Many have made up their mind already. It is an intellectually dead debate.
The answer lies not in thinking about Trump but the constitution.
Democracy is lazily defined as a mixed constitution, one in which the leader (government) is moderate, the people are reasonable and calm, and the wealthy care for others. This ideal is presented by the historian Polybius (200-118 BC) and was endorsed in the Federalist Papers (1788), a central document of the Founding Fathers of the United States. However, Polybius was a Greek hostage in the service of a leading Roman family. His personal wellbeing depended on the moderation of his owners.
Plato (428-348 BC) condemns oligarchy and tyranny as degenerate forms of governance. In his Republic (ca. 375 BC) he makes a striking parallel between society and the individual. He claims that the faults of the individual mirror those of society and vice versa. For him, an oligarch is a person who is part of a small group which controls power. As such they are not money-minded, since they can obtain what they wish without exchanging something for money. A tyrant emerges from a wealthy class that rebels against democracy.
Trump operates within a democratic society. Let us see in Plato’s Republic what he thinks happens in the last phase of democracy (557a) before the arrival of the tyrannical man and tyranny:
citizens are free and have freedom of speech (557b)
society becomes drunk with freedom (562c)
children no longer listen to their parents (562e)
teachers fear students (563a)
the young disregard the old (563a)
confusion between debt and loan (563b)
confusion between men and women (563b)
people behave like animals (563c)
disregard for laws both written and unwritten (563d)
Plato concludes this analysis by indicating that ‘extreme freedom seems to be nothing other than extreme slavery’.
ἡ γὰρ ἄγαν ἐλευθερία ἔοικεν οὐκ εἰς ἄλλο τι ἢ εἰς ἄγαν δουλείαν μεταβάλλειν καὶ ἰδιώτῃ καὶ πόλει (564a3-4).
The tyrant emerges from the ruins of democracy. He appears as a doctor with a cure for society or a lawgiver or an expert beekeeper (for whom the bees are the rest of society) (564bc). For Plato, a degenerate democracy will be replaced by an innovative tyranny. In his analysis the rise of the tyrannical man is due to the collapse of democratic society.
Freedom versus stability.
Classical Athenian democracy was aware of the fragility of its society at the end of the 5th century BC. For this reason, a law was passed providing that anyone could legally kill those who conspired against the democratic constitution (410 BC). Such a provision is usually enacted when it is too late.
According to Plato’s interpretation, those who are criticizing politicians such as Trump, believe that democracy is in a downward spiral of degeneration. They think that he has a chance to become a tyrant because democracy has failed.
Has democracy really failed?
On November 11th, 1947, Churchill told Parliament: "No one pretends that democracy is perfect or all-wise. Indeed, it has been said that democracy is the worst form of government except for all those other forms that have been tried from time to time."