This post has been updated.

Michael Cohen will be in court Monday — along with President Trump's lawyer and even porn star Stormy Daniels — as a judge weighs whether to halt the government's review of materials seized from Cohen's office and hotel room a week ago. Trump's team hopes the judge will let it sort through the documents first.

The apparent Hail Mary to assert attorney-client privilege is the first legal battleground of the post-raid Cohen saga, amid increasing indications that the president's lawyer/fixer could be in real trouble — and possibly even a pivotal figure in the Russia investigation, as we found out Friday.

But what are the big questions here? Below are a few.

1. What's in the documents/on the tapes?

The fact that Cohen has made tapes of his conversations has caused a fair amount of excitement among Trump's opponents and concern among Trump loyalists. Even aside from that, though, seizing documents via a raid — a raid of the U.S. president's lawyer, no less — is an extraordinary step that suggests prosecutors made a rather compelling case to obtain the warrant from a judge. It also suggests the information could be extremely important.

And the fact that both Cohen and the White House are trying so hard to prevent a team of prosecutors from being the first to review the documents suggests that they see something potentially unhelpful coming out of them.

Yes, this may be perfunctory. And yes, Trump's attacks on the raid may be driven more by politics than genuine fear. (A government raid of his lawyer would seem to bolster his argument that the “deep state” is coming after him guns-a-blazing.)

But if Cohen has been serving for more than a decade as Trump's “fixer” — as his own attorney recently acknowledged and as Cohen has proudly proclaimed, comparing himself to Ray Donovan — it stands to reason that those documents and tapes may detail plenty of problems Cohen has “fixed,” starting with Daniels. It's a Pandora's box.

2. Was Cohen acting as Trump's lawyer or fixer?

Which brings us to just how much attorney-client privilege pertains to these documents and tapes. It involves two things:

  • Do the documents describe Cohen's efforts to further criminal activity (in which attorney-client privilege is moot)?
  • Was Cohen even acting as Trump's lawyer, or instead as a fixer who just happened to have a law degree?

The first one has been a big question since the raid. But the latter could also be significant, because as the Atlantic's David A. Graham wrote last week, it could mean all kinds of communications that would otherwise be privileged could be opened up to investigators.

We already know Cohen said he didn't inform Trump about the Daniels payment, which experts say means he wasn't even acting as Trump's lawyer. “You can’t be providing legal advice and services if you are not acting as a lawyer, nor can you be providing attorney-client protected legal services to a client completely unaware of what you are doing,” former federal prosecutor Patrick Cotter told me last week.

If that's how other business was handled, it may mean that the attorney-client privilege Trump has said is “dead” never really existed in the first place.

Cohen's recent legal works appears to have been limited, with his lawyer saying in court Monday that Cohen had 10 clients in 2017 and 2018, but only three to whom he provided legal services: Trump, GOP donor Elliott Broidy (for whom we found out last week Cohen had negotiated a hush-money payment) and Fox News personality Sean Hannity. But Hannity doesn't even appear to have had an official attorney-client relationship.

3. Was there a slush fund?

This is the biggest unanswered questions when it comes to Trump's potential involvement in the Daniels case, because Trump declined to answer it. Here's the exchange from two weeks ago, when Trump for the first time denied knowledge of the payment:

Q: Mr. President, did you know about the $130,000 payment to Stormy Daniels?
TRUMP: No. No. What else?
Q: Then why did Michael Cohen make those if there was no truth to her allegations?
TRUMP: Well, you'll have to ask Michael Cohen. Michael is my attorney. And you'll have to ask Michael Cohen.
Q: Do you know where he got the money to make that payment?
TRUMP: No, I don't know. No.
Q: Did you ever set up a fund of money that he could draw from?

Plenty of folks have suggested there's no way Cohen made the Daniels payment without checking with Trump. I disagree. But I do think the likelihood that Cohen made the payment without Trump's knowledge and out of the goodness of his heart is much tougher to believe. And his statement on this — that he “facilitated” the payment — is conspicuously worded.

The Wall Street Journal has reported the Cohen groused to those around him about Trump not reimbursing him. And it seems at least theoretically possible there was some kind of a fund to deal with these issues without telling Trump — thereby maintaining Trump's plausible deniability. Until we have a firmer denial, it's a possibility.

4. Did Cohen make similar arrangements like the Stormy Daniels one?

This may seem redundant when it comes to No. 2, but the original question here was whether Cohen may have violated campaign finance law by paying Daniels $130,000 in hush money shortly before the 2016 election. And, as Philip Bump noted, determining whether it was aimed at the campaign may come down to whether Cohen made similar arrangements previously — when there wasn't a campaign.

Since then, we've found out that Cohen arranged a similar hush-money deal for prominent Trump donor Elliott Broidy during the 2016 election. And last week AP and the New Yorker reported on another deal between the National Enquirer's parent company and a doorman who alleged Trump had fathered an illegitimate child. Cohen acknowledged he knew about the situation, but he said it was only in his capacity as Trump's spokesman and that he wasn't involved in the payment.

All of these happened during the 2016 election campaign, and at least two of the three involved Cohen. If he never did this kind of thing before, it would be more difficult to believe it wasn't aimed at the election — and that it didn't amount to an illegal campaign contribution.

5. What happened in Prague?

This might actually have been the most interesting development of the weekend: a McClatchy report Friday night that investigators have determined Cohen was, in fact, in Prague in the summer of 2016.

Why is that significant? Because the Steele dossier — a private intelligence report compiled by former British spy Christopher Steele — included a claim that Cohen met with a Russian official in Prague to talk about Russia's interference and advocacy for Trump in the 2016 election. Cohen flatly denied that he had ever been to Prague.

If Cohen denied ever being in Prague and it turns out he was there, that would be perhaps the biggest example yet of an apparent coverup of contact with the Russians. And it would be pretty compelling evidence of possible collusion.

6. Would Cohen flip on Trump?

Underlying all of this, of course, is what bearing it has on Trump. The president's lawyer being charged and even convicted of crimes that did not involve Trump would be one thing. Matters would get a whole lot more serious if (a) Trump were implicated, or (b) Cohen flipped on Trump.

The Cohen case is being handled by the U.S. Attorney's Office for the Southern District of New York, which got its referral from the investigation led by special counsel Robert S. Mueller III. But that doesn't mean Cohen couldn't cut a deal that involved cooperating with Mueller. Former top Justice Department official Harry Litman told me last week that there was “nothing preventing” such a development and that it was “a likely prospect to consider.”

Cohen, though, has expressed complete loyalty to Trump. “I’d rather jump out of a building than turn on Donald Trump,” he told a radio station last week.

Things, of course, have a way of changing as circumstances change. And jail time has a way of compelling people to do things they would rather not.