Rudy Giuliani Appears to be Claiming Privilege Over Hundreds of Items He Already Agreed Were Not

Based on statements that Rudy Giuliani and his attorney Robert Costello have made in the Ruby Freeman suit, he should be claiming privilege over no more than 43 items total.

He is claiming privilege over around 400.

We can say that based on two claims, made in sworn declarations.

First, Rudy submitted this declaration stating that all his comms from the coup conspiracy would be in the materials archived by TrustPoint as part of the SDNY search of his devices.

Mind you, there’s a claim in that declaration that Costello’s declaration debunks — and it explains a lot about Rudy’s failure to provide discovery. Rudy claims that all his iCloud emails would be in the TrustPoint materials.

All of my [redacted] iCloud data would have also been included in the TrustPoint data because I synced my iCloud to my devices.

But Costello’s declaration reveals that prior to October 18, 2021, he had observed to the Special Master that many of the email files, “contain no ‘body’ text” and by October 18, 2021, he learned that the reason for that is that “this is the way the iPhone stores backup data.”

Rudy’s lawyer, at least, learned before this lawsuit was filed that the TrustPoint material wouldn’t have his emails intact. Nevertheless, Rudy claimed his emails would be available in the TrustPoint materials, and apparently never checked his existing iCloud, Gmail, and ProtonMail accounts for relevant emails.

Meanwhile Costello confirmed something still more damning: that ultimately he and Rudy never appealed any of the designations that the Special Master in that case, Barbara Jones, came to on his content.

Trustpoint would then send me sections of the electronic material, so that I could designate whatever communications I believed were covered by attorney client, work product, or executive privilege. Those identified communications would then be sent to Judge Jones for her ruling. If there was a dispute between Judge Jones and myself, the matter would be referred to Judge J. Paul Oetken, the sitting SDNY Judge who had authorized the search warrants. We never needed to have Judge Oetken resolve a dispute.

That’s important, because we know how many files, total, Barbara Jones ultimately deemed to be privileged: 43.

Remember: per Judge Paul Oetken’s order, this privilege review covered all material post-dating January 1, 2018, regardless of topic.

Here’s what Jones said about the results of her review in a January 22, 2022 filing (filed before this lawsuit moved towards discovery):

As indicated in my November 2, 2021 Report, I initially reserved decision on the first 3 items that were designated as privileged by Mr. Giuliani’s counsel. After further discussions regarding these items, I agree that they are privileged and should not be turned over to the Government’s investigative team.

B. Device 1B05 – Chats and Messages

I next assigned for review the chats and messages that post-dated January 1, 2018 on Device 1B05, which is a cell phone. There were originally 25,481 such items, which later increased to 25,629 after a technical issue involving document attachments was identified. An initial release of non-designated items was made to the Government’s investigative team on November 11, 2021.1

Of the total documents assigned for review, Mr. Giuliani designated 96 items as privileged and/or highly personal. Of those 96 designated items, I agreed that 40 were privileged, Mr. Giuliani’s counsel withdrew the privilege designation over 19, and I found that 37 were not privileged. I shared these determinations with Mr. Giuliani’s counsel, and they indicated that they would not challenge my determination that the 37 items are not privileged. The 40 privileged documents have been withheld from the Government’s investigative team and the remaining 56 were released on January 19, 2022.

43 documents total, across Rudy’s 16 devices, were privileged. Most were on an iPhone referred to as 1B05.

Rudy actually used the device identifiers from the search in his privilege log. Most are from 1B05 — and the Bates numbers show that there were over 21,000 items on that phone.

Indeed, we can see that around 40 really are privileged — because they pertain to Rudy’s own representation by Joe Sibley (indeed, those appear to be the only emails that were preserved).

That says Rudy and Costello already agreed that all the rest of the things in this privilege log (save potentially 3 files) — around 220 of which are just from that one phone — are not privileged.

That is, if you put Costello’s declaration together with Rudy’s, it suggests that Rudy claimed, in the Ruby Freeman lawsuit, that hundreds of things were privileged when he and his attorney had already agreed, before this case moved towards discovery, they were not.

