An MSNBC panel on the future of former New York City mayor Rudy Giuliani, who is facing multiple investigations into his business dealings and his work for President Donald Trump, led a former prosecutor to speculate whether the former U.S. Attorney wants to find himself locked up with hardened criminals he once put away.

Speaking with host Stephanie Ruhle, former homicide prosecutor Glenn Kirschner said Giuliani likely has much to divulge about Trump — including going back to when he was New York City’s mayor and Trump was still just a developer — to SDNY prosecutors to avoid jail himself.

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Addressing Giuliani’s involvement in the Ukraine “quid pro quo” scandal that is engulfing the Trump administration, Kirschner said that and Rudy’s longtime relationship with Trump could yield a wealth of information to investigators.

“This is a conspiracy to defraud the United States by having a foreign country interfere in the upcoming presidential election,” Kirschner began. “Look. right now SDNY’s fiercely independent prosecutor’s office is engaged in a wide-ranging criminal investigation into Rudy Giuliani. I am hard-pressed to believe that they are not finding enough evidence to charge Rudy Giuliani. Then the question becomes: what does Rudy do? Does he flip on the president?”

“I was really interested to see that now somewhat infamous comment by Giuliani that if he [Trump] tries to throw me under the bus, I have insurance,” he continued. “Let’s think: he was a U.S. Attorney in New York. He was mayor in New York for a combined 13 years. how much information could he have about dirt that Trump did in New York?”

“I don’t know,” host Ruhle protested. “You seem pretty excited about that but wouldn’t you think Michael Cohen would have a whole lot of incriminating evidence against the president and Michael is sitting in jail and the president is at Mar-a-Lago?”

“Do you think Rudy wants to sit in federal prison like Michael Cohen is with all those people he put there when he was U.S. Attorney?” the prosecutor persisted. “That’s not a hospitable environment for Rudy Giuliani. ”

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