He gave the Prince the advice that would be the fastest road to disaster for his reign. It worked and the City eventually set up a Republic.
Machiavelli knew that a prince was not to be trusted and that they trusted no one. So he played on the prince's valid paranoia. His advice turned the Prince into an absolute rotter.
Same happens to anyone who takes Machiavelli's advice to the Prince seriously.
Machiavelli studied and wrote about the failed Roman republic looking for the flaws and commenting on successful methods hoping that future generation would take heed after suffering enough insufferable Princes.
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