I emailed both Costello and Freeman’s attorney Michael Gottlieb to check whether I understand these details correctly and got no response from either.

Rudy’s Corrupted Devices

In a remarkable set of filings, Robert Costello — Rudy Giuliani’s defense attorney and a key player in the effort to package up a doctored laptop and pitch it as Hunter Biden’s — has provided an explanation for why his client wasn’t charged for doing the bidding of Russian-backed Ukrainians without registering as a foreign agent: Because many of the devices seized on April 28, 2021 were “corrupted” (his word).

Here are the filings:

  • Joe Sibley’s response to Ruby Freeman’s motion for sanctions
  • Robert Costello’s declaration purporting to describe the Special Master process in Rudy’s Ukraine influence-peddling case
  • A nolo contendere declaration from Rudy stipulating that he will not contest that he made the defamatory statements about Ruby Freeman and Shaye Moss or that the statements were false, but preserving his ability to argue the statements were opinion or otherwise protected speech

No contest that Rudy lied

The last of these, Rudy’s nolo contendere declaration, may be an attempt to put all these discovery disputes behind him by simply stipulating that the information he would have turned over had he complied with discovery would show that he made the defamatory claims about Freeman and Moss and there was no basis for them. His stipulation is limited to this case, so could not be used in an 18 USC 241 case against him.

Rudy is attempting to stop digging himself deeper in a hole.

Let’s see where we might go if we dig further, shall we?

Costello blames the government contractor for “corrupting” Rudy’s devices

Costello’s declaration claims that he encountered numerous technical problems with the data on the devices, and attributes those problems to the government’s vendor. Based on having blamed the government’s discovery vendor for any technical problems, he claims it is impossible for Rudy to have spoiled any of the materials on the phones.

In reviewing the materials, I encountered numerous non-user generated files and what I referred to as computer gibberish. In addition, there were many emails that contained the header with the sender and recipient addresses, but no text in the body of the email. With respect to this material, in September and October of 2021, I made inquiries of the Special Master’s electronic discovery people, and they informed me that this was exactly how they received the electronic materials. The Special Master’s lawyers informed me that they had made similar inquiries to the Government and the Government reported that any errors in the production of the electronic data, would have occurred when PAE, the Government vendor, performed their extraction procedure. I have attached some of the contemporaneous communications with the Special Master’s office in September and October of 2021. See Exhibit C attached.

As a result of that information, you can see that the allegations made by Mr. Gottlieb are false and not based upon any factual material. Mr. Giuliani has not spoliated any electronic evidence. What has been produced is what Mr. Giuliani received from the United States Government. Mr. Giuliani has never possessed the electronic materials since they were seized in April 2021. It was, and is, physically impossible for Mr. Giuliani to have spoliated any of this evidence as Mr. Gottlieb claims. [my emphasis]

Later, Costello outright claims that the government “had apparently corrupted some of the files as they were extracting the data,” and then wiped them.

There was no way for Mr. Giuliani or I, to know that the Government had apparently corrupted some of the files as they were extracting the data. Likewise, there was no way for Mr. Giuliani or I, to know, [sic] that when the devices were returned by the FBI, AFTER they concluded there would be no charges forthcoming, that the actual devices would be wiped clean. [my emphasis]

That, Costello claims, is proof that Rudy couldn’t have destroyed any electronic evidence.

In short, there is simply no factual basis for Mr. Gottlieb’s allegations of spoliation. It was physically impossible for Rudy Giuliani to do what Mr. Gottlieb swears to.

Except that’s not clear at all. That’s true because Costello’s own evidence doesn’t support his claim that the government attributed all of this to the vendor. That leaves the possibility that Rudy spoiled the evidence before SDNY seized his phones. If so, Costello’s claim that Rudy couldn’t have spoiled the evidence after Ruby Freeman’s lawsuit, in December 2021, is true, but it doesn’t rule out Rudy or someone else — perhaps his Russian spy friends — spoiling evidence before the search in April 2021, at which point he was already lawyered up for at least the Smartmatic suit.

