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Transcript: The Beat with Ari Melber, 6/29/21

Guests: Chai Komanduri, Robert Ray, Jennifer Weisselberg, Rebecca Roiphe, John Flannery

Summary

Reports emerge that charges in the Trump Organization criminal probe are imminent. The former daughter-in-law of Allen Weisselberg, Jennifer Weisselberg, discusses the Trump Organization criminal probe. Are there any true moderates left in the Republican Senate Caucus? Former independent counsel Robert Ray discusses the Trump Organization probe.

Transcript

NICOLLE WALLACE, MSNBC HOST: THE BEAT WITH ARI MELBER starts right now.

Hi, Ari.

ARI MELBER, MSNBC HOST: Hi, Nicolle. Thank you so much.

Welcome to THE BEAT. I`m Ari Melber.

And we are tracking reports the charges in the Trump Organization criminal probe are imminent, which would mark the first criminal charges of an ex- president`s company ever, stoking fear in Trump world, intrigue across New York, questions in the national Republican Party, and many, many expectations.

(BEGIN VIDEO CLIP)

HALLIE JACKSON, MSNBC HOST: Right now, this morning, the Trump Organization and people who`ve worked for it on high alert as we speak.

WALLACE: Criminal charges for the Trump Org could come down any moment now.

RACHEL MADDOW, HOST, "THE RACHEL MADDOW SHOW": Trump`s lawyers met with prosecutors to try to talk them out of filing criminal charges against the Trump Organization. That apparently did not work.

ERIN BURNETT, CNN: Prosecutors also expected to charge chief financial officer Allen Weisselberg.

UNIDENTIFIED FEMALE: If those charges are filed, those would not be the only charges.

(END VIDEO CLIP)

MELBER: As mentioned there, the financial architect of Trump Org could be charged, Allen Weisselberg, who has clearly not been cooperating, according to sources.

And he might face indictments for evading taxes and compensation, provided the tuition, apartments and leases. The Trump team admits these charges are coming, which means this story has turned from an if even a few weeks ago to a when.

And we`re now past this deadline that prosecutors set that Rachel was referring to there for any final arguments or appeals by Trump lawyers. And while grand juries are secret, we now know a bit about that final round of high-stakes clashes because Trump`s lawyers argued to prosecutors the indictment would hurt the company`s relationship with banks and lenders, that it would be unfair to employees.

After the meeting, Trump lawyers spoke out, one of them saying that, after 50 years of practice, they have never seen a DA`s office target a company over employee compensation or fringe benefits.

And yet here we are. Think about it. There`s no suggestion in this very serious story of legal heat, no suggestion even from Trump`s own lawyers right now that those arguments they made reversed the DA`s plan to indict.

Now, as a matter of legal history and precedent, there are independent experts who do say that building an entire criminal case on those taxes for benefits would be rare, experts telling "The Wall Street Journal" that.

Another saying they couldn`t recall any cases based on that theory alone, noting charges over benefits were typically part of larger cases, when prosecutors did bring them.

Now, that skepticism, it could prove relevant. Remember, after years of pursuing Donald Trump`s taxes all the way up to the Supreme Court and winning, the New York DA got them. If his only indictment is ultimately about other people`s benefits and not Donald Trump, well, while that matters, it may look legally narrow.

It`s also possible there are just other things coming that we don`t know about in this or in a later set of charges. The last time Donald Trump was trying to outrun a grand jury pursuing a lot of his people, a lot of whom got indicted, it was overseen by Bob Mueller.

And that one started pretty small too, indicting unknown aides, but it ended with much larger fish. The future of this case may depend on what Weisselberg does under pressure and whether Trump`s company and namesake itself is ultimately charged.

I want to bring in our experts, former federal prosecutor John Flannery, and Rebecca -- and just John Flannery, I should say.

(LAUGHTER)

MELBER: Good to have you here, John.

JOHN FLANNERY, FORMER FEDERAL PROSECUTOR: Good to be here.

MELBER: This is one that has passed the legal point of no return.

FLANNERY: Right.

MELBER: I say legal because, in life, anything can happen. There could be a pandemic or another one. So other things can happen.

FLANNERY: Right.

MELBER: But they did that final meeting. They did that huddle. There`s no evidence it reversed course.

If you were walking viewers through why this matters and what to expect, what do you see likely in these coming days?

FLANNERY: Well, I think that the meeting you referred to was really to see if Trump was going to offer a plea, rather than he was going to persuade them out of the case. Now, I wasn`t in the room, so I don`t know. But that`s more likely what was going on.

And it`s a polite way to put it to say, tell us what`s wrong with our case?

At this point, we`re in a position where we`re receiving information this is not just going to be against the corporation, it`s going to involve Weisselberg, and there was one report, and others.

