On Wednesday night, legal and political nerds stayed up late waiting for the Justice Department to drop its midnight brief responding to Trump’s request for a Special Master, which he urges is needed to sort out any privileged material that might have been seized by the FBI during its search of Mar-a-Lago.

Attorney General Merrick Garland has said repeatedly that the Department intended to speak through its court papers only, and this filing did not disappoint.

It’s worth noting first that every time that Trump has amplified this case, it has gotten worse for him.

For starters, the search might have gone wholly unnoticed had Trump not posted about it publicly. Garland responded with a firm and clear two minute news conference that made clear that he personally authorized the search and meant business.

Then Trump made noise about the alleged lack of transparency and demanded that the affidavit supporting the warrant be unsealed, even while his legal team stood on the sidelines and let Judicial Watch and the media argue the case to the judge.

When a heavily redacted affidavit was unsealed, it made headlines because of the sheer volume and nature of the documents at issue: a thousand pages of sensitive documents, including those marked with the highest level of top secret classification, putting Trump and the GOP on the defensive.

Now, in response to his demand for a special master, the Department once again has revealed some truly damaging evidence in its late night filing.

Let’s walk through some highlights.

Lordy, There Are Photos

The most headline-grabbing aspect of the Department’s filing was the inclusion of photos taken during the search. The most damning was included as the final document in an attachment.

It includes some folders marked in red font as Top Secret // SCI (meaning secure compartmented information) and Secret // SCI.

Department of Justice

If you look carefully, you can see further classifications including HSC (Human Intelligence Source classified) and other clear indications on the folders that these do not belong anywhere outside of a secure, locked down facility, let alone in the residence of a private citizen.

According to forensic journalist Scott Stedman, for example, the marking “TK” refers to “Talent Keyhole” meaning secret intelligence from spy satellites and planes.

Department of Justice

These images might explain why Trump’s immediate reaction to the search was that the FBI was planting evidence.

There simply isn’t another explanation for what these documents were doing there, other than the obvious one that Trump took them and kept them for himself in violation of the Espionage Act and other laws.

Moreover, the Department made clear in its filings that it has video security footage of documents being moved in and out of the storage room where boxes of them were kept, as well as numerous civilian witnesses with whom it had been working to establish probable cause to search for evidence of the crimes.

The “it was all planted!” story is thus unlikely to fly before a jury, nor with the broader court of public opinion.

The photo provided by the Justice Department is giving security experts heart palpitations, by the way.

These types of documents can normally only be seen by a select few people with the highest levels of clearance, and only within a secured facility that is guarded round the clock. These are the nation’s most valuable pieces of intelligence, and to see them handled like this is horrifying to those familiar with normal security protocols.

It’s the Obstruction, Stupid

Setting aside the physical evidence amassed showing apparent violations of laws like the Espionage Act and misappropriation of government records, Trump’s other problem is that this is becoming a fairly straightforward case of obstruction.

In its filing, the Justice Department revealed more key information about the history of its efforts to recover these highly sensitive government documents from Trump. Again, it looks very bad for the former President.

First, a quick review of early efforts to recover documents.

After the National Archives tried for over a year to recover missing boxes of documents that Trump took with him to Mar-a-Lago, he finally returned 15 boxes of them. Inside were some top secret, highly classified documents.

Alarmed, NARA referred the matter to the FBI, and a grand jury was convened to investigate. From there, a subpoena issued on May 11, 2022 for any remaining documents.

Ostensibly to comply with the subpoena, the parties arranged to have a team of DOJ lawyers, including the head of the Counterintelligence section, head to Mar-a-Lago on June 3, 2022, where they met with Trump’s lawyers and briefly with Trump.

None of these facts has ever been disputed by Trump or his legal team.

Moreover, as the Associated Press reported, the question of why Trump held onto documents remains unanswered.

The Justice Department filing offered little new insight, noting simply as follows:

"Counsel for the former President offered no explanation as to why boxes of government records, including 38 documents with classification markings, remained at the Premises nearly five months after the production of the Fifteen Boxes and nearly one-and-a-half years after the end of the Administration."

What happened next was really damning.

According to the filing, Trump’s team presented FBI agents with 38 additional documents with classified markings, including 17 labeled top secret. These were provided inside a redwell that was double-taped.

However, one of Mr. Trump’s lawyers present during the visit “explicitly prohibited government personnel from opening or looking inside any of the boxes that remained in the storage room, giving no opportunity for the government to confirm that no documents with classification markings remained.”

Instead, a lawyer named Christina Bobb signed a sworn statement, importantly attesting that she had been provided information and was authorized by Trump’s office, to certify as to the return of all documents.

