Joy Reid asked law professor Paul Butler if Trump's conduct regarding the Comey firing meets the legal threshold for obstruction of justice.
"As a prosecutor, I'm looking at a pattern of conduct," he said.
"Corruptly impede an official proceeding, corruptly means you know what you're doing was wrong. Well, you know what you're doing is wrong when you're meeting with the FBI director and you ask the vice president and the attorney general to leave the room so you can have a private conversation about 'Give my boy Mike Flynn a break.'
"You look at a pattern of conduct where again, you reach out to the intelligence directors to give Flynn a break and they say no, we can't call off the FBI. Then you go to the FBI director, he says no, I can't do that, I can't show you any loyalty, and then you fire that director. And then, Joy, after all of that, you know Flynn is under investigation. You give him a call. You say words to the effect of 'man, I know the feds are after you, but keep your head up.' The struggle is real. Give me a break," Butler said.
"I've seen obstruction of justice convictions on less evidence than this."
"Matthew Miller, you also have extraordinary information coming out of some of the officials to the recipients of overtures from Donald Trump," Reid said.
She recounted the recent story about Admiral Mike Rogers addressing the NSA staff. She said it was not just "unusual" for information like this to come out about a briefing, but that the agency briefing even took place.
"Rogers reportedly admitted that President Trump asked him to discredit the FBI and James Comey and stated there's no question that we, meaning NSA, have evidence of election involvement and questionable contacts with the Russians.
Miller said Jeff Sessions and Rod Rosenstein signed off on Jim Comey's firing.
"One of the questions we have to ask, will fall to Congress to ask, what conversations did they have with the president, what conversations did they have with other people in the White House. And if he was complaining to them about the way Comey was handling the investigation before he fired him, I think that's another piece of evidence that goes to his intent in making that decision," he said.
Richard Painter, former White House ethics counsel, responded to Reid that he would never have authorized a president to usher the attorney general out of the room so the president could have a private conversation with the FBI director investigating his campaign.
"Absolutely not," he said. "This is clear evidence of obstruction of justice."
"Now we hear that administration officials in the transition team were trying to establish secret communication, encrypted communications with the Russians. All I can say is, if President Obama's transition team tried that, President Bush's team would have made sure they got locked up, would have told the president-elect 'pick up your men in Guantanamo on January 20.
"This is treason," he said bluntly.
"It's a violation of federal law for people to be communicating encrypted messages, negotiating with the Russian government before the president takes office. I am amazed anyone on Capitol Hill is tolerating a combination of obstruction of justice, Russian espionage, collaboration with Russian espionage, now violations of the Logan Act. Very serious situation for this administration."
"It does beg the question, where are the resignations? Where is the outrage on Capitol Hill?"