So, we will see. And a nice question is, this a RICO prosecution, so, that we`re talking about a organized criminal entity? Now, if we want to study what impact this has on Trump, if he`s the ultimate target, just hypothetically, for the sake of argument, then what have they done?

They have attacked the one thing that concerns him more than anything else in the world, his money. He fought tooth and nail not to have his finance discovered. And when we had the Mueller report, it didn`t go there. It didn`t come close to Trump. It didn`t come close to his family.

But this charge against the corporation, still unformed for us to comment on, involves all of those things. It involves Trump by association with his closest friend, I assume, for all these years, Weisselberg, who is keeping his mouth shut, and it involves his company and those employees.

So what I`d say is, we have a dramatic opening, presuming there`s more to come. And until we see the indictment and know if it`s RICO and who else may be named and who is identified as Mr. X or Mr. Y, we don`t have the full import of it. But it`s hard to believe they spent all this time getting all those tax records and analyzing this and careful containers, so that nothing could be compromised, that this is just going to be a yawn.

So I think this is a substantial step, assuming we move forward from this point.

MELBER: Yes. Yes.

Counselor, stay with me.

I also want to bring in Rebecca Roiphe, who worked as an assistant district attorney in this very New York DA`s office.

Welcome.

What do you see coming next, based on your knowledge of these kinds of cases?

REBECCA ROIPHE, FORMER MANHATTAN ASSISTANT DISTRICT ATTORNEY: So I think this is a little unusual to have one indictment come out, and then potentially the more significant indictment come out later on.

But this isn`t a typical case. And I think, also, as you said about the experts saying that this is not -- we have never seen cases on just these fringe benefits, I actually think that this is different, in part because this is the gatekeeper. I mean, this is the person who was supposed to be watching and making sure that everybody in the corporation, in the organization is abiding by the rules, himself breaking the rules.

So, if you`re doing a broader investigation, and you come across this kind of tax violation, that`s a big deal. And people keep saying it`s not such a big deal, but tax violations are serious. I mean, somebody`s paying those taxes, and that`s the rest of us New Yorkers.

So, even though it`s not a major crime compared to the other ones that we know have -- or have been at least publicly reported to be investigated, it is significant. And whatever remains to come, I think these might be this the most readily provable crimes, and there may be others that the office is still investigating through this grand jury.

MELBER: Right.

And, Rebecca, you make the point that so much has focused on Allen Weisselberg as a person of intrigue and his relationship with Donald Trump, you make the point that, in any organization, a valid, honest one would have a CFO that is setting the financial standards, not finding loopholes that may or may not be criminal.

Take a listen to what the head of the Trump Organization had to say about all this.

(BEGIN AUDIO CLIP)

DONALD TRUMP, FORMER PRESIDENT OF THE UNITED STATES: Well, I call it the continuation of the greatest and most disgusting witch-hunt of all time.

And, look, there`s never been anything like it from the day I came down the escalator.

(END AUDIO CLIP)

FLANNERY: Well, I think we have our witch.

MELBER: Rebecca, where does the founder -- there you go.

Well, Rebecca, where does the founder fit into all this? Because the view of these Trump lawyers is, the whole thing would not be a case but for the name on the building.

ROIPHE: Right.

This refrain has been working well for the president from back when we -- you were covering the Mueller report. It has served him well in the public eye. The question is, how well will it serve him continuing on? And that`s part of the reason why it may be that they`re coming out with these readily provable crimes, because it`s harder to say it`s a witch-hunt when there are actual crimes that there`s no wiggle room, there`s no -- there`s -- it`s very hard.

I mean, of course, there will be a defense, but it`s very hard to defend against this crime, if it`s clear-cut through the documentary evidence. So, in some ways, that cuts against this kind of core theory on the part of the defense and the president that this is a witch-hunt.

That said, in another way, it sort of plays into it, because they can say, oh, come on. If this were anybody else, they wouldn`t pursue this tiny little fringe benefit crime. They`re only doing it because of my name and my political party.

And that is -- that`s working for them. And, here, the defense attorney should play that up because it`s good for his client. But how long it will work remains to be seen.

MELBER: John?

FLANNERY: Well, I was thinking that`s true. I think that is what the defense argument will be.

But the other this turns around is that this is Trump`s bank account. He reaches into his pocket and he takes out whatever he needs. That`s going to end.

And the banks that are going to give him the credit that he needs for the next crazy deal he has that he can`t cover because he`s in a hole financially as it is right now, that`s going to matter.

And what was the argument on Monday that`s come to us through the press about what they talked about? You can`t do this to the corporation. You know how this is going to harm us. This is really going to harm us.

