How much money could Donald Trump have to pay in fines if his businesses are penalized?

The investigation into potential mishandling of classified documents has dominated the headlines since the home of Donald Trump was raided earlier this month. On Friday the affidavit justifying the FBI search was made public, outlining the extent of Trump’s legal woes, but it is far from the only investigation into the former President.

The Trump Organization is the subject of two probes in New Year investigating business affairs dating back decades.

Earlier this month former Trump Organization chief financial officer Allen Weisselberg pleaded guilty to 15 criminal tax fraud charges. Weisselberg admitted to being involved in a series of schemes that allowed top Trump executives to avoid paying taxes. Manhattan DA Alvin Bragg said Trump’s eponymous firm is directly implicated in “a wide range of criminal activity.”

Simultaneously, New York Attorney General Letitia James is conducting a separate civil investigation into claims that Trumps business misrepresented the value of its properties to evade taxes and secure additional loans. Trump was recently questioned by state officials and reportedly invoked the Fifth Amendment 440 times in a single day.

What will Trump’s punishment be if his company are convicted in New York?

Over the years Trump has gained a reputation for wriggling out of financial investigations, but he is attempting to see off these latest threats while fighting numerous other lawsuits. Even if he is to avoid any personal convictions for his company’s business practices, Trump could be forced to foot the bill for some fairly hefty fines.

Yahoo! Finance consulted with a number of legal experts to gauge how severe the punishment could be for Trump, if prosecuted in New York.

Miriam Baer, a former Manhattan federal prosecutor, said that the financial penalties for the Trump Organization could be tough. She predicts that a conviction would lead to “a very severe fine” at the very least.

During Trump’s first impeachment trial Norm Eisen served as special counsel, and he can offer insight into the likely legal path for Trump in these New York Investigation.

“I’m anticipating very, very serious penalties,” said Eisen, floating the possibility of “corporate death penalty” if the Trump Organization is convicted of the more serious financial crimes. This could see his flagship business wound up, something that has happened to his business concerns in New York before.

The New York Attorney General’s office won a $2 million judgement against a Trump-controlled foundation and was involved in a $25 million decision against Trump University. Both of those organisations folded in the aftermath of those decisions.

Most crucially, while it is the Trump Organization that is under investigation, the former President will likely feel the consequences of any ruling that is handed down against it. Dan Alexander, a senior editor at Forbes and author of a book on Trump’s businesses, explains that Trump’s personal wealth will take the hit of any financial punishment.

“If there are penalties placed on the Trump Organization, this won’t be coming out of some other shareholder’s pocket or something like that,” says Alexander. “If they get fined $5 million or $20 million or $100 million, that will be directly subtracted from his personal net worth.”