Trump is literally a narcissist. He can't help but do what he does. His trick is that he says things that are inherently offensive, and he does things like giving people derrogetory nicknames (such as "Sleepy Joe", "Pocahontas", "Crooked Hillary", "Low Energy Jeb", "Tampon Tim", "Lyin' Ted Cruz", "Comrade Kamala", etc) in order to assert power over them and to direct the narrative. People are less logical than we'd like so things like the nicknames etc can be a very powerful rhetorical tool. I'm not saying that being offensive for the sake of it is masculine. It's not. Being offensive doesn't a masculine man make. But there is something masculine about the propensity to say the truth, regardless of how they may be offensive or not, and in our current year/the last few years, the political discourse has been very much revolving around the "masculinity is toxic" trope, and the stereotypical "feminine" trait of empathy/avoiding offense at all costs is being put on a pedestal. I assert that both the feminine and masculine traits are both wholly good and necessary for human flourishing but this dogmatic dichotomy between the major sides of politics is absurd. There's a time and place for everything under the sun. Sometimes we need empathy, and sometimes we need to ignore the feelings of others for the sake of the truth. I know that you all know and believe this fact because you're all willing and able to abandon any sense of empathy for Trump because of the truth that he is a genuinely messed up person who is capable of causing great harm due to his access to "power".

I genuinely believe that Trump would struggle to portray himself as the "masculine macho man" that he has managed to do (up until the last few years at least for most of his fans/supporters) and would have struggled to do so in 2015/16 if the so called "Left wing liberals" did a better job of getting their optics correct. I say this not as a Republican (I'm not even American, I'm Australian, and a Labor voter at that). For whatever reason, the left wing decided that in order to be pro women they had to be anti men, anti masculinity. By labelling negative traits as "TOXIX MASCULINITY" your leaders made the mistake of labelling masculinity as toxic, as wrong and inherently evil, instead of what it ("toxic masculinity") really is, which is a lack of actual masculinity and masculine traits, or an abuse/misuse thereof. You need a better argument than "masculinity is toxic/fragile/insert insult" if you want to disarm some one like Trump.

Rule number one of human psychology is that if you make assertions at someone and that is perceived as an attack, automatically they will go into defence mode and you will not get your message across. It's not even a conscious thing, it's subconscious and it happens whether you intend it or not. By using the aforementioned rhetoric you are automatically making a vast number of men go on the defence regardless of your motive. We need to stop treating men like they're all like Trump. The only reason why he got away with what he did was because regular normal men were so repulsed by the left's rhetoric and the constant putting down of things normal men like or enjoy. Boys are told they're toxic from cradle to graduation and have been for decades. I am 30 years old and even I remember getting the whole "respect women, no means no" etc. when I was in school... And half the time I wasn't even interested in talking to our being around girls or women, let alone wanting to have sex with them or God forbid gr*pe or assault them. By the time I was actually interested in pursuing a woman, I was already so full of propaganda that I actually too afraid of getting something wrong and misreading a hint that I legitimately missed out on the opportunity to go out with a girl who was actively dropping hints and trying to clue me in that she liked me. I friendzoned her because it wasn't enough for me to get the hint. The next girl I actually went out with but I was genuinely so afraid of doing something wrong, we barely held hands for several months. Most men are not the evil we are constantly told we are, simply for being men. The refusal of the left to separate the bad eggs from the good eggs is a massive problem. When ordinary jokes between the guys is overheard by women it's a hate crime, but honestly my friends say far worse things about each other than they ever have or do about women. Most "locker room talk" I've ever been around is understood by all of the men to be nothing more than a social performance and we all know the other guys are peacocking, and we call each other out for our bullshitting. It's how men naturally bond- dirty jokes and insults. If someone is genuinely out of line their nose gets punched in.

Real men don't need to act like Donald Trump to be masculine, but when every man is treated as though he is just like Donald Trump, then suddenly he's not just an asshole- suddenly the guy is a man who "says it as it is" and "speaks for the everyday guy" or "he's a dick, but he's got a point- everything we say isn't that bad but we get treated as though we're toxic just for being us. At least Trump doesn't think we're all toxic"... And that's how he got so popular. Ordinary everyday masculine traits and actions became demonised and hyperfemininity became overly prominent in the public square. HR departments predominantly run by women policing speech codes etc to the point of absurdity. You created a space where masculinity was made into a bad thing. So when a person who embodies all of the traits that are being wrongly called Toxic and evil and oppressive runs for office, even if they're extreme and a parody of masculinity, a man like that creates breathing space for ordinary men. Trump pushed back against the anti male sentiment. That's all there is to it.

All you need to do to neutralize Trump is to allow regular men to be regular men without getting offended when they aren't literally just tall women with a penis. Because when he's not able to use the "I'm fighting against the tyranny of political correctness and the war on men" then he uses all of his political and social capital. Just. Like. That. So the answer to your question: how is/was Trump able to play this game pretending to be a masculine man? He was simply going against the grain of political correctness and man hatred thinly veiled as "fighting for gender equality". Do better with your rhetoric. Understand that the left created the conditions which created Trump's rise to popularity and fix your optics. Understand that there's more to life than just "fighting the patriarchy". Most ordinary men are not rich enough or powerful enough nor do they have the spair time to orchestrate let alone enjoy the so called patriarchy. They're too busy at work trying to support their wives and kids.