Well, if that isn`t a pathway to attack. And often the criticism among us defense attorneys is that a prosecutor takes away the means to defend oneself by compromising the income that they have. And what better way to do it than to turn that organization into what it`s always been, a criminal organization, to stamp it as such, declare it as such, and then to move forward presumably with the rest of the cases?

MELBER: Rebecca, is this all a prelude to the DA trying to get Weisselberg to flip? And what happens if he doesn`t?

ROIPHE: So, I think it`s a little bit hard to read what`s going on right now.

I think that`s probably the best bet, is that they`re doing this because they have increased pressure on Weisselberg. And he`s been reluctant to cooperate, and perhaps this will change his mind.

Now, again, it`s -- this is not a huge felony. It is a felony, but it`s not a felony that you would face a major amount of jail time, perhaps not even any jail time. And given that, I`m not sure how successful this step will be in forcing him to cooperate.

But this may be a multistep procedure in which this is one of those steps, making him face the reality that is coming down the road. So that is entirely possible. There might be other reasons for doing this. It`s a little bit hard to tell. Perhaps there are statute of limitations. Who knows?

But I think the number one guess is, you`re right, they`re just trying to get Weisselberg to flip, so that they can actually get the head of this organization, instead of the second in command.

FLANNERY: I think there parts to this.

MELBER: And we have only about a minute left, but there`s another -- John, I want to get you on another story of your former SDNY veteran Giuliani facing the loss of his law license and facing an inquiry now into whether he lobbied for Turkey.

This is new, Giuliani fielding questions about whether he was acting for Turkey when he pushed the administration, in a strange bid to drop money- laundering charges against a particular gold trader. The inquiry, which had not been previously reported, according to Bloomberg, is not criminal, which is distinct from the Ukraine probe, which resulted in the FBI seizing all of those phones.

What does this mean, if anything, for Giuliani?

FLANNERY: Well, are we saying that he was also registered on behalf of the Turkish entity he was representing? Because that`s -- that implicates, to me, criminal problems for him.

Also, in addition, what was his authority to do this, and in contravention of what I believe was our national policy at the time? And it didn`t succeed, I think, because of that, if I remember some of the facts that were written about this.

Finally, it`s Rudy being rogue Rudy, doing whatever he wants to get a buck.

MELBER: Yes, I think that`s fair, fairly put, given that this was a time where he had a lot of access, and he would have what most people would consider a lot of money.

And yet, whether it was greed or rogue or a sense of impunity, he seemed to have his hands in a lot of different legal places.

My thanks to Rebecca and John for kicking us off.

John, we have a very special guest later in the program, and you are going to be a part of that segment. So, stick around.

FLANNERY: I will.

MELBER: Coming up, I have a interview later tonight with a key witness who has been turning over documents in this Trump DA investigation. Jennifer Weisselberg is here.

Plus, former President Obama with a warning about Republicans.

But, first, we have a very special take that may explain the future of the Biden agenda.

Stay with us.

(COMMERCIAL BREAK)

MELBER: You may have missed it amidst criminal investigations and heat waves and all kinds of other news, but President Biden calmly reached a jobs and infrastructure deal with a bipartisan group of senators.

Now Mitch McConnell`s trying to derail it. We know why. McConnell admits he wants to stop anything a Democratic president does. That`s 100 percent of his focus for Biden, just like for Obama. But McConnell claims his concern is the debt, which he has been supersizing under Trump.

(BEGIN VIDEO CLIP)

SEN. MITCH MCCONNELL (R-KY): Look, we now have a debt the size of our economy. I don`t know how many times I need to repeat this. We`re playing Russian roulette with the American economy.

(END VIDEO CLIP)

MELBER: The size of the debt, of course, largely applied for the last four years.

Now, there are real policy priorities at stake here, McConnell trying to strip this proposed deal`s investments in care for children, the elderly, and some action on climate change.

McConnell has brought the Republican Party around to his views, uniting them to oppose everything, just about, from floor votes on election reform, to the once traditional idea that, after a national security attack, like the insurrection, you have a commission to investigate it.

But for all the talk about a 50/50 Senate or the segments you have probably seen on Joe Manchin and the Democrats trying to hold every last member of their team together, can I ask you a question tonight? Do you ever noticed we don`t hear much about that same dynamic for McConnell?

Why is that? We don`t hear about him trying to bargain with a Republican version of Joe Manchin. And this matters, because it was not always this way. On close votes, the GOP Senate used to include its own mavericks, like John McCain, who dramatically destroyed Trump`s effort to gut Obamacare and broke with his party on money in politics and climate science.

(BEGIN VIDEO CLIP)

SEN. JOHN MCCAIN (R-AZ): The overwhelming body of scientific opinion in America and the world believes that human activity is causing climate change in the world.