Costello misrepresents review scope

Before I show that Costello’s own evidence about the evidentiary problems doesn’t support his claims, let me demonstrate something more basic.

Costello repeatedly claims (and Sibley repeats) that the government reviewed 26 years of electronic evidence. It’s true that there was evidence from 26 years on the devices. But as I’ve explained repeatedly, even the government asked to limit the scope of review to everything after January 1, 2018. And that’s what Judge Paul Oetken approved on September 16, 2021.

An email Costello included with his declaration — directing Rudy what to review next — shows that’s what the scope of the review was.

Costello may have a reason he wants to obscure the scope of the review, which I’ll return to. Or it may be that after discovering the “corruption” on Rudy’s phones, FBI’s technical experts had to look further, using a warrant that is not yet public. But at least given the public record, it is not an honest representation of what was reviewed, as distinct from what was extracted.

The corruption found on Rudy’s phones

Based on Costello’s evidence, there were five different problems found with Rudy’s devices:

  • The dates on emails adopted the date of extraction — July 2021 — as the last modified date
  • Some .jpg files could not be viewed
  • Emails from Rudy’s phone lacked the text of the email
  • There were unreadable files on the larger devices
  • The WhatsApp texts had gotten garbled

Costello includes some cherry-picked emails to substantiate those problems. I’ll put them in order.

The first identified problem was the last-modified date, which Costello wrote someone from Trustpoint to identify on September 15 and which I first noted days later. Costello does not mention whether or how that problem was fixed.

Then, Costello quoted from his own email sent on September 30, which described that everything on seven devices was non-readable non-user created.

The bottom line of which is that there is virtually No User Created Info on the first seven devices. The screen shots of data we observed was non- readable non user created data which is clearly non- responsive and so we shouldn’t raise any objections to it being turned over to the Government.

Additionally we are getting the Special Master to go to the Government and its vendor to see if they can eliminate all of the non- user created data from the 9 remaining devices to make our future work more manageable.

A response from the Special Master on October 1, 2021 describes the problems with those seven devices somewhat differently, this way:

  • .jpg files that cannot be viewed
  • missing email/text body issue
  • unreadable “computer files” on the larger devices

Those devices were reviewed for files through seizure, so they likely had contemporaneous records.

Then, an instruction email from the Special Master team, written on October 15, 2021 — regarding the iPhone from which the bulk of the files were turned over — suggests that on that phone only the missing email/text issue remained. This is one of the only communications that describes something the government represented. And at least per them, it’s not a matter of corruption, it’s a matter of how iPhones work.

It is our expectation that these documents can be reviewed quickly, given that many are very short, and others — as you’ve pointed out previously — contain no “body” text. We have asked the Government why many messages do not contain bodies, and their understanding is that this is the way the iPhone stores backup data.

Then, on October 21, 2021, Costello sent an email noting that the WhatsApp texts were muddled.

Trustpoint reports to us that within the field of approximately 25,000 data items there are approximately 7500 “WhatsApp” entries. The way the Government’s expert presented this evidence almost all the Whats App entries consist of garbled words in English. For example the phrase “In God we trust” would likely appear to us now as “God we trust in”.


Frankly we do not know how to deal with this, and we wanted to alert you to his latest glitch which will be found on more than 25% of the items to be searched.

The Special Master responded the following week that they “hope to have a solution shortly.”

As noted above, the Special Master turned over virtually everything on that phone, so they found a way to deal with the WhatsApp issue.

Given the number of files found on the remaining 8 devices, may well have found the same problem on those devices as they did on the first seven.

In short, at least per the record Costello himself provides, he has no evidence the government attributed any of this to the vendor. Costello claimed that the government had told the Special Master that,

the government reported that any errors in the production of the electronic data, would have occurred when PAE, the Government vendor performed their extraction procedure.

But, unless I’m missing it, he provides no evidence of that.

It appears likely that 15 of 16 devices lacked substantive information, and the only thing he provides an explanation for is that some emails — emails that Rudy would have separate access to — weren’t downloaded onto a backup of his phone.