Here is what she swore, according to the Department’s filing:

"Based upon the information that has been provided to me, I am authorized to certify, on behalf of the Office of Donald J. Trump, the following:"

"a. A diligent search was conducted of the boxes that were moved from the White House to Florida;"

"b. This search was conducted after receipt of the subpoena, in order to locate any and all documents that are responsive to the subpoena;"

"c. Any and all responsive documents accompany this certification; and"

"d. No copy, written notation, or reproduction of any kind was retained as to any responsive document."

We now know that the statement that “any and all responsive documents accompany this certification” was wildly untrue. We can conclude this for two simple reasons.

First, the FBI reviewed security footage and spoke to civilian witnesses familiar with the matter and determined that more documents existed.

The Department wrote:

"Through further investigation, the FBI uncovered multiple sources of evidence indicating that the response to the May 11 grand jury subpoena was incomplete and that classified documents remained at the Premises, notwithstanding the sworn certification made to the government on June 3…"

"The government also developed evidence that government records were likely concealed and removed from the Storage Room and that efforts were likely taken to obstruct the government’s investigation."

Second, we know this because the FBI went and actually retrieved many more documents in its search of the premises.

The search turned up three classified documents from desks inside Trump’s office. And from his residence, they retrieved more than 100 documents inside containers marked with classification warnings, including top secret restricted ones.

The Department rather drily noted:

"That the FBI, in a matter of hours, recovered twice as many documents with classification markings as the 'diligent search' that the former President’s counsel and other representatives had weeks to perform calls into serious question the representations made in the June 3 certification and casts doubt on the extent of cooperation in this matter."

The FBI also took (and returned) three passports held by Trump. As commentator Prof. Joyce Alene observed, the passports were found in a desk drawer that also contained classified material, something that had the effect of “rather neatly linking the former President to that material” and making it harder for Trump to argue that he was not personally handling the documents.

After all, it’s one thing to deny you knew about random top secret documents in boxes in a storage room, and quite another to deny you knew about the ones you kept with your passports in your office desk drawer.

In any event, in a post on Truth Social complaining about the photo of top secret documents on the floor of his office, Trump admitted that the documents were originally in a “container” in his office before the FBI laid them out on the ground. Trump may not understand that this is a straight out admission that he knew the documents were there.

Three other things to note here on obstruction.

First, obstruction under 18 U.S.C. Sec. 1519 carries a hefty penalty of up to 20 years. That will give prosecutors significant leverage in the case. That penalty is higher than the penalties per instance of the other crimes being investigated and, importantly, could more easily apply to others in Trump’s orbit.

Second, those in his orbit involved in the “diligent search” (the one that wound up being a complete sham) could themselves be charged with obstruction, meaning there are good opportunities to flip witnesses.

After all, who gave Trump attorney Christina Bobb the critical information that all documents had been returned and that there were no responsive documents remaining, if not Trump or his attorney Evan Corcoran?

And will Corcoran really take the fall for a guy who just hired him? This is actually now a clear conflict of interest for Trump’s own attorneys, since they may have to testify against their client, and they should resign from the case in light of it. (They likely won’t, but really they should.)

Third, an obstruction case can be prosecuted without the concern that a jury might have to see highly sensitive, classified documents that might be needed to prove an espionage case, which is a real logistical nightmare and itself presents a question of national security.

One final note. There are real and increasingly painful political consequences to Trump’s continued legal battles over the search of Mar-a-Lago.

His motions and missives will continue to place the matter front and center in important races in the remaining ten weeks leading up to the midterms. The question of whether GOP House and Senate candidates will stand with their presumptive party leader or condemn his actions creates yet another powerful wedge that could diminish enthusiasm among Republicans while firing up Democrats.

It could also continue to shift persuadable voters against the GOP.

The GOP was already on the back foot on abortion rights. Now, the apparent theft of top secrets by Trump, followed by a clumsy obstruction caught on tape and witnessed in real time by civilians now cooperating with the Department of Justice, could cause the GOP to stumble as it fights to retake Congress in November.

If the take by Ohio Republican Representative Jim Jordan of the House Judiciary Committee is any indication, Republicans may have real trouble finding the right approach. After viewing the damning FBI photo, yet somehow ignoring the fact that Top Secret // SCI documents were right next to a TIME Magazine cover kept by Trump as a memento, the official House Judiciary GOP tweeted:

“That TIME Magazine cover was a huge threat to national security. 🙄”

One can almost picture from this blind loyalty to Trump how Rep. Jordan managed to ignore crimes committed right in front of him for years while a coach at Ohio State University.