(END VIDEO CLIP)

MELBER: Now, there are some structural differences too. When you`re in the majority, you need those 50 votes.

But McConnell`s using these obstruction tactics where he really only usually needs 41, unless, of course, that rule changes.

So, there is that. But it`s also true there were more moderate Republicans. Like, in the also partisan Bush era, there were Republicans like Senator Chafee, who broke with his party over big issues.

(BEGIN VIDEO CLIP)

FMR. SEN. LINCOLN CHAFEE (R-RI): I oppose the constitutional ban on states -- states allowing gay marriage. Principles of a just war.

QUESTION: Do you think our actions in Iraq and Afghanistan meet those criteria?

CHAFEE: Certainly not Iraq.

(END VIDEO CLIP)

MELBER: Chafee eventually left the GOP. He would argue the GOP left him.

And former Obama campaign aide Chai Komanduri notes that`s where the ideology meets the structural dynamics, because the Republican Party has limited districts where a moderate Republican can win.

And independent political scientist Norm Ornstein writes: "The data shows polarization is asymmetric, and conservatives are worse."

So for all the attention personalities, McConnell, McCarthy, the ex-blogger in Florida, there`s also a broader shift in the Republican Party and its membership across the board, missing moderates.

What does that mean for the country? What does it mean for the decisions that Biden has to make, even when he thinks he has a bipartisan deal?

We`re going to dig into the question for the Biden agenda after our shortest break in the hour. We`re back in just 60 seconds.

(COMMERCIAL BREAK)

MELBER: Welcome back.

We have been looking at vanishing moderates.

And we have our deep dive political conversation right now, which is always a special day here on THE BEAT. It is known as "Chai Day."

And we are joined now by political strategist Chai Komanduri, who worked on the Obama presidential campaign and has advised other Democratic campaigns.

Thanks for being here.

CHAI KOMANDURI, DEMOCRATIC STRATEGIST: Thank you for having me, Ari.

MELBER: As I sometimes mention in these segments, we`re indebted to you for some of the research we just ran through.

Why is it important to understand that, even if there weren`t a ton of Republican moderates in the old days, there`s a big difference between a few and virtually none?

KOMANDURI: Well, you can see the difference right now in this what I would say is so-called bipartisan infrastructure deal.

What we actually really have is a Republican deal that some Democrats or really Democrats in general support. But there`s nothing in this infrastructure deal that Trump himself wouldn`t have signed. The only reason he didn`t sign such a deal is because he and the Republicans were simply too lazy to put together a piece of legislation like this and send it to him for his signature.

Now, Biden and the Democrats did the work, and they, therefore, have this bipartisan deal. That seems to be the new definition of bipartisanship. Democrats do the work, and maybe Republicans, some Republicans, go along with it.

However, the old-fashioned version of bipartisanship was that Republicans would in many cases acknowledge and acquiesce on some level to the ideological priorities of Democrats. That simply did not occur here, which is why we`re so much -- we`re talking about this partisan budget reconciliation to get some of those priorities actually through.

MELBER: Yes, you lay it out. It`s very important, what you`re saying, Chai, because, sometimes, language has a way of having sort of residual associations.

KOMANDURI: Right.

MELBER: So, when people say, go negotiate or bargain, those meetings are thought of as automatically ending with something in the middle. And there`s a certain school of politics that likes that.

Or Joe Manchin, as you pointed out in one of our earlier discussions, he associates the filibuster as a tool for compromise. One can debate when that was true. It`s certainly not true now. So, the residual language there is that, no, it`s not a moderating device. It`s not a compromising device. It`s a Mitch McConnell hostage-taking device.

And it`s not personal. What I appreciate about your analysis is, this isn`t the personalities. This is the structure of what they`re doing. To that end, Mitch McConnell was asked a somewhat clever question about his favorite Democratic president. Guess who it is? Take a look.

(BEGIN VIDEO CLIP)

QUESTION: You`re stranded on a desert island and you can only have one companion. Your choices are Joe Biden, Barack Obama, Bill Clinton, or Jimmy Carter? Who do you choose?

MCCONNELL: That`s a tough choice.

(LAUGHTER)

MCCONNELL: Well, I wouldn`t choose Jimmy Carter. (OFF-MIKE)

Yes, I would pick Biden.

(END VIDEO CLIP)

MELBER: He lands on Biden, and yet he`s here to crush Biden`s agenda.

KOMANDURI: Yes, and it`s all very much by design.

I mean, we talked about last week how the Voting Rights Act would have been a long-term institutional investment in the future of the Republican Party. You most certainly would have increased the number of moderate Republicans who exist, because those moderate Republicans would have to exist, because market forces would force Republicans to go after young voters, more diverse voters, and then play in non-gerrymandered nonpartisan districts.

