“The Trump Organization, which is neither organized nor a big business organization, always struck me as an oxymoron,” half-jokes Tim O’Brien, a senior columnist at Bloomberg, to Molly Jong-Fast, host of The New Abnormal.

But with the announcement from New York Attorney General Letitia James that she’s joining forces with Manhattan District Attorney Cy Vance on a criminal investigation into the organization, name semantics is the least of the leadership’s problems.

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“They’re all going to start to have to figure out ‘Is it worth it to continue to throw our lot in with Donald or to find our own lawyers and protect ourselves,” says O’Brien. “A prison term is a pretty ugly outcome, and money doesn’t really keep people from avoiding that.”

Seriously, though, Molly wants to know: Could Trump go to jail? Well, yes and no, as O’Brien explains in the latest episode of The New Abnormal.

However, it’s not just Trump on their radar—Allen Weisselberg seems to be as well. “If Weisselberg knows everything he’s been there for since the mid-’70s and if he flips and has records and evidence and tape recordings, anything like that, that shows Trump had knowledge of anything these people think is criminal, it will get tricky for Trump,” O’Brien says.

Then, senior politics editor Matt Fuller comes back on the show and reveals how painfully clear it is that the GOP has no idea how to talk about Jan. 6, and Daily Beast gender reporter Emily Shugerman breaks down Texas’ latest abortion ban, which includes suing people who help the women who get them.

Plus! Andy Levy joins as co-host for the episode and talks about how little McCarthy cares about poor kids, why Andrew Giuliani is the most pointless failson of all the failsons (even Don Jr.), and whether Matthew McConaughey could stand a chance against “heartless embryo” Gov. Greg Abbott.

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