But what started out as a threat to Donald Trump's business and personal wealth has now spiralled into political uncertainty.
One looming question now is how would Trump use this bill payment to mobilise his supporters ahead of the election.
This is what we know about the case against Trump and his battle to pay a big bill.
If he fails to pay the sum, Trump's bank accounts may be frozen and The Trump Organization's assets seized by the state.
Donald Trump has complained on Truth Social that finding the money to allow him to appeal has been "VERY EXPENSIVE".
New York Attorney-General Letitia James said winning the civil fraud case against Donald Trump was a "tremendous victory" for the state.
On Friday morning, Trump wrote on Truth Social that he had "ALMOST FIVE HUNDRED MILLION DOLLARS IN CASH". »