Like Watergate, But Stupider

Some of us are old enough to remember the name Rose Mary Woods. She was the fiercely loyal secretary to President Nixon who claimed she had, on her own, accidentally erased five minutes out of a total 18½ minute gap on an audio tape back in June of 1972. To do this, she would have had to simultaneously press audio controls that were several feet apart.

This was, in a word, a stretch. In fact, it became known as the “Rose Mary Stretch” from those that doubted the truth of her testimony.

Fast forward 50 years to June 2022. In a superseding indictment that dropped yesterday in the federal case against Trump in Miami, a property manager for Trump named Carlos De Oliveira stands accused of conspiring with the ex-president to delete a server that contained security camera footage—evidence that the Justice Department had demanded in a subpoena three days earlier.

Specifically, De Oliveira, who was added as a defendant in the superseding indictment, told a Trump employee in the “audio closet” that “the boss” wanted the server deleted. When the employee responded that he did not know how to do that and that he did not believe he had the rights to do that, De Oliveira asked, “what are we going to do?”

So that sounds like a pretty damning case of obstruction that got added. But wait, there’s more! Remember that infamous Bedminster meeting in July 2021, when Trump pulled out a top secret, classified plan to attack Iran and waved it in front of a group of random people, remarking about how it was still classified and, since he was no longer president, he couldn’t declassify it? That’s now charged as well specifically.

Let’s take a closer look at the superseding indictment and walk through its three most important aspects: 1) The added obstruction charges, 2) the addition of De Oliveira as a defendant, and 3) the new count under the Espionage Act related to the classified Iranian war plan. Bottom line: It all adds up to considerable new legal jeopardy for the former president.

Stupider Watergate

When the government issues you a subpoena for video tape surveillance, and you instead decide to destroy it rather than turn it over, that’s a crime. Well, duh.

The “well, duh” matters here, because no matter how Trump tries to smokescreen his way through the complicated question of classified documents (“I didn’t pack them! The FBI planted them! Anyway they were all declassified by my big brain!”), the jury intuitively will understand what was going on when Trump tried to destroy evidence. That move shows what lawyers call “consciousness of guilt”—and why they always say the cover-up is often worse than the crime.

Trump is now charged with two additional obstruction crimes: attempting to “alter, destroy, mutilate, or conceal evidence” and inducing someone else to do so. These charges carry hefty maximum prison sentences of 20 years. If convicted, Trump wouldn’t get the maximum, since he’s a first time offender, but it would very likely mean some prison time.

The specifics of what went on are laid out in the superseding indictment, but this section is worth highlighting because of someone referred to as Trump Employee 4. (This is from the annotated NYT discussion, which is why it’s in light orange and numbered “28.”)

It’s fairly clear that Trump Employee 4 has already spoken with prosecutors and given them this critical information. We should expect that there is grand jury testimony from Employee 4 as well.

So what would turn this into more than a “he said/he said” case? For starters, there is a very interesting chronology of events. Check this out:

In other words, the day after receiving the draft subpoena, Trump decides he needs to talk to his property manager for 24 minutes. What did they talk about?

There are some clues. The next day, on June 24, Trump also lets co-defendant Walt Nauta know that he needs to speak to him. Nauta, who was supposed to travel with Trump to Illinois on the 25th, changes his travel schedule so he can fly to Palm Beach. He even texts someone that day saying he would not be going to Illinois with Trump. This part kills me. Shushing emojis? Really? 🫢 🤫

Then there was this series of exchanges involving that same Trump Employee 4 who undoubtedly has testified before the grand jury and is cooperating with prosecutors.

So, some obvious questions here. Why would Nauta cancel his plans, lie to his friend about why he was canceling and shush him from asking more, then communicate with both De Oliveira and Trump Employee 4 about needing him for something?

Why, indeed. The next day, on June 25, 2022, Nauta travels from Bedminster to Mar-a-Lago. De Oliveira tells a colleague (Trump Employee 5) that Nauta is coming down, but asks that employee “not to tell anyone” because Nauta “wanted the trip to remain secret.” De Oliveira also tells Employee 5 that Nauta wanted De Oliveira to find out from Employee 4 “how long camera footage was stored.”

Hey, that’s not suspicious at all, right? A long phone call with Trump, canceled plans, then a secretive meeting about camera footage? Perfectly normal stuff.

Later on June 25, De Oliveira and Nauta meet up in person and go to the security guard booth where surveillance video is displayed on monitors, then walk with a flashlight through tunnels where the Storage Room was located, observing and pointing out cameras.

Again, normal, everyday stuff.

On Monday the 27th, De Oliveira heads to the IT office and asks Trump Employee 4 to step away so they could talk. They walk through the tunnels to the audio closet near the White and Gold Ballroom, and that’s where De Oliveira makes his ask that the server be deleted.

Like I said, like Watergate but stupider.

A few things to note before we move to De Oliveira as a new defendant. It isn’t alleged in the superseding indictment that De Oliveira actually succeeded in having the server destroyed or that any evidence was actually lost. But that doesn’t matter for purposes of the statute, because an attempt to do so is treated the same as actually doing so. 

