My guess is that President Donald Trump has never read Machiavelli and therefore knows nothing about his political writings. If he did, he might recognize in Machiavelli some of his own previous good luck in politics.
Machiavelli thought politics was a 50/50 game: 50% of politics was historical knowledge, political calculation, strategy and charisma; the other 50% of politics was fortune or luck. To Machiavelli, the first 50% was a masculine sentiment; the second, feminine. And of the two, the second was the more important. All the planning and calculation in the world was no match for fortune or luck.
Calculation, knowledge and charisma are human characteristics that can be developed, but fortune and luck are impossible to develop or control. For Machiavelli, there were two approaches to fortune for a leader: one was to plan so bad fortune could be arrested; the other was to challenge fortune. Arresting fortune by planning is when you take that jog just before an important job interview and lock yourself out of your apartment. Having a hidden key arrests fortune.
Challenging fortune means you don’t play it safe — you run risks in life. And, finally, fortune and luck are most dangerous when you try to control and direct them. Asking Trump if he will leave office after losing presumes fortune will not be on his side. It is an attempt to control and direct fortune and may bring the opposite outcome — as when the same kind of question was put to Trump in 2016.