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I know it's low hanging fruit, but 
Charismatic idiot that is really good at rousing the spirits of every fascist inside the boiling pot that is the USA, makes good deals for the top capitalists which are the tech bros in the current time, and spreads anticommunism as much as if the USSR still existed.
Yeltsin wasn't born rich, nor was he a particularly convincing social force.
I see a specific combination of factors that propelled Trump into power: immense inherited wealth, being spoiled and myopic as a result of said wealth, the profound influence of mass media and spectacle, and a populace that is facing downward mobility or some sort of societal decline.
A lot of possible comparisons are career military figures, but Trump never got his boots muddy in anything like the military.
One comparison that I often like to make (which pisses off the libs) is George Washington. Fabulous wealth that he did not "build up" himself, profound racism and classism, reactionary politics, marshaling a contingency of landowners and petit bourgeois to become the dominant political force. The biggest difference was that Washington was more literate and tacit and proper, while Trump is a showman who dives into every intrigue and controversy.
My knowledge of Yelstin is very surface level. I need to do more research on him.
I don't bother learning much about US presidents because I know they are all bad, but considering the historical significance, I should learn more about Washington. Do you have any good resources?
There are a lot of biographers that have covered him. I went to a talk a few years ago by one of them, and the objectionable things were blatant. For instance, for much of the American Revolution and the few years afterward, a lot of his efforts were to find ways to defer or entirely avoid paying the soldiers of the Continental Army.
Libs will celebrate influential historic figures and defend them by saying "the times were different". But if you have a well-formed socialist conviction, it's easy to parse through the "quirky historical facts" as actions that happen as part of a class struggle and confirm the alignment of individuals in the class struggle.
Berlusconi.
I couldn't remember his name so I typed "that corrupt Italian leader" into a search engine and came up with ...
spoiler
Silvio Berlusconi
Nah, Berlusconi fucked too much to be compared to Trump
I think certain traits are unprecedented. He may be the most anti-social leader in history. His administration is doing things that don't make sense on a societal level, like defunding research for extreme weather and disease prevention.
There are other examples of this, like Hitler's war on "Jewish physics" and Pol Pot's war on a lot of things.
Pol Pot's war on a lot of things
War on glasses
Reagan is the most obvious
Trump seems like the 2nd coming of Reagan, but in a slightly different way. Kind of like how the US compared to the British Empire.
george bush 
Napoleon III comes to mind.
“To the proletariat, the election of Napoleon meant the deposition of Cavaignac, the overthrow of the Constituent Assembly, the dismissal of bourgeois republicanism, the cessation of the June victory. To the petty bourgeoisie, Napoleon meant the rule of the debtor over the creditor. For the majority of the big bourgeoisie, the election of Napoleon meant an open breach with the faction of which it had had to make use, for a moment, against the revolution, but which became intolerable to it as soon as this faction sought to consolidate the position of the moment into a constitutional position. Napoleon in place of Cavaignac meant to this majority the monarch, in place of the republic, the beginning of the royalist restoration, a sly hint at Orléans, the fleur-de-lis hidden beneath the violets.[87] Lastly, the army voted for Napoleon against the Mobile Guard, against the peace idyll, for war.
Thus it happened, as the Neue Rheinische Zeitung stated, that the most simple-minded man in France acquired the most multifarious significance. Just because he was nothing, he could signify everything save himself.”
Marx, 18th Brumaire
Nero?
Basically came here to say this. A lot of what we’re going through is nothing new.
Trump is both Bushes is Raegan.
Alcibiades is an interesting Greek pull. Article's from before the 2016 election. I'll add some more, since there's a lot of overlap:
I am reminded of Karensky who also possessed an extraordinary stamina for flinging magnificent lies and betrayals as he held the reins of a dying state.
Wilhelm II
(this is a joke answer that i have not thought about for more than 5 seconds)
of the scream?
As IByteABit said, it’s obvious but Hitler is the clearest comparison.
I’d throw in Tsar Nicholas 2 for second place. Or maybe King George 3, didn’t he Brandonize pretty hard later in life?
I read a lot of Roman histories as a kid and these histories often had the most salacious stories about the emperors.
Like, “emperor x was a pedophile who trained young boys to nibble his nuts in the pool.” I think that was Augustus but I don’t exactly recall.
Anyway, at the time I thought these stories were obvious character assassination. The author of the history was writing to please the current emperor which meant trashing the previous dynasty.
Now, given current events, I think these histories were likely true. The rumors probably only captured a fraction of the depravity of the powerful.
Nero
I've not done much to read up on this specifically, but I have some friends who really like comparing Trump to Napoleon for some reason.
Napoleon I no, since he was a genuinely extremely talented and historically progressive figure (this term doesn't mean good, though he was better than all the monarchies of Europe). Even given the restriction of material conditions, someone like Robespierre or Hebert or Babeuf (let alone any of the useless Thermidorians) probably would not have changed things so fast or so completely.
Now Napoleon III? Absolutely.
the english have spent 2 centuries heaping trash on Napoleon, such that english speakers routinely think Napoleon was a buffoon lashing out on account of being short. an image you could compare to Trump if you squint, i guess.
'Bonapartism' is similar to Trumpism, but Trump is pretty much entirely focused on himself and has no military experience.
read 18th brumaire to find out more (about the third, to be precise)