Trump’s statements on Truth Social, unsurprisingly, may come back to bite him. On July 10, 2023, he posted that he had “QUICKLY PROVIDED SECURITY TAPES FROM MAR-a-LAGO on the BOXES HOAX,” but now he seems to have left out the part about instructing his employees to delete the server.

Finally, CNN earlier had reported that an employee at Mar-a-Lago was responsible for causing a flood of the server room where surveillance video was kept. That flood resulted from having (checks notes) drained the hotel pool into the room. It now seems that the employee responsible was De Oliveira. That incident raised suspicions around De Oliveira, but it’s not clear that it actually damaged any evidence, nor did the timing (last October) coincide with the subpoena from late June.

Carlos De Oliveira, Defendant 3

Now that De Oliveira is part of the cast of this show, it’s worthwhile gaming out what role he might play. Both he and Nauta have critical information about what Trump asked them to do. Both are looking at serious prison sentences, and so both are possible candidates for the prosecution to flip.

De Oliveira is particularly vulnerable. As legal expert Harry Litman stated on MSNBC, “De Oliveira is just tailor-made to be a cooperating witness. He has everything to lose.” He made a series of false statements to investigators and he made a series of moves that show he attempted to destroy evidence. For whatever reason—perhaps a misplaced loyalty to Trump, fear of reprisals, or pressure from his Trump-paid attorney—De Oliveira has not cooperated so far. 

But the clock is ticking, and he had better get out ahead of his co-conspirator Nauta on a deal to cooperate. Any deal gets a lot less attractive if someone else flips first.

Former prosecutor Joyce Vance, in that same MSNBC segment, stated she believes De Oliveira has almost “no choice but to flip” because he’s looking at 20 year maximum charges, which will result in a big chunk of time in prison. She notes that agents visited De Oliveira in his home, and told him he was free to end the interview at any time, 

but he proceeds to lie to them in a bald-faced manner about when the boxes and the items from Washington first come down to Mar-a-Lago. They have him dead to center if he does not cooperate. 

And what do they get if he does cooperate? He is putting Trump front and center in this scheme to obstruct. They have Trump wanting to figure out if the videos can be erased…that he in fact knew that what he was doing was wrong.

Even if De Oliveira holds out, his statements to Trump Employee 4 could come into evidence, because they fall under “admissions against interest” by a party defendant. And it’s hard to imagine that De Oliveira would make such a demand on his own rather than at the request of “the boss.”

It will be fascinating to see how far De Oliveira and Nauta go to protect Trump. Now that De Oliveira knows what evidence the government has on him, he may be reconsidering his non-cooperation—especially if it seems Trump is going to be found guilty anyway.

Waving the Report

Prosecutors love a good story to tell the jury that gives a glimpse into the motive of a defendant, even if that isn’t directly relevant to the underlying charges. The story that jumps out of the Mar-a-Lago indictment takes place in July 2021 at another golf resort, Trump’s Bedminster club in New Jersey.

According to press accounts and the indictment itself, Trump held a meeting with writers for his former chief of staff Mark Meadows, who were working on his biography. During that meeting, which was recorded at Trump’s request to ensure accuracy of his account, Trump pulled out a top secret military plan to attack Iran, allegedly drafted by Gen. Mark Milley. Here’s what the indictment says about that moment, from the NYT annotated version:

The odd thing about the first indictment was that, while the top secret war document was discussed, the accompanying charge against Trump for having illegally retained that document was not included.

That changed on Thursday. The indictment now includes a specific charge under the Espionage Act under Count 32.

Perhaps the reason that it wasn’t originally charged is that the document was not among those found and seized at Mar-a-Lago under the search warrant. Rather, it apparently was among the classified documents returned to the National Archives in January 2022, when Trump’s legal team returned some 15 boxes of documents. 

The inclusion of a charge for illegal retention of the Iran war plan is significant for a few reasons.

First, as former prosecutor Andrew Weissmann noted, this means that the audio tape from the meeting in July of 2021 at Bedminster, along with accompanying testimony from witnesses, is likely admissible now because it is directly relevant to a charged, illegally retained document.

Second, the document itself can also likely come into evidence, albeit under strict rules around who can view it, in order to buttress the case, perhaps from eyewitness testimony, that this was in fact the document they saw Trump wave around, brag about, and admit was still classified. That will make his defense that he declassified everything in his possession a lot weaker.

Third, this in turn will help show Trump was lying in public statements, for example those made during an interview with Fox’s Bret Baier, in which Trump claimed, “There was no document.” If this was in fact the document, and others saw it, and it was classified as he admits on that tape, that erodes his credibility even further, to the extent that is even possible these days.

Irony is dead

I would be remiss, and failing to honor the spirit of Schadenfriday, to not point out that Trump now stands credibly accused of attempting to delete a server. This, after all, is what he spent all of 2016 accusing Hillary Clinton of having her staff do, as if it were the worst crime imaginable. He even said during the debates that she should be prosecuted by a Special Counsel for it.

And if that isn’t karma coming back to bite him hard, I don’t know what is.