Former Trump Organization executive weighs Trump's odds of avoiding indictment and jail

Prosecutors in New York are reportedly on the verge of deciding whether to file criminal charges against the Trump Organization and its chief financial officer, Allen Weisselberg. Lawyers for the Trump Organization and former President Donald Trump have a Monday deadline to convince Manhattan District Attorney Cyrus Vance Jr. not to file charges, The Washington Post reported Sunday.

On CNN Sunday evening, Jim Acosta asked former Trump Organization executive vice president Barbara Res what she thinks will happen this week. "Based on what you know about how the Trump Organization works, do you think that Donald Trump himself is in legal jeopardy here?" he asked.

Res, who has written a book criticizing her former boss, said she isn't sure what kind of case the New York prosecutors have against the loose conglomeration or business entities that is the Trump Organization, but nothing happens at the Trump Organization that Trump himself "doesn't know about, nothing major, so he is in this with, you know, both legs, and I think that if they get something it will be to go after Trump."

Subscribe to The Week

Escape your echo chamber. Get the facts behind the news, plus analysis from multiple perspectives.

SUBSCRIBE & SAVE

Sign up for The Week's Free Newsletters

From our morning news briefing to a weekly Good News Newsletter, get the best of The Week delivered directly to your inbox.

From our morning news briefing to a weekly Good News Newsletter, get the best of The Week delivered directly to your inbox.

Sign up

Res said Weisselberg "is definitely the key guy" and she's "surprised" he hasn't cooperated. "Trump has something on him, I would imagine — it's the only thing I can think of," she said, but prosecutors may well have gotten enough evidence on both Trump and Weisselberg from Weisselberg's deputy, Trump Organization controller Jeff McConney. Acosta asked if Trump "deserves" to go to jail, and Res said yes, "I imagine he does."

On Jimmy Kimmel Live last Thursday, Trump's former fixer Michael Cohen said the former president will "fight like the dog that he is," but Trump, Weisselberg, and chief operating officer Matthew Calamari are "all in trouble" because "there's documentary evidence that's in their possession." Prosecutors "don't really need Weisselberg or Calamari," he added. "One of them will flip to save themselves, and once you get Calamari, you don't need Weisselberg; when you get Weisselberg, you don't need Calamari. But the truth is they don't need either of them, because they have the documents to prove exactly the illegalities done by Trump."

"Look, it's just one giant family of grift, and there's not one of them that has a redeeming value to them," Cohen said. "If Trump goes to jail, will Melania wait for him?" Kimmel asked. "I don't think she's waiting for him right now," Cohen deadpanned.