The massive $350 million-plus judgment rendered against former President Donald Trump on Friday in the civil lawsuit brought by New York Attorney General Letitia James is a double whammy.

Paying such enormous damages seriously depletes the net worth of even a self-proclaimed billionaire. More devastating to Trump, the court’s decision eviscerates his public image as a shrewd New York real estate mogul — an image he has carefully cultivated for decades.

Yet the enormous damages are not the only blow to Trump’s pocketbook.

The massive financial headaches for Trump are just beginning. Before he can appeal the verdict, Trump will have to post a bond or pledge assets that could tally close to $400 million, equal to the verdict plus 9% post-judgment interest. This assures that if Trump loses the appeal, the state of New York will collect the money.

A business litigation observer previously told NBC News that Trump would have to pay a nonrefundable fee of $18 million to obtain a bond (for a $370 million judgment, so slightly more than the actual judgment). Any company putting up the bond will demand collateral.

If Trump needs to pledge any New York properties or assets to the bonding company to secure the appeal bond, an independent monitor appointed by Judge Arthur Engoron would have to be notified by Trump in advance.