The recent fines leveled against former President Donald Trump in the New York civil fraud trial against him could be "sending exactly the wrong message," according to former federal prosecutor Andrew Weissmann. New York Attorney General Letitia James has sued Trump and his family for $250 million, accusing them of inflating Trump's net worth and the value of his assets to secure better deals and loans.

Trump and his family have dismissed the accusations and maintained their innocence, accusing prosecutors of being politically motivated. New York City Judge Arthur Engoron ruled last month that Trump, his sons, their businesses, and executives committed fraud. Engoron has issued a limited gag order against Trump in the case, barring him from making potentially threatening public statements about court staff. However, Trump has violated the order twice and has been fined $15,000 in total.

Former prosecutor Andrew Weissmann argues that the use of fines to punish Trump for violating the gag order could be ineffective, as Trump is not likely to be deterred by monetary consequences. Weissmann expressed concerns that Trump's continued defiance may lead to further legal trouble and damage to his brand. This case could potentially result in Trump losing some of his properties and being barred from doing business in New York. The court will continue to rule on other accusations in the coming weeks, including falsifying business records and insurance fraud.