Costello spins on Rudy’s non-compliance on emails

According to Rudy’s own declaration, he helped Trump plot a coup attempt using three different emails, which other documents (including Costello’s own declaration!) reveal must be:

  • rudolphgiuliani at icloud
  • helen0528 at gmail
  • TruthandJustie4U at proton

Rudy’s own privilege log shows that he retained both the gmail and icloud emails — but for things after January 6 and before the seizure, which in the log are fairly presented as privileged.

Rudy’s own privilege log shows none of the protonmail accounts used, even though Bernie Kerik’s does (more on that later).

That’s why it’s so interesting that Costello attacks rather than addresses why Epshteyn (and Christina Bobb) had responsive records that Rudy didn’t turn over.

In paragraph 5 of Mr. Gottlieb’s affirmation, he states that they obtained a December 13, 2020 email from Defendant Giuliani to Boris Ephsteyn [sic] which ” reiterates Defendant’s false claims about Plaintiffs that: “Georgia has video evidence of 30,000 illegal ballots cast after the observers were removed.”” Note first, that the Plaintiffs in in this case were not mentioned, but further note, that when one reviews the citation for this email (ECF-56-7), there is a later email in that same exhibit from Jason Miller that reports: “Statement on hold until further notice, pending Rudy’s talk with the President.” In the spirit of lack of candor, Mr. Gottlieb failed to mention that email.

Here’s the email in question (which redacts which email it went to, but one Bobb turned over was sent to Rudy’s Gmail). But whichever one it came from, it’s an email that Rudy still had access to in 2021, as evidenced by the exhibits presented in this case.

There seems to be good cause to conclude Rudy deleted the email or refused to look for it.

Costello and Sibley’s exaggeration of the investigative closure

Again, 15 of 16 of these devices had some as yet unexplained data that was not user created. I don’t see where Costello substantiated that the government’s vendor did this. Short of doing that, he can’t rule out that Rudy — or, again, the Russian spies he was cozy with at the time — destroyed the data on the devices.

And that’s why I find it notable how Costello and Sibley misrepresent the nature of DOJ’s notice the grand jury investigation into Rudy’s Ukraine influence peddling had concluded.

At the same time as NY State was asking Barbara Jones to serve as the monitor over Trump Organization’s legal woes with the state, SDNY filed this letter, asking Judge Oetken to terminate the appointment of Jones.

The Government writes to notify the Court that the grand jury investigation that led to the issuance of the above-referenced warrants has concluded, and that based on information currently available to the Government, criminal charges are not forthcoming. Accordingly, the Government respectfully requests that the Court terminate the appointment of the Special Master, the Hon. Barbara S. Jones.

As I noted at the time, Costello ran to the press and claimed this meant Rudy would not be charged.

But Costello never claimed to have received a declination letter. And contemporaneous reporting made clear the case remained open.

We now know why: Instead of whatever prosecutors expected to find on at least 7 of Rudy’s phone, they found non-user generated non-readable files. Maybe their vendor fucked up. Maybe something else happened to the devices. But there was nothing there for them to build their case on.

Which is why Costello’s spin on what happened is so interesting. He faults Ruby Freeman’s lawyer for not mentioning that Rudy wasn’t charged.

In his Affirmation, Mr. Gottlieb referenced a criminal investigation run by the SDNY involving Mr. Giuliani, but conveniently failed to mention that it was resolved in Mr. Giuliani’s favor.


First, let me state that after the Government, be it the FBI or the U. S. Attorney’s Office for the Southern District of New York (“SDNY”) reviewed 26 years’  worth of electronic data, the SDNY, [sic] issued an unusual public statement declaring that it was not charging Mr. Giuliani with any violation of federal law.

But he overstates the filing, which only addresses the grand jury in question. And the only reason the statement was unusual is that it wasn’t a declination letter sent to Costello himself.

Given the revelation that at least 7 and possibly as many as 15 of these devices were — to use Costello’s word — “corrupted,” it makes other details of the Rudy investigation more interesting, including a request, reported in April 2022, for help accessing other phones.

