MSNBC legal analyst Andrew Weissmann discussed what Trump might be in for when he has to sit down with his probation officer this Monday.

As we already discussed here, Trump has "a virtual meeting scheduled with a New York City probation officer from his home at Mar-a-Lago with his attorney Todd Blanche at his side after he was found guilty on all counts in the hush money trial against him last month."

As Weissmann made clear to host Jen Psaki, that meeting may include a whole lot of questions Trump doesn't want to have to answer:

PSAKI: I want to ask you about, and it was right before we came on the air, there was some exclusive reporting by NBC News that Trump is scheduled for a Zoom interview with the probation officer tomorrow. It's over Zoom, which I think isn't typical how it's done, although this is not a typical scenario.

How do you expect this to go and what are you watching for?

WEISSMANN: Yeah, so the manner is certainly not normal. Usually, it's in person, not by Zoom, but you can imagine because of Secret Service, et cetera, that accommodations have been made.

You know, this is one where Donald Trump really can, it's his to lose. You know, there's nothing wrong with his telling the probation office, I didn't do anything wrong and I'm not admitting guilt and I'm planning on appealing.

That's every defendant has a right to do that. But if he were to start saying the kinds of things that he has been saying during the trial and after the trial and attacking the jurors, the witnesses, the judge, family members to foment sort of an anti-law enforcement, a false anti-law enforcement sentiment, you know, that's not going to go that well, to say the least.

He'll also be asked a lot about his personal finances in terms of paying a fine. He'll be asked about his, whether he is associating with criminals, and it is sort of remarkable. It's just, it's the kind of thing that you just went down with your last guest, but, you know, he's going to have to sort of discuss whether he still coordinates with Roger Stone, Paul Manafort, Steve Bannon.

Remember, all of those people have been found guilty by a jury and are felons themselves. So that's another area where the probation department could ask questions and I'll be interested to see what Donald Trump has to say about that.

Sadly, as Psaki and Weissmann discussed, we may not find out what happened during the hearing unless someone leaks.

PSAKI: What he says. Now, when you say it could not go well, what could be the impact of this meeting? What will we hear after it's over?

WEISSMANN: Sure. Great. So this is a standard part of sentencing where the probation department has an, there's sort of an arm of the court and they give a private confidential report to the judge.

So we will not directly see it. We may hear about it through the parties, but this is a report that's given to the judge. Both sides should have access to it to challenge any statements there, but it's basically allowing the court to learn more information about a defendant.

Now in connection with Donald Trump, you may be saying, well, how much more, yeah, what could they possibly learn that you don't know? But yeah, but, you know, he has not been through this process, so this is part of what probation does with every defendant and most defendants are not that well known to, to the sentencing judge.

But here there are, as I mentioned, the areas about, for instances, associating with known felons is something that we have not heard about directly. We also, you know, I could imagine the judge, or at least probation, being interested in his statements with respect to jurors and witnesses and the judge and, you know, what, if anything, he's planning in doing in connection with, in that regard, what his statements are about acceptance for responsibility.

The judge needs to throw the book at him when we finally get to the sentencing hearing, but whether he does remains to be seen. I'd love to be a fly on the wall at this probation hearing since I don't expect it to go well for Trump.