country is so innocent?", he has said after being grilled on his red fisted pal. Considering we've been passively at each other's throats for the last 25+ years, it's odd that the president would not only defend him but defend his obtuse tactics for quelling dissent. His affinity for heavy-handed approaches doesn't stop there, however, as he's given Saddam Hussein credit on multiple occasions for being "great at eliminating terrorists". Saddam was a war criminal and promoted state-sponsored acts of terrorism. Saddam awarded $50,000 to families of suicide bombers who acted against Israel at one point. Moreover, he executed people acting against the state, which would effectively designate them as terrorists. This wouldn't exactly work in the US, however, as due process and basic human rights get in the way of murder on the flip of a dime. Tedious, I know.
He has commended the actions of the government during the famous Tiananmen Square riots, which quite literally every person with a soul condemned as a civil rights travesty. What begins to emerge is a clear image, not of a person with firm moral beliefs, rather an imperious worldview and ruthless modus operandi.
Most recently, he heaped praise on the North Korean dictator Kim Jong Un. While no more upsetting than any other ill-advised fondness for tyrants, this one sticks out on the basis that the US and North Korea are locked in a conflict with nuclear repercussions, and is committing every human rights violation in the book as you read this. At this point, he's basically complementing his opponents "strong, masculine grip" in the clinch rather than vying for advantage.
The thing that is so troubling about all of this, simply put, is that Trump seems to hold dogmatic leadership in high regard, as something to strive towards. Trump's admiration for them, like most things in his life, stems from his ego. They run countries like he runs businesses; not very well, but still doing quite well for themselves. He doesn't have respect for the basic rules of democratic leadership that our republic is built on. If he had it his way, you don't think he'd act in the same manner if given the opportunity. This kind of megalomaniacal thinking just ain't gonna cut it, Bubba.