A guilty plea from the Trump Organization's former chief financial officer in the criminal tax case against him would spell financial disaster for the family business, according to a former top federal prosecutor.

According to the New York Times, Allen Weisselberg, a top executive for the Trump Organization, is expected to plead guilty in a deal with the Manhattan District Attorney's office.

There are 15 felony counts against him and the Trump Organization. The charges stem from a "sweeping and audacious payment scheme" in which Weisselberg avoided paying taxes for up to 1.7 million of his income, according to prosecutors.

Weisselberg's deal would see him receive five months in prison, compared to a sentence of at least one year if he was found guilty.

Andrew Weissmann, a law professor at New York University, said on MSNBC's "The Last Word" that it was over for the Trump Organization once Allen Weisselberg pleaded guilty.

The company would be held responsible for the charges if crimes were committed by Weisselberg.

The trial for the Trump Organization is scheduled to take place in October. Weisselberg will face trial if he doesn't take a plea deal. He and the Trump Organization have denied the charges.

The consequences for the Trump Organization are huge because of the leverage that Donald Trump has.

This is a big deal for people who think Donald Trump did this for money.

If he were advising Trump on how to handle the investigations and lawsuits against him, Weissman said he would focus on the consequences of Weisselberg's plea deal.

There are at least six lawsuits, three criminal investigations, and a civil investigation against Trump. Mary Trump and Hillary Clinton have both been sued by him.