That would have increased the number of moderate Republicans. However, Mitch McConnell doesn`t want more moderate Republicans. He doesn`t like the moderate Republicans. And as much as he claims to dislike Trump, boy, does he love the Trump Republicans.

The reality is, the Trump Republicans are pliant, and they follow orders. To put it in a movie terms, they may roar like the T-Rex in "Jurassic Park," but what they really are is that cowardly lawyer in the outhouse, ready to be food for the real monster, who is Mitch McConnell.

MELBER: Always strong.

You mentioned the gerrymandering. I did want to get this data in there. You have FiveThirtyEight. They just crunched the numbers. They`re non partisan, but they note the Republicans hold about half the seats. But they represent just 43 percent of United States. It`s not just the Senate or just the Electoral College, as we have covered.

The House and state legislators -- legislatures are also tilted.

So, James Baldwin said not everything that is faced can be changed, but nothing can be changed that isn`t faced.

How much of your diagnosis here is about Joe Biden and every other Democrat understanding this reality to change it that way? And how much of it is about actually changing the underlying structures? I mean, if and when you had less gerrymandering, you might have broader participation, which, as you said in the long term, might be good for both parties or civic engagement as well.

KOMANDURI: Well, I think, to was credit, I do think Joe Biden actually understands this problem.

Michael Kinsley said a gaffe is when somebody accidentally says the truth in Washington. And when Joe Biden talked about how he did want a budget reconciliation that got through elderly care, childcare, some of these other priorities, that was widely seen as, oh, this is a gaffe.

But it was actually the truth. The only way Democrats were going to get their priorities through was through a partisan budget reconciliation process.

However, I do think that one of the major problems in D.C. is, there`s this sense that we have to, on one hand, unite the country and restore norms. But, on the other hand, we do have to sort of do things like the Voting Rights Act that would ostensibly help Democrats.

I think the problem is, is that we`re framing it incorrectly. The Voting Rights Act actually wouldn`t help Democrats. It would help moderate Republicans. It would help Republicans to be in nonpartisan districts in the long term.

What it would not help is MAGA Republicans. And I think that`s where the country and D.C. is very much still divided. Should we take the steps necessary to keep another Trump from rising? And the problem is that all the things that brought Trump to power are still very much in place.

And, in fact, in some cases, they`re stronger than ever.

MELBER: Yes, incisive, and, at times, low-key depressing. Chai Komanduri, there it is.

Thanks for coming back, sir.

KOMANDURI: Thank you.

MELBER: Appreciate it.

We have a lot more in the hour, including former President Obama taking on the MAGA rioters.

And a key witness in the Trump Org case. We like to go to the source. Jennifer Weisselberg is here tonight.

But, first, a very special guest on where the Trump Org charges are headed. That`s next.

(COMMERCIAL BREAK)

MELBER: All signs show to imminent charges against people at the Trump Organization, while Trump`s lawyers have been downplaying the idea that it`s serious if the case turns on the benefits issue we have been reporting, one lawyer saying it`s all to get back at Donald Trump anyway and the charges are much ado about nothing.

The charges that have been hinted at, though, like tax evasion or even fraud, can be important.

And we`re joined now for a special look at this with a special expert. We`re going to have -- we`re going to have federal prosecutor John Flannery back with us, but, soon, the special guest that I have promised.

He is a veteran lawyer who succeeded Ken Starr in one of the biggest legal roles in the nation and also represented then President Trump at an impeachment trial.

(BEGIN VIDEO CLIP)

TOM BROKAW, NBC SPECIAL CORRESPONDENT: You can now call Kenneth Starr the former independent counsel. His replacement was sworn in today.

The new man is Robert Ray, a star deputy for the past six months.

BRIAN WILLIAMS, MSNBC HOST: The House voted to impeach Donald Trump one month ago. The trial is now three days away.

Tonight, we learned the makeup of Trump`s defense team. It`s back to the Clinton impeachment with former independent counsel Ken Starr and his successor, Robert Ray.

ROBERT RAY, FORMER INDEPENDENT COUNSEL: The articles of impeachment, therefore, should be rejected, and the president must be acquitted.

(END VIDEO CLIP)

MELBER: I`m joined now by that very attorney, Robert Ray.

Sir, you are what they call a big gun in Republican legal circles. Thanks for being here.

RAY: Nice to be with you, as always, Ari.

MELBER: I`m curious what you think, based at least on the public information we have. How strong does the case look to you against Mr. Weisselberg and possibly against the Trump Organization or part of it?

