"So I have heard from others that this is a – essentially a sort of crime that involves a paper trail. And paperwork or paper trail crimes are very easy to prove. So you are saying it’s going to be difficult but wouldn’t the bar be really low to prove that?" Lemon asked. 

"I disagree with that. I've heard that statement from, I think a mutual friend of ours. It’s easy to prove the paper crime if the person’s name is on the paper. Here the paper trail can show us exactly how this payment was made, exactly how Michael Cohen was reimbursed, and exactly how they booked it. What I'd be shocked if the paperwork showed is a direct link to Donald Trump. If there is an email, text, a memo where Donald Trump says ‘Yes guys, do it this way’ or 'I'd like you to do it this way,' that’s a smoking gun. But short of that, the paperwork is an important part of the story, but just saying it’s a paper case, there's a paper trail, doesn’t necessarily get you to the core issue of the defendant or the potential defendants’ criminal liability," Honig said. 

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Hostin, a former federal prosecutor and co-host of ABC's "The View," said something similar to what Lemon had suggested on Monday. 

"I think the severity matters a little less than how easy it’s going to prove. Many of the charges that they’re looking at are falsifying business records. We know he’s done that for a really long time," Hostin said. "His chief financial officer is in prison at Rikers, serving time for falsifying business records, so it wouldn’t be a difficult thing to prove and that’s a misdemeanor charge. Misdemeanor charges are criminal, and it’s about six months."

Later in the segment, Hostin said she believed Trump would be imprisoned. 

"I think he will be imprisoned this time. I’ve been saying it for two years but I really believe, four cases in four different jurisdictions and a lot are paper trail cases. Do you know how easy paper trail cases are to prove?"

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Alyssa Farah Griffin said she felt "uneasy" about the case because it "carries the shortest sentence."

Hostin repeated that it was "the easiest to prove."

While they didn't name Hostin in the discussion, Lemon and Hostin are old friends and were once CNN colleagues. Honig has also interacted warmly online with Hostin, like him a former prosecutor, and she wrote a gushing blurb for his book about former Attorney General William Barr.

Some Democrats fear that a potential charges against Trump could backfire. 

"This is an open-and-shut, books-and-records misdemeanor," Norm Eisen, attorney and senior Brookings fellow, said Monday. "Now, to elevate it to a felony is more complicated."

"[T]here are far more serious crimes for which he should also be held to account," David Pepper, a former chair of the Ohio Democratic Party, told Axios.

Fox News Digital's Anders Hagstrom contributed to this report.