There is no question in my mind that if trump had been president in 1941, there is no way the US would have entered WW2, which means that he would have sided either passively or actively with the Nazis. The evidence is overwhelming for this kind of pure speculation. Trump is nothing if not transparent. Whether it's his unprincipled haphazard transactional approach to negotiations, his knee-jerk predatory 'America First' reflex, or his blatant fondness for tyrants. He has no pretense to alliances based on common values. If trump can be said to believe in anything it’s the authority of the strongman, based on the notion that might (be it military, political or economic) makes right. I'd go so far as to say that his support for Hitler would have been active. He would have told Hitler, Europe is yours, North America ours. That trump would have sided with the Nazis should be disqualifying for any person with a shred of morality or human decency (especially so for any Jew).
If trump believes in anything, it's strength, because he is so profoundly psychologically weak, intellectually, emotionally, and character-wise. It's a major reason he cannot side with Zelensky, he perceives him as weak, and trump can never associate himself with perceived weakness. The basic impulse of a psychologically weak individual is to speak in grandiose terms, using hyperbolic, exaggerated language, and lying liberally to mask their weakness. They also need constant reassurance and validation, which in trump's case, comes from cheering campaign rally crowds and constant media attention. Weakness also leads to bullying those perceived to be weaker, which is why trump has focused on disrespecting and attacking Canada economically and rhetorically.
Most dangerously, psychological weakness drives a need to break things and destroy in order to demonstrate (to oneself as much as to others) strength. The strong, confident, courageous, skilled, experienced leader builds, while the weak, vulnerable, unskilled, incompetent leader destroys. Moreover, weakness leads to a compulsion toward vicariousness ie. associating with strength that you do not possess yourself. Again, this is a source of trump's attraction to Putin, Orban, Xi, Erdogan and Kim, and why he would have certainly sided with Mussolini and Hitler.
In addition to a compulsion to be destructive, inner weakness makes a leader easily manipulated. He is prone to flattery and compliments, which from a strongman is desperately craved and feels like validation, but from a perceived weaker party will provoke self-awareness and consequently self-loathing which leads to disdain. This means that getting what you want from trump starts with how you are perceived by him, which is easy to see since he is so transparent. Flattery works if you are stronger, resistance if you are weaker. This is why Justin Trudeau's fatal mistake was to run down to Mar-a-lago when summoned by trump. And why Mexico's Claudia Scheinbaum, who keeps a distance and stands up to him rhetorically, appears to be more successful dealing with trump.
Inner weakness like trump's means he will be entirely focused on satisfying immediate emotional needs, and incapable of achieving any goal that requires strategic thinking and long-term planning. When trump said he will solve the Ukraine War and Gaza in 24 hours, it was a reflection of this. Everything to trump needs to happen quickly, because he is not capable of sustained attention to complex matters. In any negotiation, time is always trump's enemy before he loses interest, and in the case of Ukraine, trump is certainly no match for Putin, and Putin knows it. Putin knows that trump needs his approval, and will side with him against Zelensky in every instance. All Putin needs to do is feed trump excuses for blaming Zelensky, which he will readily accept. In trump's mind the aggressor is never to blame because aggression indicates strength. Trump is not capable of pressuring Putin for fear of losing his approval. On the contrary, he will take at face value everything Putin tells him, to show Putin he's a member of the club. Putin will string him along, maybe throw trump the odd meaningless bone, which trump will trumpet as progress. It can never occur to trump that supporting Zelensky fully against Putin is actually the only way to get Putin's respect and force him to the table for good faith negotiations. In trump's mind Putin needs to win and Zelensky needs to capitulate, because every negotiation is zero-sum, there is a clear winner and a clear loser. For trump, Putin has all the cards, as he said. What Zelensky, should have said to trump when they met in the Oval Office was, "But you have cards too. Why are you so ready to fold them?"
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