RAY: Well, proceeding against the Trump Organization, of course, takes the benefit of the collective corporate knowledge doctrine.

You may be unable, for example, to prove in a criminal case culpable criminal conduct against any individual, but, collectively, if the company handed out fringe benefits that were not de minimis to individuals in the form of disguised wages or compensation, you have to pay payroll taxes on that.

And, from Allen Weisselberg`s perspective, if he received, for example, free rent in the Trump Tower, that`s income, which has to be reported on his income tax returns, including his New York state income tax returns.

So I assume that those are the -- sort of the outline of the charges that at least prosecutors in the DA`s office initially have in mind. Now, whether there`s more or not, I guess, is open to speculation.

But I wouldn`t characterize those benefits as de minimis fringe benefits. I mean, I have to think that rent in the Trump Tower, for example, is on the order of magnitude of multiples of $10,000 a month times 12 in a calendar year. That`s not an incidental or de minimis fringe benefits.

It`s not like tickets to a ball game. That`s a substantial amount of income. Well, it may not be substantial to a billionaire, but, nevertheless, to tax authorities, that`s a substantial amount of money. And if you didn`t pay tax on it, that`s a problem.

MELBER: So, if Weisselberg did that, you think that`s a strong criminal case against him?

RAY: Yes, I mean, I -- I don`t -- there`s usually not much defense. You sign your own tax -- your personal income tax return.

If you received a benefit, I don`t think you have a fair argument, well, I didn`t know that I was supposed to pay tax on it. Again, it`s not like a small benefit, fringe benefit. That`s a substantial fringe benefit that any accountant advising him, or he did his own tax returns, would tell him is something that you have to report as income.

MELBER: Very interesting coming from you.

And then, when you look at trying to make the wider case against part or all of the Trump Organization, some of his current lawyers are saying, well, that`s just targeting him politically. We showed some of the reporting about whether that`s a very common theory or not.

Do you think that`s fair game?

RAY: It is to some degree. I mean, taking on a corporation with regard to something like that, which is, let`s say -- if it`s limited to just failure to pay payroll taxes on fringe benefits, I think you could make an argument that taxing authorities, their primary interest is in seeing that those taxes are paid with presumably interest and penalties.

It is not usually the case that those are the kinds of situations that result in criminal prosecution. I can`t say it`s never been done. But that would be unusual. And so, if that`s the case, and you`re talking about the exercise of discretion, I think it`s fair game to argue what the motivation is.

I`m not saying that it`s any less serious or any less of a problem. But it`s certainly something that, if that`s all they have, and that`s the ticket that prosecutors want to punch, my guess is, they`re going to be met with a substantial argument by defense lawyers on the other side that it`s cherry-picking and it`s singling out for prosecution something that ordinarily is not prosecuted.

Doesn`t change the fact that taxes are still do and owing, but those are not the kinds of cases that are typically brought for criminal prosecution.

Individual is a whole `nother story. It`s also more difficult to prove than it is against a company. Again, taking advantage of collective corporate knowledge, the company is responsible for knowing that these things are paid.

Whether any one individual knows that there was an obligation to do so, and that fringe benefits were in fact paid, and that it was knowingly -- income was withheld and taxes, payroll taxes were not paid on those benefits, to try to do that against any single individual, including the former president, I think would be very difficult to do, which is one of the reasons why, in this area, you tend to see cases against the company, the corporate entity, rather than individuals.

MELBER: Right. Right.

And you`re reminding viewers of something we have been covering here, which is why prosecutors sometimes do like to go after that corporate angle.

Then there`s the wider history. You were involved, as mentioned, in the impeachment probe, which overlapped with certain issues, but was distinct, of course, from the Mueller grand jury.

But I want to put up on the screen just a refresher, because some of the Trump folks are saying, well, if this is all there is, they argue it`s nothing. This also could be the beginning. I mean, that case started with Papadopoulos being indicted in July 2017. Easy to forget that it wasn`t until October that you had Manafort and Gates, and that was 2017.

And it wasn`t until 2019, near more the end of the charging period of that probe, that you got to Roger Stone.

Do you see, based on the knowledge we have, any kind of long-term calendar here, where these supposedly imminent charges would be step one, and there would be later charges? Or do you think it`s different and unlikely here? What`s your view?

RAY: Look, it could be the tip of the spear. I don`t discount the possibility that the Trump Organization and individuals within the Trump Organization should be concerned, as I am sure they are.

What goes for public consumption, of course, is a whole `nother question. But the runway here is with the Cy Vance through the end of this calendar year, while he`s still holds office. I think he aims to come to a conclusion, that is to say, a prosecutorial conclusion, before he leaves office. And this may be all there is, but I wouldn`t discount the possibility that there may be more.