If the vendor didn’t “corrupt” the data on 15 of 16 of Rudy’s devices — and I don’t see where Costello shows they did — I can imagine that the SDNY might pursue how they got corrupted.

And that may be why Rudy is attempting to end any further review of why he can’t even find emails that Boris Epshteyn had access to.

Rudy Giuliani Claims He’s Shooting Blank Documents

Ruby Freeman and her daughter Shaye Moss have, as Beryl Howell invited them to do, moved to compel Rudy Giuliani to comply with discovery in their defamation lawsuit. The two 2020 Georgia election workers sued for the damage caused by the lynch mob Rudy summoned by falsely claiming they were attempting to steal votes after he saw a video showing Moss passing her mother a ginger mint.

The motion and all its exhibits are here.

What seems to be happening is that Rudy, having had his phones seized in 2021 and successfully avoided — thus far — charges for his Ukraine influence-peddling, is deliberately slow-walking discovery here to avoid identifying any devices or records that prosecutors can use in that investigation, the Georgia investigation, or Jack Smith’s January 6 one, all while sustaining a story that is already starting to fall apart.

As described in the motion to compel, Rudy’s non-compliance has included:

  • Refusing to turn over any phone or financial records
  • Refusing to explain what accounts and devices he has included in his searches
  • Failing to search for texts and messaging apps from the phones seized in 2021
  • Providing discovery based on much earlier requests from the January 6 Committee and Dominion’s lawsuit against him, rather than the requests from Freeman’s lawyers
  • Providing documents on Hunter Biden along with one Pentagon City Costco receipt
  • Others — like Bernie Kerik and Christina Bobb — similarly refusing to comply
  • Claiming, then disclaiming, reliance on “unknown GOP operatives” for the false claims made about Freeman
  • Refusing to describe how he became aware of the surveillance footage on which he based his false claims about Freeman and Moss

As a reminder, back on April 21, 2021, DOJ obtained a warrant for around 18 of Rudy’s phones in conjunction with the investigation into Rudy’s Ukrainian influence peddling that Bill Barr had successfully obstructed. By September of that year, DOJ had convinced Judge Paul Oetken to have Special Master Barbara Jones to review all the contents on his phones, not just that pertaining to the Ukraine warrants. Since then, I’ve been arguing that DOJ could — and at this point, almost certainly has — obtained that content for use in the January 6 investigation.

Dominion sued Rudy back in 2021. The January 6 Committee subpoenaed Rudy in January 2022 and interviewed him in May 2022. Those are the discovery requests on which Rudy is attempting to rely in this suit, rather than doing searches specific to the requests made by Freeman’s lawyers.

But after May 2022, Rudy’s exposure in Georgia went up. In addition to Freeman’s lawyers filing their amended complaint on May 10, 2022, Fani Willis convened her grand jury on May 2, 2022, subpoenaed Rudy to testify in June 2022, and he testified in August. It is virtually certain that Rudy gave answers to Willis — at the very least, about what he knew of Trump’s call to Brad Raffensperger on January 2 — that subsequent testimony has since disputed and on which topic he has since amended his interrogatory response.

The materials in this motion reveal that Rudy’s lawyer in this matter (Joe Sibley — who represented Christina Bobb in a J6C deposition that conflicts with Rudy’s answers here, though Robert Costello was present for Rudy’s March deposition) at first promised thousands of documents to Freeman’s lawyers, while claiming that most documents would be unavailable because of the Special Master process tied to the Ukraine investigation. Last July 12, Rudy provided 1,269 documents he had also turned over to Dominion’s much earlier request, which Freeman’s lawyers describe as, “his first and only substantial document production to date.”

Then, on August 3, Robert Costello made a showy announcement that SDNY had ended the Special Master process, which is not the same thing as getting a letter that he’s not a subject of that investigation anymore. Shortly thereafter, Freeman’s attorneys pointed out that the excuse Rudy had been using to limit his discovery in this case was no longer operative. He had the phones that — he claimed — included all his communications from the period during which he had started the conspiracy theories about Freeman.

