We are right now perhaps the closest to a dictatorship the US has ever been.
Lincoln and FDR both wielded immense power (some of it used for good causes), so they would probably be the only cases comparable or more like a dictatorship than these early days of the 2nd Trump administration.
Congress and the Supreme Court are perhaps the two biggest obstacles to a dictatorship from the Executive Branch but only if they actually wield their power. But I think whether the other branches fight or not we're looking at the US becoming a semi-free country like Hungary under Orban. While dictatorships can happen here, I'm still pretty skeptical we're only a month away from an Enabling Act of 1933 (what Hitler used very early on as chancellor).
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