And, of course, prosecution is a moving target. The prosecution of Allen Weisselberg, if that`s what`s coming, obviously, I think, is being done in order to apply pressure to him to see if there can -- what the prospects are for obtaining additional evidence that can be used against one or more other people.

And you don`t know what those efforts will bring, and you`re not going to know that until the DA`s office actually pulls the trigger and initiates the prosecution, which I guess is what we`re speculating about now.

MELBER: Yes.

RAY: But trying to figure out what this means over the next several weeks or months is anybody`s guess. But there`s a lot more runway here.

MELBER: Yes.

RAY: And so I think it`s certainly a possibility that there will be other charges, sure.

MELBER: Yes, really fascinating, especially given your background. We have had you before. I hope you will come back.

Robert Ray, thank you, sir.

RAY: Nice to be with you.

MELBER: Absolutely.

And, as promised, now we turn to another expert, a former federal prosecutor, John Flannery.

John, these are times where many things are debated. Viewers may remember Mr. Ray from his service in the impeachment.

FLANNERY: Right.

MELBER: Pretty striking to hear him tonight live on air say that Allen Weisselberg has a big criminal problem.

FLANNERY: Well, I thought it was interesting.

I don`t know which theory they`re going within the indictment, the theory that he mentioned, which I don`t see any problem with, which is that you put it on Weisselberg, and he fails to report certain things he should report.

But if you emphasize it from the corporate standpoint, if there are more people than Barry Weisselberg who were the beneficiaries of these funds that were not declared, either by Barry or deducted from the income of the employee by Weisselberg at the Trump Organization, so if there were a number of people who were receiving benefits, and, on the corporate books, they were not deducting from the fees that -- from the salaries they got these funds that they were getting for benefits, then you have a twofer.

You have the person who had the benefit didn`t declare it, and you have the corporation.

MELBER: Yes.

FLANNERY: So, if you have a series of events by the corporation...

(CROSSTALK)

MELBER: But I`m going to direct you a little.

I`m only going to direct you because I`m curious, in terms of lawyering.

FLANNERY: Yes.

MELBER: What do you think of the fact that one of Donald Trump`s most loyal visible impeachment lawyers, who also, as I mentioned, Republican successor to Ken Starr, doesn`t seem to be throwing any cold water, at least on the Weisselberg case?

FLANNERY: No, he does not.

And I was prepared if he stopped there to say, it`s so good that Robert and I could agree on this.

MELBER: Well, you are. Tonight, you`re agreeing. I remember it`s not so many years ago you would disagree.

FLANNERY: Yes.

MELBER: Do you think that speaks to the strength or the straightforward nature of that case?

FLANNERY: I think it speaks to the fact that it seems impossible to deny what happened here.

The benefits are large. He conceded that. They are more than one instance. They go on for years. And so it`s very hard to say it`s de minimis, one of those Latin terms, it`s not very big, it`s very small, and we should give a stiff speech and let the person go. Not here.

And...

MELBER: Tell us exactly what de minimis means.

FLANNERY: De minimis means a tip of 5 cents as compared to $7,000.

(LAUGHTER)

FLANNERY: So, if I`m giving you tickets to a game, it costs more than a few cents, but if I`m giving you a luxury apartment at Trump`s tower, and it costs $20,000 a month...

MELBER: Right.

FLANNERY: ... and I let you do it for two or three years, then we`re talking about some real serious money.

And the man on the street can`t do that.

MELBER: Or, John, if you`re a CFO at this company, and you make -- allegedly, you make say 200K, and then you`re getting another 100 or 200 or 300 more K in other value, well, that seems like it`s a part of your compensation that the federal government and tax authorities might be defrauded by.

FLANNERY: Right.

And 50K for your kid`s annual grammar school charges. That`s what Barry got. So, yes, that`s a lot. And what it says is, it`s the arrogance, because who would even think they could get away with that? About somebody who is arrogant, saw themselves above the law, and would do this.

And that is the correct prosecutorial discretion to go after a person like that, or a corporation that operates in that fashion, because they`re all these other corporations that are trying to figure out how to make things done, how to raise the morale of their people, and so forth.

And this is what Trump does. Trump has a respect for no one, nor anybody around him. And so he -- and money is right at the top of the list, and that`s why I think it`s so poetic that he`s on the wrong side of this charge that his organization is his best friend and financial consultant.

MELBER: Yes.

Well, John Flannery on more than one topic tonight, we appreciate your legal expertise, as always.

FLANNERY: Thank you.

MELBER: That was certainly interesting, at least on our side of the ledger here, we thought.

I`m going to fit in a break, but later tonight, former President Obama speaking out about the Capitol riot. We have that for you.