After that showy announcement from Costello on August 3, things changed dramatically. In September, Sibley told Freeman’s lawyers there were 18,000 documents relevant to discovery in the materials seized from his phone. A month later, he said there were 400. In October, Rudy turned over 177 of those documents, 51 of which were blank. Since then, Sibley seems to have provided answer after answer that amounted to throwing up his hands when describing the state of Rudy’s discovery.

Rudy is quite literally attempting to claim he can only shoot blank documents in hopes of getting through this discovery process.

In his March 2023 deposition, Rudy claimed that the physical phones returned by SDNY — which he says only happened in August — were “wiped out.” What actually seems to have happened is that he hasn’t figured out how to access the content saved to the cloud by discovery vendor TrustPoint, and may not have tried to access the phones themselves, which I believe Costello had publicly claimed to have been returned earlier last year.

But far and away the best way to understand his answers are that, first of all, he and Bobb gave materially inconsistent answers while being represented by Sibley, most notably on the topic of whether they participated in the Brad Raffensperger call, which Bobb said they did and Rudy originally claimed — and presumably claimed to Fani Willis’ grand jury — that they had not.

Just as importantly, Rudy may be aware of both messaging apps and phone accounts that he’s not certain prosecutors in SDNY, Georgia, or DC have identified, so he’s refusing to be forthcoming about all the devices and phone accounts he used. There are probably communications from his phones that Costello successfully claimed were privileged during the SDNY Special Master process, which would be obviously crime-fraud excepted in any proceeding before someone who knows the January 6 investigation well. Prosecutors in both SDNY and DC will be able to tell after a quick review of exhibits included with this motion to compel whether Rudy’s claims about the status of the phone content from TrustPoint are accurate.

And therein lies the risk of the game that Rudy is playing.

This would be an obviously bullshit response before any judge, including Carl Nichols (who is presiding over the much more leisurely Dominion suit against Rudy).

But by luck of the draw, he’s attempting this stunt before Beryl Howell, who even on good days does not suffer fools at all, much less gladly, and who until just a month ago was the Chief Judge presiding over all the grand jury proceedings in DC, including the January 6 investigation. She’s one of just two or three judges who knows whether DOJ asked for and obtained a warrant to get the stuff from Rudy’s phones in SDNY. If they did (and I’d bet a very good deal of money they did), she would have seen an affidavit explaining in what form DC USAO understood that phone content to be, and if they did, she has likely overseen discussions about any further attorney-client protections DOJ had to adhere to. If DC USAO obtained warrants for other cloud content, she might also know about any accounts that Rudy is not disclosing to Freeman, including those whose email and phone accounts Rudy consistently used as a proxy. She likely has a sense of how many phone accounts DOJ has identified for Rudy, none of the call records of which would be subject to attorney-client protection. She may know of other aliases that Rudy used in his assault on the election.

Rudy is pulling this contemptuous stunt in front of the one judge who may know the extent to which he’s bullshitting.

Which may be why, at a few points in Freeman’s Motion to Compel, her attorneys note that they’re only asking for modest relief, basically just leverage to get Rudy to actually answer the questions, as well as attorney fees for their time he has wasted.

But Judge Howell? Well, if she wants to use her discretion to provide expanded relief, Freeman’s lawyers say, they’d be open to that too.

The relief Plaintiffs seek in this Motion is narrow, while recognizing that the Court in its discretion may enter additional forms of relief, including sanctions. Plaintiffs reserve all rights relating to seeking expanded forms of relief in the future.

At this point, there are at least two criminal investigations into Rudy and two civil suits — January 6, Georgia, Dominion, and this suit. Even before reviewing his J6C transcript, it’s easy to identify plenty of ways his evolving answers here, amended in part because of inconsistent testimony given before the J6C, conflict with what he must have answered before the Georgia grand jury, which could start issuing indictments any day.

Juggling all that legal exposure would be difficult for a sober, organized man with little real legal exposure.

For Rudy, though, this insane approach may be, at best, a futile attempt to limit the damage this civil case can do to his criminal exposure.