And, after all this talk about Allen Weisselberg and what`s going on over there and the lawyers, well, we`re going to get to a fact witness, his former daughter-in-law. Will he flip? Next.

(COMMERCIAL BREAK)

MELBER: In court, lawyers are fine, but witnesses are way more important.

And we turn to a key witness in the probe we have been covering, a former family member for the man at the center of this crimes probe.

Jennifer Weisselberg is Trump Org CFO Allen Weisselberg`s former daughter- in-law. She`s met with prosecutors in this very case several times, turning over boxes of documents. She has said she expected charges from the start.

And now, with those charges imminent and Weisselberg himself facing the possibility of jail time, she joins us on THE BEAT.

Joining me now is Jennifer Weisselberg.

Thank you for being here.

JENNIFER WEISSELBERG, FORMER DAUGHTER-IN-LAW OF ALLEN WEISSELBERG: Thank you for having me, Ari.

MELBER: It`s a rapidly escalating case.

A couple of quick questions before we get into depth. When is the last time you spoke to investigators?

WEISSELBERG: A week ago Friday.

MELBER: What was the topics they were most interested in?

WEISSELBERG: It has to do with the things that are going on in the grand jury now.

But the specifics of the content, the specific questions and who was asking them and who they refer to, it`s really important that they remain confidential, because we want to win this case.

MELBER: The DA who you`re speaking with, the investigators have asked you not to reveal the nature of your conversations with them?

WEISSELBERG: Correct.

MELBER: Let`s then look at what we`re learning publicly, not just drawing on whatever private information you have given them.

But what we`re seeing is the outlines of multiple reports of an indictment against Mr. Weisselberg. And both sides seem to agree that one goal would be to get him to flip and cooperate.

He has reportedly completely resisted that. Do you think that could change?

WEISSELBERG: I absolutely do think that can change. I do think it can change, yes.

I was wrong to think that he would flip. But now that I think about it, it makes perfect sense to me, Ari, because he lives in a bubble, where Donald promises him everything, and everything he has ever promised him has been true.

And I do believe that he is not resourcing his own attorneys. I do believe that they`re paid by Trump, and that he`s been promised things by Donald in the family in order to make sure that him and his family are taken care of.

But the X-factor for me -- and this is something the DA and I are continuing to discuss with my attorney -- is that there are things that Allen is not aware of. He can try to control all he wants inside the organization by going to work every day, but there are things that he does not know about.

There are things that might surprise him about his own child. There -- he is blind to the fact that he believes everything that Donald promises him and everything his sons are telling him.

And I have the proof to back up the fact that that`s just not true. And I have been able to lead the investigators to the right people. And those people, I have learned, have been walking the grand jury through the evidence.

So my documents have become paramount to the investigation. And my fight, as a mother, to get a fair settlement in my divorce or post-judgment divorce was just to take care of my children. That meant that I knew that you -- it`s almost like cost of living, which is what the forensic had said.

You can`t pretend to be going to private school, you can`t pretend to be having a Range Rover, you can`t pretend to be living in the city, when you`re making $3,600 every two weeks. It doesn`t add up.

MELBER: Jennifer Weisselberg, a witness in this case, thank you for us.

WEISSELBERG: Thanks, Ari.

MELBER: We will be keeping an eye on what all the witnesses have to say.

We`re going to fit in a break.

When we come back, Obama on the election lies and insurrection.

(COMMERCIAL BREAK)

MELBER: Tomorrow, the House will vote on Speaker Pelosi`s plan to create a select committee to investigate the Capitol insurrection.

It is a swift way to break through Republican obstruction in the Senate, where there was the Republican effort to completely block any vote on whether to even have a riot commission.

Former President Obama speaking out about all this and his concerns about the election lies.

(BEGIN VIDEO CLIP)

BARACK OBAMA, FORMER PRESIDENT OF THE UNITED STATES: The guardrails I thought were in place around many of our democratic institutions really depend on the two parties agreeing to those ground rules, those guardrails, and that one of them right now doesn`t seem as committed.

(END VIDEO CLIP)

MELBER: A diplomatic way to say one party attacking the guardrails.

We will have, of course, coverage of that House vote tomorrow.

We also want to bring you an update on the tragic condo collapse in Florida.

An engineer had warned in 2018 evidence of major structural damage there. Residents were told, however, the building was -- quote -- "not in bad shape." Photos show significant corrosion in the basement. This was two days before the horrific collapse. Twelve residents confirmed dead, 149 people missing.

President Biden will visit that site on Thursday.

We will continue to update on what we learn about what happened there.

That does it for this episode of THE BEAT. Thank you, as always, for watching.

"THE REIDOUT WITH JOY REID" starts right now.